As filed with the Securities and Exchange            Registration No. 333-108099
Commission on September 2, 2003.


                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


                                 AMENDMENT NO. 1
                                       TO
                                    FORM S-4


                             REGISTRATION STATEMENT
                                      UNDER
                           THE SECURITIES ACT OF 1933

                         WINTRUST FINANCIAL CORPORATION
             (EXACT NAME OF REGISTRANT AS SPECIFIED IN ITS CHARTER)


                                                                       
           ILLINOIS                            6022                          36-3873352
(State or Other Jurisdiction of     (Primary Standard Industrial           (I.R.S. Employer
Incorporation or Organization)      Classification Code Number)        Identification Number)

                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096
    (Address, Including Zip Code, and Telephone Number, Including Area Code,
                  of Registrant's Principal Executive Offices)

                                DAVID A. DYKSTRA
           SENIOR EXECUTIVE VICE PRESIDENT AND CHIEF OPERATING OFFICER
                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096
            (Name, Address, Including Zip Code, and Telephone Number,
                   Including Area Code, of Agent for Service)

                                   COPIES TO:

                                                     
       JENNIFER R. EVANS, ESQ.                          DENNIS R. WENDTE, ESQ.
VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.   BARACK FERRAZZANO KIRSCHBAUM PERLMAN & NAGELBERG LLC
 222 NORTH LASALLE STREET, SUITE 2600            333 WEST WACKER DRIVE, SUITE 2700
      CHICAGO, ILLINOIS 60601                          CHICAGO, ILLINOIS 60606
          (312) 609-7500                                    (312) 984-3100

                         ------------------------------
         APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: As
soon as practicable after the Registration Statement becomes effective.

                         ------------------------------


         If the securities being registered on this Form are being offered in
connection with the formation of a holding company and there is compliance with
General Instruction G, check the following box. |_|

         If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following box
and list the Securities Act registration statement number of the earlier
effective registration statement for the same offering. |_|

         If this Form is a post-effective amendment filed pursuant to Rule
462(d) under the Securities Act, check the following box and list the Securities
Act registration statement number of the earlier effective registration
statement for the same offering. |_|


                         ------------------------------


         THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE
OR DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT
SHALL FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(a) OF
THE SECURITIES ACT OF 1933, AS AMENDED, OR UNTIL THE REGISTRATION STATEMENT
SHALL BECOME EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID
SECTION 8(a), MAY DETERMINE.



The information in this proxy statement is not complete and may be changed. We
may not offer or sell these securities until the registration statement filed
with the Securities and Exchange Commission is effective. This proxy statement
is not an offer to sell these securities and it is not soliciting an offer to
buy these securities in any state where the offer or sale is not permitted.


                       SUBJECT TO COMPLETION, DATED SEPTEMBER 2, 2003



ADVANTAGE NATIONAL BANCORP, INC.                  WINTRUST FINANCIAL CORPORATION
LOGO                                                                        LOGO

                                ----------------

                          PROXY STATEMENT OF ADVANTAGE

                                ----------------

                             PROSPECTUS OF WINTRUST

                                ----------------

                  Merger Proposed - Your Vote Is Very Important

DEAR ADVANTAGE SHAREHOLDERS:


         You are cordially invited to attend a Special Meeting of Shareholders
of Advantage National Bancorp, Inc. which will be held on September 30, 2003, at
10:00 a.m. at the offices of Advantage National Bank, 75 East Turner Avenue,
Elk Grove Village, Illinois 60007.

         At the meeting, you will be asked to approve the merger agreement
between Advantage and Wintrust Financial Corporation that provides for
Wintrust's acquisition of Advantage. If the merger is completed, each share of
Advantage common stock you own will be valued at $26.50 and converted into the
right to receive shares of Wintrust's common stock based on an average price for
Wintrust's common stock over a period of time prior to the merger, as described
in this proxy statement/prospectus. If the average price determined at closing
for Wintrust common stock is $35.00 or more, you would receive 0.757 shares of
Wintrust common stock for each share of Advantage common stock you own.

         Wintrust's  common stock is traded on the Nasdaq  National Market under
the symbol "WTFC." The closing price of Wintrust common stock on August 28, 2003
was $35.51.


         The merger cannot be completed unless a majority of the holders of
Advantage common stock approve the merger agreement. YOUR BOARD OF DIRECTORS HAS
UNANIMOUSLY APPROVED THE MERGER AGREEMENT AND RECOMMENDS THAT YOU APPROVE IT.


         Additional information regarding the transaction, the merger agreement,
Advantage and Wintrust is set forth in the attached proxy  statement/prospectus.
This document also serves as the  prospectus  for the 989,909 shares of Wintrust
common stock that were  registered  by Wintrust for use in  connection  with the
merger.  WE URGE YOU TO READ THIS ENTIRE  DOCUMENT  CAREFULLY,  INCLUDING  "RISK
FACTORS" BEGINNING ON PAGE 13.


                                        Sincerely,


                                        /s/ Gerhardt E. Umlauf

                                        Gerhardt E. Umlauf
                                        President of
                                        Advantage National Bancorp, Inc.

NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
REGULATORY BODY HAS APPROVED OR DISAPPROVED OF THE SECURITIES TO BE ISSUED UNDER
THIS PROXY STATEMENT/PROSPECTUS OR DETERMINED IF THIS PROXY STATEMENT/PROSPECTUS
IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL
OFFENSE.

THE SECURITIES TO BE ISSUED IN CONNECTION WITH THE MERGER ARE NOT SAVINGS OR
DEPOSIT ACCOUNTS OR OTHER OBLIGATIONS OF ANY BANK OR NONBANK SUBSIDIARY OF ANY
OF THE PARTIES, AND THEY ARE NOT INSURED BY THE FEDERAL DEPOSIT INSURANCE
CORPORATION, THE BANK INSURANCE FUND OR ANY OTHER GOVERNMENTAL AGENCY.


THIS PROXY STATEMENT/PROSPECTUS IS DATED SEPTEMBER 2, 2003, AND IS FIRST BEING
MAILED TO ADVANTAGE SHAREHOLDERS ON OR ABOUT SEPTEMBER 2, 2003.






                              AVAILABLE INFORMATION

         This document incorporates certain important business and financial
information about Wintrust from other documents that are not included in or
delivered with this document. These documents are available to you without
charge upon your written or oral request. Your requests for these documents
should be directed to the following:

                         WINTRUST FINANCIAL CORPORATION
                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
                           ATTENTION: DAVID A. DYKSTRA
                             CHIEF OPERATING OFFICER
                                 (847) 615-4096


         IN ORDER TO ENSURE TIMELY DELIVERY OF THESE DOCUMENTS, YOU SHOULD MAKE
YOUR REQUEST BY SEPTEMBER 15, 2003 TO RECEIVE THEM BEFORE THE SPECIAL MEETING.

         YOU CAN ALSO OBTAIN DOCUMENTS INCORPORATED BY REFERENCE IN THIS
DOCUMENT THROUGH THE SEC'S WEBSITE AT WWW.SEC.GOV. SEE "WHERE YOU CAN FIND MORE
INFORMATION" BEGINNING ON PAGE 41.






                        ADVANTAGE NATIONAL BANCORP, INC.

                              75 East Turner Avenue
                        Elk Grove Village, Illinois 60007


                       -----------------------------------

                    Notice of Special Meeting of Shareholders


                           to be Held September 30, 2003


                       -----------------------------------



Date:    September 30, 2003

Time:    10:00 a.m.

Place:   Advantage National Bank
         75 East Turner Avenue
         Elk Grove Village, Illinois 60007



To Advantage National Bancorp, Inc. Shareholders:

We are pleased to notify you and invite you to the Special Meeting of
Shareholders. At the meeting you will be asked to vote on the following matters:

          o         Approval of the Agreement and Plan of Merger, dated July 2,
                    2003, that provides for Wintrust Financial Corporation to
                    acquire Advantage, as described in the attached proxy
                    statement/prospectus.

          o         To transact any other business that properly comes before
                    the Special Meeting, or any adjournments or postponements of
                    the Special Meeting.


Holders of record of Advantage common stock at the close of business on
August 22, 2003 may vote at the meeting. Approval of the merger agreement
requires the affirmative vote at the meeting of a majority of the issued and
outstanding shares of Advantage common stock.


THE BOARD OF DIRECTORS OF ADVANTAGE UNANIMOUSLY RECOMMENDS THAT YOU VOTE "FOR"
APPROVAL OF THE MERGER AGREEMENT.

To ensure that your shares are voted at the Special Meeting, please promptly
complete, sign and return the proxy form in the enclosed envelope.


                                              By Order of the Board of Directors



                                              /s/ Gerhardt E. Umlauf
                                              --------------------------------
                                              Gerhardt E. Umlauf
                                              President



Elk Grove Village, Illinois
September 2, 2003







                                TABLE OF CONTENTS


                                                                                                               PAGE
                                                                                                              
Questions and Answers About the Merger...........................................................................1

Summary..........................................................................................................3

Information about Wintrust and Advantage.........................................................................3
         Historical Comparative Per Share Data; Pro Forma Per Share Data.........................................8
         Selected Financial Data of Wintrust....................................................................10

Risk Factors....................................................................................................13
         There is fluctuation in the trading market of Wintrust's common stock and the market price of
                  the common stock you will receive in the merger is uncertain..................................13
         The anticipated benefits of the merger may never be realized...........................................13
         Advantage's shareholders will not control Wintrust's future operations.................................13
         De novo operations and branch openings impact Wintrust's profitability.................................14
         Wintrust's allowance for loan losses may prove to be insufficient to absorb losses that may
                  occur in its loan portfolio...................................................................14
         Wintrust's premium finance business involves unique operational risks and could expose it to
                  significant losses............................................................................14
         Wintrust may be adversely affected by interest rate changes............................................15
         Wintrust's future success is dependent on its ability to compete effectively in the highly
                  competitive banking industry..................................................................15
         Wintrust's business may be adversely affected by the highly regulated environment in which it
                  operates......................................................................................15
         Since Wintrust's business is concentrated in the Chicago metropolitan area, a downturn in the
                  Chicago economy may adversely affect its business.............................................16
         Wintrust's shareholder rights plan and provisions in its articles of incorporation and by-laws
                  may delay or prevent an acquisition of Wintrust by a third party..............................16

Caution About Forward-Looking Statements........................................................................17

Special Meeting of Advantage Shareholders.......................................................................18
         Date, Place, Time and Purpose..........................................................................18
         Record Date, Voting Rights, Quorum and Required Vote...................................................18
         Voting and Revocability of Proxies.....................................................................18
         Dissenters' Rights.....................................................................................18

Description of the Merger.......................................................................................20
         General  ..............................................................................................20
         Background of the merger...............................................................................20
         Wintrust's reasons for the merger......................................................................21
         Advantage's reasons for the merger and recommendation of the Board of Directors........................22
         Accounting treatment...................................................................................23
         Tax consequences of the merger.........................................................................23
         Regulatory Approvals...................................................................................25
         Interests of certain persons in the merger.............................................................25
         Voting agreements......................................................................................26
         Restrictions on resale of Wintrust common stock........................................................26

Description of the Merger Agreement.............................................................................26
         Time of completion.....................................................................................26
         Consideration to be received in the merger.............................................................27
         Exchange of certificates...............................................................................28
         Conduct of business pending the merger and certain covenants...........................................28
         Representations and warranties.........................................................................29
         Conditions to completion of the merger.................................................................31








                                TABLE OF CONTENTS
                                  (continued)
                                                                                                               PAGE
                                                                                                              
         Termination............................................................................................32
         Termination fee........................................................................................32
         Management and operations after the merger.............................................................32
         Employee benefit matters...............................................................................32
         Expenses...............................................................................................32
         Nasdaq stock listing...................................................................................33

Comparison of Shareholder Rights................................................................................33
         Authorized capital stock...............................................................................33
         Payment of dividends...................................................................................33
         Advance notice requirements for presentation of business and nominations of directors at annual
                  meetings of shareholders......................................................................33
         Quorum.................................................................................................34
         Election, classification and size of Board of Directors................................................34
         Removal of directors...................................................................................34
         Filling vacancies on the Board of Directors............................................................34
         Amendment of Articles of Incorporation and By-laws.....................................................34
         Mergers, acquisitions and other transactions...........................................................35
         Business combinations with interested shareholders.....................................................35
         Limitations on directors' liability....................................................................35
         Indemnification........................................................................................36
         Action by shareholders without a meeting...............................................................36
         Special meetings of shareholders.......................................................................36
         Preemptive rights......................................................................................36
         Appraisal rights of dissenting shareholders............................................................36
         Certain anti-takeover effects of Wintrust's articles and by-laws and Illinois law......................36
         Rights Plan............................................................................................37

Business of Wintrust............................................................................................38
         Recent Developments....................................................................................38

Business of Advantage...........................................................................................39

Legal Matters...................................................................................................40

Experts.........................................................................................................40

Shareholder Proposals...........................................................................................40

Where You Can Find More Information.............................................................................40

Incorporation of Certain Information by Reference...............................................................41



Annex A:  Agreement and Plan of Merger.........................................................................A-1

Annex B:  Illinois Dissenters' Rights Law......................................................................B-1

Annex C:  Form of Voting Agreement.............................................................................C-1




                                       ii





                     QUESTIONS AND ANSWERS ABOUT THE MERGER

Q:       WHAT AM I BEING ASKED TO VOTE ON? WHAT IS THE PROPOSED TRANSACTION?

A:       You are being asked to vote on the approval of a merger agreement that
         provides for the acquisition of Advantage by Wintrust. Wintrust will
         own all of Advantage's outstanding common stock after the merger is
         completed and you will become a shareholder of Wintrust.

Q:       WHAT WILL I BE ENTITLED TO RECEIVE IN THE MERGER?


A:       If the merger is completed, each share of Advantage common stock you
         own will be valued at $26.50 and converted into the right to receive
         shares of Wintrust common stock based on an average price for
         Wintrust's common stock over a period of time prior to the merger. See
         "Summary -- What Advantage shareholders will receive" on page 5.


Q:       WHY DO ADVANTAGE AND WINTRUST WANT TO MERGE?

A:       Advantage believes the proposed merger will provide Advantage
         shareholders with substantial benefits, and Wintrust believes that the
         merger will further its strategic growth plans. The products and
         markets of Advantage and Wintrust generally are complementary and the
         combined company should be able to better serve customers and compete
         more effectively within its market. To review the reasons for the
         merger in more detail, see "Description of the Merger -- Wintrust's
         reasons for the merger" on page 21 and "Description of the Merger --
         Advantage's reasons for the merger and recommendation of the Board of
         Directors" on page 22.

Q:       WHAT DOES THE ADVANTAGE BOARD OF DIRECTORS RECOMMEND?


A:       Advantage's Board of Directors unanimously recommends that you vote
         "FOR" adoption of the merger agreement. Advantage's Board of Directors
         has determined that the merger agreement and the merger are fair to and
         in the best interests of Advantage and its shareholders. To review the
         background and reasons for the merger in greater detail, see pages 20
         to 23.


Q:       WHAT VOTE IS REQUIRED TO ADOPT THE MERGER AGREEMENT?


A:       Holders of a majority of the outstanding shares of Advantage common
         stock must vote in favor of the merger. All of the officers and
         directors of Advantage and Advantage National Bank have agreed to vote
         their shares of Advantage common stock, comprising approximately 37% of
         the shares entitled to vote at the meeting, in favor of the merger at
         the Special Meeting. Wintrust shareholders will not be voting on the
         merger agreement.


Q:       WHAT DO I NEED TO DO NOW?  HOW DO I VOTE?

A:       After you have carefully read and considered the information contained
         in this proxy statement/prospectus, please complete, sign, date and
         mail your proxy form in the enclosed return envelope as soon as
         possible. This will enable your shares to be represented at the
         meeting. You may also vote in person at the meeting. If you do not
         return a properly executed proxy form and do not vote at the Special
         Meeting, this will have the same effect as a vote against the approval
         of the merger agreement. If you sign, date and send in your proxy form,
         but you do not indicate how you want to vote, your proxy will be voted
         in favor of approval of the merger agreement.

Q:       WHAT IF I OPPOSE THE MERGER?  DO I HAVE DISSENTERS' RIGHTS?

A:       Advantage shareholders who do not vote in favor of the merger agreement
         and otherwise comply with all of the procedures of Sections 11.65 and
         11.70 of the Illinois Business Corporation Act will be entitled to
         receive payment in cash of the estimated fair value of their shares of
         Advantage common stock as ultimately determined under the statutory
         process. A copy of these provisions is attached as Annex B to this
         proxy statement/prospectus. This value could be more but could also be
         less than the merger consideration.


                                       1



Q:       CAN I CHANGE MY VOTE OR REVOKE MY PROXY AFTER I HAVE MAILED MY SIGNED
         PROXY FORM?

A:       Yes. Until exercised at the Special Meeting, you can revoke your proxy
         and change your vote in any of the following ways:

         o        by filing with the secretary of Advantage a duly executed
                  revocation of proxy;

         o        by submitting a new proxy form with a later date; or

         o        by voting in person at the Special Meeting.

          You may  request a new proxy form by  calling  Gerhardt  E.  Umlauf at
          Advantage at (847) 364-0100.

Q:       WHAT ARE THE TAX CONSEQUENCES OF THE MERGER TO ME?

A:       In general, the exchange of your shares of Advantage common stock for
         Wintrust common stock will be tax-free for United States federal income
         tax purposes. However, you will recognize gain on cash received instead
         of fractional shares of Wintrust's common stock and in exchange for
         your warrants to purchase Advantage common stock, if any. You should
         consult with your tax adviser for the specific tax consequences of the
         merger to you. See "Description of the Merger - Tax consequences of the
         merger" on page 23.

Q:       SHOULD I SEND IN MY STOCK CERTIFICATES NOW?

A:       No. Either at the time of closing or shortly after the merger is
         completed, Wintrust's exchange agent will send you a letter of
         transmittal with instructions informing you how to send in your stock
         certificates to the exchange agent. You should use the letter of
         transmittal to exchange your Advantage stock certificates for new
         certificates representing the shares of Wintrust common stock you will
         own after the merger is complete. DO NOT SEND IN YOUR STOCK
         CERTIFICATES WITH YOUR PROXY FORM.

Q:       WHEN IS THE MERGER EXPECTED TO BE COMPLETED?

A:       We will try to complete the merger as soon as possible. Before that
         happens, the merger agreement must be approved and adopted by
         Advantage's shareholders and we must obtain the necessary regulatory
         approvals. Assuming shareholders vote at least a majority of
         Advantage's outstanding shares of common stock in favor of the approval
         and adoption of the merger agreement and we obtain the other necessary
         approvals, we expect to complete the merger during the fourth quarter
         of 2003.

Q:       WHAT IS THE PURPOSE OF THIS DOCUMENT?

A:       This document serves as both a proxy statement of Advantage and a
         prospectus of Wintrust. As a proxy statement, this document is being
         used to solicit your proxy to vote in favor of the merger agreement at
         the Special Meeting. As a prospectus, it is being provided because
         Wintrust is offering to exchange shares of its common stock for your
         shares of Advantage common stock when the merger is completed.

Q:       WHO CAN ANSWER MY OTHER QUESTIONS?

A:       If you have more questions about the merger or how to submit your
         proxy, or if you need additional copies of this proxy
         statement/prospectus or the enclosed proxy form, you should contact
         Advantage's president, Gerhardt E. Umlauf, at (847) 364-0100.



                                       2



                                     SUMMARY


         This Section highlights selected information in this proxy
statement/prospectus and may not contain all of the information important to
you. To understand the merger more fully, you should read this entire document
carefully, including the annexes and the documents referred to in this proxy
statement/prospectus. A list of the documents incorporated by reference appears
on page 41.


INFORMATION ABOUT WINTRUST AND ADVANTAGE


WINTRUST FINANCIAL CORPORATION  (See page 39)
727 North Bank Lane
Lake Forest, Illinois  60045
(847) 615-4096

         Wintrust Financial Corporation, an Illinois corporation, is a financial
holding company headquartered in Lake Forest, Illinois. Wintrust operates seven
community banks, primarily in affluent suburbs of Chicago, which provide
community-oriented, personal and commercial banking services primarily to
individuals and small to mid-size businesses through 32 banking facilities. As
of June 30, 2003, Wintrust had consolidated total assets of $4.1 billion,
deposits of $3.4 billion and shareholders' equity of $249.4 million.  Wintrust's
common stock trades on the Nasdaq National Market under the symbol "WTFC."

ADVANTAGE  (See page 40)
75 East Turner Avenue
Elk Grove Village, Illinois 60007
(847) 364-0100

         Advantage, an Illinois corporation, is a bank holding company. Its
primary business is operating its bank subsidiary, Advantage National Bank, a
nationally chartered bank with offices in Elk Grove Village and Roselle,
Illinois, that was opened in January 2001. As of June 30, 2003, Advantage had
consolidated total assets of $107.5 million, deposits of $95.6 million and
shareholders' equity of $9.4 million. There is no established trading market for
Advantage shares.


THE MERGER AND THE MERGER AGREEMENT  (See page 27)

         The acquisition of Advantage by Wintrust is governed by a merger
agreement. The merger agreement provides that, if all of the conditions are
satisfied or waived, a newly formed subsidiary of Wintrust will be merged with
and into Advantage. After the consummation of the merger, Advantage will become
a wholly-owned subsidiary of Wintrust. We encourage you to read the merger
agreement, which is included as Annex A to this proxy statement/prospectus.


REASONS FOR THE MERGER  (See pages 20 to 23)


         The Board of Directors of Advantage unanimously determined that the
merger agreement and the merger consideration were fair to and in the best
interests of Advantage and its shareholders and unanimously recommends that
holders of Advantage common stock vote in favor of the approval and adoption of
the merger agreement and the transactions contemplated by the merger agreement.

         In its deliberations and in making its determination, with the
assistance of its legal and financial advisors, Advantage's Board of Directors
considered many factors including, without limitation, the following:

         o        its knowledge of the business, operations, properties, assets,
                  competitive position, financial condition, operating results,
                  management, strategic objectives and prospects of Advantage;

         o        developments relating to consolidation and additional
                  competition within the U.S. banking industry in general and in
                  the Chicago metropolitan market in particular, and Advantage's
                  position as a "community" bank in the communities of Elk Grove
                  Village and Roselle, Illinois;


                                       3



         o        other possible alternatives to the merger, including
                  continuing to operate Advantage, and the perceived risks and
                  uncertainties attendant to Advantage's execution of its
                  strategic growth plans as an independent banking organization,
                  including the need to access additional capital and enhance
                  its technology platform on a cost-effective basis to support
                  future growth;

         o        the value of the shares of Wintrust common stock comprising
                  the merger consideration, the formula that calculates the
                  merger consideration at the effective time, and the fact that
                  Wintrust common stock is traded on Nasdaq Stock Market and has
                  substantially greater liquidity than the shares of Advantage
                  common stock;

         o        information concerning the business, financial condition, and
                  results of operations of Wintrust, including recent
                  performance of Wintrust common stock; and

         o        its view as to the likelihood of the willingness of a third
                  party to pay more for Advantage, and the ability of Advantage
                  to agree to this type of transaction, despite the merger
                  agreement and the voting agreements.

         Wintrust's Board of Directors believes that the merger is in the best
interests of Wintrust and its shareholders. Wintrust's Board of Directors has
approved the merger agreement. In deciding to approve the merger agreement, the
Wintrust Board of Directors considered a number of factors, including:

         o        management's  view that the acquisition of Advantage  provides
                  an attractive opportunity to expand into the northwest Chicago
                  metropolitan area, which they consider a desirable market;

         o        the  community  banking   orientation  of  Advantage  and  the
                  compatability of Advantage with Wintrust and its subsidiaries;

         o        a  review  of  the   demographic,   economic   and   financial
                  characteristics  of the markets in which  Advantage  operates,
                  including  existing and potential  competition  and history of
                  the market areas with respect to financial institutions;

         o        management's review of the business, operations,  earnings and
                  financial condition, including capital levels and asset
                  quality, of Advantage since its de novo formation in 2001; and

         o        the  likelihood  of regulators  approving  the merger  without
                  undue conditions or delay.

         The Boards of Directors of both Wintrust and Advantage believe that the
merger will result in expanded resources for profitable growth and that the
combined resources of Wintrust and Advantage will provide greater ability to
compete in the changing and increasingly competitive financial services
industry, including increasing the availability of and access to additional
financial services and products for its customers.

BOARD RECOMMENDATION TO ADVANTAGE SHAREHOLDERS  (See page 22)

         Advantage's Board of Directors believes that the merger of Advantage
with Wintrust is in the best interests of Advantage and Advantage's
shareholders. ADVANTAGE'S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU
VOTE "FOR" THE MERGER.

ADVANTAGE SPECIAL MEETING  (See page 18)


         The Special Meeting will be held at Advantage National Bank, located at
75 East Turner Avenue, Elk Grove Village, Illinois 60007, on September 30, 2003,
at 10:00 a.m., Chicago time. Advantage's Board of Directors is soliciting
proxies for use at the Special Meeting. At the Special Meeting, Advantage
shareholders will be asked to vote on a proposal to approve the merger
agreement.



                                       4



RECORD DATE FOR THE SPECIAL MEETING; REVOCABILITY OF PROXIES (See page 18)


         You may vote at the Special Meeting if you own shares of Advantage
common stock of record at the close of business on August 22, 2003. You will
have one vote for each share of Advantage common stock you owned on that date.
You may revoke your proxy at any time before the vote at the Special Meeting.


VOTE REQUIRED  (See page 18)

         To approve the merger, a majority of the outstanding shares of
Advantage common stock must be voted in favor of the merger agreement at the
Special Meeting. Therefore, shareholders holding a majority of the outstanding
shares of Advantage common stock entitled to vote at the Special Meeting must be
present in person or by proxy at the Special Meeting. Shareholders may vote
their shares in person at the Special Meeting or by executing and returning the
enclosed proxy form.


         All of the officers and directors of Advantage and Advantage National
Bank have committed to vote their shares of Advantage common stock in favor of
the merger. At the record date, the directors and executive officers of
Advantage owned 269,026 shares of Advantage common stock, constituting
approximately 37% of the total number of outstanding shares of Advantage common
stock at that date. See "Description of the Merger -- Voting agreements" on page
24.


WHAT ADVANTAGE SHAREHOLDERS WILL RECEIVE  (See page 27)

         Under the merger agreement, for each share of Advantage common stock
you own, Wintrust will pay you the number of shares of Wintrust common stock
equal to $26.50 divided by the average price of Wintrust common stock during the
pricing period, which is defined as the unweighted average high and low sales
prices of Wintrust common stock on the Nasdaq National Market during the pricing
period. This number is referred to as the "exchange ratio."  The pricing period
is the period of 10 trading days ending two trading days before the merger is
completed. If the average price is within the range of $25.00 to $35.00, the
higher the average price, the fewer shares you will receive and the lower the
average price, the more shares you will receive, so that the value of the shares
you are to receive in the merger will be $26.50 based on the actual average
price during the pricing period. Outside this price range, there are certain
limitations in the merger agreement, as described below, that affect the number
of shares you receive in the merger.


         If the average price of Wintrust common stock during the pricing period
is greater than $35.00 per share, the exchange ratio will still be computed as
$26.50 divided by $35.00 so that the number of shares of Wintrust common stock
to be issued to you will never be less than the number you would receive if the
average price during the pricing period is $35.00. This means that the value at
closing of the shares you are to receive in the merger would be more than $26.50
based on the actual average price during the pricing period.

         If the average price of Wintrust common stock during the pricing period
is less than $25.00 per share, the exchange ratio will be $26.50 divided by
$25.00 so that the number of shares of Wintrust common stock to be issued to you
will never be more than the number of shares you would receive if the average
price during the pricing period is $25.00. This means that the value of the
shares you are to receive in the merger would be less than $26.50 based on the
actual average price during the pricing period.


         Advantage shareholders will not receive fractional shares of Wintrust
common stock. Instead, they will receive a cash payment for any fractional
shares based on the value of Wintrust common stock determined in the manner
described above.

         Once the merger is complete, Illinois Stock Transfer Company,
Wintrust's exchange agent, will mail you materials and instructions for
exchanging your Advantage stock certificates for Wintrust stock certificates.
You should not send in your Advantage stock certificates until you receive the
transmittal materials and instructions from the exchange agent.


                                       5



REGULATORY APPROVALS  (See page 25)


         The merger cannot be completed until Wintrust receives the regulatory
approval of the Board of Governors of the Federal Reserve System, commonly known
as the Federal Reserve. Wintrust has submitted a notice filing to The Federal
Reserve Bank of Chicago seeking the requisite approval of the merger. In
approving the merger, the Federal Reserve may impose conditions or restrictions.
If any of these conditions or restrictions are objectionable to Wintrust, the
Board of Directors of Wintrust may choose to terminate the merger.


NEW WINTRUST SHARES WILL BE ELIGIBLE FOR TRADING ON NASDAQ  (See page 33)

         The shares of Wintrust common stock to be issued in the merger can be
traded on the Nasdaq National Market.

CONDITIONS TO THE MERGER  (See page 31)

         The completion of the merger is subject to the fulfillment of a number
of conditions, including:

         o        approval of the merger agreement at the Special Meeting by a
                  majority of the outstanding shares of Advantage common stock;


         o        approval of the transaction by the Federal Reserve and
                  expiration or termination of all waiting periods required by
                  law; and


         o        the representations and warranties made by the parties in the
                  merger agreement must be materially true and correct as of the
                  effective date of the merger or as otherwise required in the
                  merger agreement.

TERMINATION  (See page 32)

         Subject to conditions and circumstances described in the merger
agreement, either Wintrust or Advantage may terminate the merger agreement if,
among other things, any of the following occur:


         o        the merger is not completed by December 31, 2003 (or March 31,
                  2004 if there is a delay due to regulatory approval);


         o        any condition to the merger has become impossible to satisfy;

         o        the other party has materially breached the agreement and has
                  failed to cure the breach;

         o        the holders of a majority of Advantage common stock do not
                  approve the merger; or

         o        in certain circumstances if Advantage has received a superior
                  offer to sell to a third party.

TERMINATION FEE  (See page 33)

         Under certain circumstances described in the merger agreement, Wintrust
may demand a $1,000,000 termination fee from Advantage if the transaction is not
consummated.

INTERESTS OF OFFICERS AND DIRECTORS IN THE MERGER THAT ARE DIFFERENT THAN YOURS
(See page 25)

         You should be aware that some Advantage directors may have interests in
the merger that are different from, or in addition to, their interests as
shareholders. Advantage's Board of Directors was aware of these interests and
took them into account in approving the merger. The merger contains a provision
requiring Wintrust to provide continuing indemnification to Advantage directors
and officers.


                                       6




VOTING AGREEMENTS  (See page 26)

         Officers and directors of Advantage and Advantage National Bank owning
a total of approximately 37% of the outstanding shares of Advantage common stock
on the record date have agreed to vote all of their shares of common stock in
favor of the merger agreement at the Special Meeting. These agreements terminate
if the merger agreement is terminated in accordance with its terms. A copy of
the form of voting agreement is attached to this proxy statement/prospectus as
Annex C.


ACCOUNTING TREATMENT OF THE MERGER  (See page 23)

         The merger will be accounted for as a purchase transaction in
accordance with accounting principles generally accepted in the United States.


CERTAIN DIFFERENCES IN SHAREHOLDER RIGHTS  (See page 33)


         When the merger is completed, Advantage shareholders, whose rights are
governed by Illinois law and Advantage's articles of incorporation and by-laws,
automatically will become Wintrust shareholders, and their rights will continue
to be governed by Illinois law, as well as Wintrust's articles of incorporation
and by-laws, in addition to laws and requirements that apply to public
companies.

DISSENTERS' RIGHTS  (See page 18)

         Advantage shareholders may dissent to the merger and, upon following
the requirements of Illinois law, receive cash in the amount of the fair value
of their shares instead of shares of Wintrust common stock.

         A copy of the sections of the Illinois Business Corporation Act
pertaining to dissenters' rights is attached as Annex B to this proxy
statement/prospectus. You should read the statute carefully and consult with
your legal counsel if you intend to exercise these rights.

TAX CONSEQUENCES OF THE MERGER  (See page 23)

         Your receipt of the merger consideration generally will be tax-free for
United States federal income tax purposes, except to the extent you receive cash
instead of fractional shares of Wintrust common stock and cash in exchange for
warrants to purchase shares of Advantage common stock, if any. You should
consult your tax adviser for a full understanding of the federal, state, local
and foreign tax consequences of the merger to you.





                                       7




HISTORICAL COMPARATIVE PER SHARE DATA; PRO FORMA PER SHARE DATA

         The table below shows the reported high and low sales prices of
Wintrust's common stock during the periods indicated. This information gives
effect to a 3-for-2 stock split, effected in the form of a 50% stock dividend,
as of March 14, 2002.




                                                    HIGH             LOW
                                                    ----             ---
                                                               
YEAR ENDED DECEMBER 31, 2001
   First Quarter..........................          $12.75           $10.54
   Second Quarter.........................           17.62            11.67
   Third Quarter..........................           21.41            16.27
   Fourth Quarter.........................           22.13            17.93
YEAR ENDED DECEMBER 31, 2002
   First Quarter..........................          $22.99           $18.33
   Second Quarter.........................           34.58            22.22
   Third Quarter..........................           36.00            26.54
   Fourth Quarter.........................           32.66            25.45
YEAR-TO-DATE 2003
   First Quarter..........................          $33.65           $27.19
   Second Quarter.........................           32.40            27.74
   Third Quarter (through August 28, 2003).          36.18            29.30




         The following table presents selected comparative per share data for
Wintrust common stock and Advantage common stock on a historical and pro forma
combined basis, giving effect to the merger using the purchase method of
accounting. The information included in the table below for Advantage at
December 31, 2002 is based on per share data for the common stock of Advantage
National Bank. Amounts at June 30, 2003 reflect per share data for Advantage
National Bancorp, Inc.

         The pro forma combined information is not necessarily indicative of the
actual results that would have occurred had the merger been consummated at the
beginning of the periods indicated, or of the future operations of the combined
entity.




                                                SIX MONTHS ENDED          YEAR ENDED
                                                  JUNE 30, 2003       DECEMBER 31, 2002
                                                ----------------      -----------------
                                                                     
WINTRUST HISTORICAL:
   Diluted earnings per share.............          $    0.94              $    1.60
   Cash dividends declared per share......               0.08                   0.12
   Book value per share (at period end)...              14.31                  13.19
WINTRUST PRO FORMA COMBINED:
   Diluted earnings per share.............          $    0.92              $    1.54
   Cash dividends declared per share......               0.08                   0.12
   Book value per share (at period end)...              14.95                  13.86
ADVANTAGE HISTORICAL:
   Diluted earnings per share.............          $    0.23              $   (0.12)
   Cash dividends declared per share......                --                      --
   Book value per share (at period end)...              12.86                  12.85
ADVANTAGE PRO FORMA COMBINED(1):
   Diluted earnings per share.............          $    0.69              $    1.17
   Cash dividends per share...............               0.06                   0.09
   Book value per share (at period end)...              11.31                  10.49


---------------------------
(1)      Computed using an exchange ratio of 0.757, which is based on an
         assumed Wintrust common stock value of $35.01, the closing price of
         Wintrust common stock on August 27, 2003.





                                       8




         The following table sets forth the last sales prices as reported by
Nasdaq for Wintrust common stock on the dates indicated, and the equivalent per
share value for Advantage common stock, giving effect to the merger as of the
same dates:




                                                     HISTORICAL
                                CLOSING PRICE          PRICE             ADVANTAGE
                                   WINTRUST          ADVANTAGE        EQUIVALENT PER
                                 COMMON STOCK       COMMON STOCK        SHARE VALUE
                                -------------       ------------      --------------
                                                                  
July 1, 2003(1)...........           $30.03              (2)               $26.50
August 28, 2003...........           $35.51              (2)               $26.89



---------------------------
(1)      Trading date preceding the date of public announcement of the proposed
         merger.
(2)      There is no  established  trading  market for the shares of  Advantage.
         During 2000,  in connection  with the de novo  formation of  Advantage's
         bank subsidiary,  Advantage National Bank sold shares to investors at a
         price equivalent to $15.00 per share of Advantage common stock.




                                       9



SELECTED FINANCIAL DATA OF WINTRUST


         The summary consolidated financial data presented below as of or for
each of the years in the five-year period ended December 31, 2002, are derived
from Wintrust's audited historical financial statements. The summary data
presented below as of or for the six-month periods ended June 30, 2003 and 2002,
are derived from unaudited consolidated financial statements. In Wintrust's
opinion, all adjustments, consisting only of normal recurring adjustments,
necessary for a fair statement of results as of or for the six-month periods
have been included. Per share amounts have been adjusted to reflect the 3-for-2
stock split effected as a stock dividend effective as of March 14, 2002. This
information should be read in conjunction with "Management's Discussion and
Analysis of Financial Condition and Results of Operations" and the consolidated
financial statements and the notes thereto incorporated by reference into this
prospectus from Wintrust's Annual Report on Form 10-K for the fiscal year ended
December 31, 2002, and Wintrust's Quarterly Report on Form 10-Q for the period
ended June 30, 2003. Results for past periods are not necessarily indicative of
results that may be expected for any future period, and results for the
six-month period ended June 30, 2003 are not necessarily indicative of results
that may be expected for the entire year ending December 31, 2003.



                                SIX MONTHS ENDED
                                    JUNE 30,                            YEARS ENDED DECEMBER 31,
                           -----------------------  ---------------------------------------------------------------
                             2003(1)      2002(2)     2002(2)       2001          2000         1999         1998
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
                                                   (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS)
                                                                                    
STATEMENT OF INCOME
   DATA:
Total interest income..    $   96,504   $   86,509  $  182,233   $  166,455    $  148,184   $  109,331   $   87,979
Total interest expense.        41,572       39,924      84,105       92,441        87,184       61,597       51,215
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
   Net interest income.        54,932       46,585      98,128       74,014        61,000       47,734       36,764
Provision for loan
   losses..............         5,493        4,831      10,321        7,900         5,055        3,713        4,297
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
   Net interest income
      after provision
      for loan losses..        49,439       41,754      87,807       66,114        55,945       44,021       32,467
Non-interest Income:
   Gain on sale of
      premium finance
      receivables......         2,270        1,594       3,374        4,564         3,831        1,033           --
   Fees on mortgage
      loans sold.......         9,142        3,951      12,259        7,831         2,911        3,206        5,569
   Wealth management
      fees.............        12,953       12,001      25,229        1,996         1,971        1,171          788
   Service charges on
      deposit accounts.         1,722        1,491       3,121        2,504         1,936        1,562        1,065
   Administrative
      services revenues         2,159        1,753       3,501        4,084         4,402          996           --
   Premium finance
      defalcation-partial
      settlement(3)....            --        1,250       1,250           --            --           --           --
   Securities (losses)
      gains, net.......           606         (153)        107          337           (40)           5           --
   Other...............         7,996        4,636      11,831        7,482         3,295        1,835          653
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
      Total non-interest
        income.........        36,848       26,523      60,672       28,798        18,306        9,808       8,075
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------

(See footnotes on page 12)



                                       10






                                SIX MONTHS ENDED
                                    JUNE 30,                            YEARS ENDED DECEMBER 31,
                           -----------------------  ---------------------------------------------------------------
                             2003(1)      2002(2)     2002(2)       2001          2000         1999         1998
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
                                                   (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS)
                                                                                    
Non-interest Expense:
   Salaries and
      employee benefits    $   35,715   $   28,762  $   63,442   $   35,628    $   28,119   $   20,808   $   18,944
   Equipment expense...         3,758        3,526       7,191        6,297         5,101        3,199        2,221
   Occupancy expense,
      net..............         3,785        3,153       6,691        4,821         4,252        2,991        2,435
   Data processing.....         2,079        2,056       4,161        3,393         2,837        2,169        1,676
   Advertising and
      marketing........         1,043        1,057       2,302        1,604         1,309        1,402        1,612
   Professional fees...         1,704        1,296       2,801        2,055         1,681        1,203        1,654
   Amortization of
      intangibles......           298          117         324          685           713          251          120
   Premium finance
      defalcation(3)...            --           --          --           --         4,320           --           --
   Other non-interest
      expenses.........        11,038        8,618      19,072       11,300         9,471        7,655        7,171
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
      Total
        non-interest
        expense........        59,420       48,585     105,984       65,783        57,803       39,678       35,833
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
Income before taxes
   and cumulative
   effective of
   accounting change...        26,867       19,692      42,495       29,129        16,448       14,151        4,709
Income tax expense
   (benefit)...........         9,585        7,023      14,620       10,436         5,293        4,724       (1,536)
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
Income before
   cumulative effect
   of accounting change        17,282       12,669      27,875       18,693        11,155        9,427        6,245
Cumulative effect of
   change in
   accounting for
   derivatives, net of
   tax.................            --           --          --         (254)           --           --           --
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
   Net income..........    $   17,282   $   12,669  $   27,875   $   18,439    $   11,155   $    9,427   $    6,245
                           ==========   ==========  ==========   ==========    ==========   ==========   ==========
COMMON SHARE DATA:
Earnings per share:
   Basic...............    $     1.00   $     0.82  $     1.71   $     1.34    $     0.85   $     0.76   $     0.51
   Diluted.............          0.94         0.77        1.60         1.27          0.83         0.73         0.49
Cash dividends per
   common share(4).....          0.08         0.06        0.12         0.093         0.067          --           --
Book value per share...         14.31        12.15       13.19         9.72          7.92         7.06         6.15
Weighted average
   common shares
   outstanding:
   Basic...............        17,360       15,513      16,334       13,734        13,066       12,373       12,212
   Diluted.............        18,473       16,526      17,445       14,545        13,411       12,837       12,742
SELECTED FINANCIAL
   CONDITION DATA (AT
   END OF PERIOD):
Total assets...........    $4,132,394   $3,219,400  $3,721,555   $2,705,422    $2,102,806   $1,679,382   $1,348,048
Total loans............     2,896,148    2,308,945   2,556,086    2,018,479     1,547,596    1,270,126      974,031
Total deposits.........     3,419,946    2,608,507   3,089,124    2,314,636     1,826,576    1,463,622    1,229,154
Notes payable..........        26,000       58,650      44,025       46,575        27,575        8,350           --
Subordinated notes.....        50,000           --      25,000           --            --           --           --
Long term debt - trust
   preferred securities        76,816       51,050      50,894       51,050        51,050       31,050       31,050
Total shareholders'
   equity..............       249,399      205,999     227,002      141,278       102,276       92,947       75,205



(See footnotes on following page)


                                       11






                                SIX MONTHS ENDED
                                    JUNE 30,                            YEARS ENDED DECEMBER 31,
                           -----------------------  ---------------------------------------------------------------
                             2003(1)      2002(2)     2002(2)       2001          2000         1999         1998
                           ----------   ----------  ----------   ----------    ----------   ----------   ----------
                                                                                    
SELECTED FINANCIAL
   RATIOS AND OTHER
   DATA:
Performance Ratios:
   Non-interest income
      to average
      assets(5)........          1.92%        1.85%       1.89%        1.24%         0.99%        0.66%        0.69%
   Non-interest
      expense to
      average
      assets(3)(5).....          3.10         3.38        3.30         2.83          3.12         2.65         3.04
   Net overhead
      ratio(3)(5)(6)...          1.18         1.54        1.41         1.59          2.13         2.00         2.36
   Return on average
      assets(3)(5).....          0.90         0.88        0.87         0.79          0.60         0.63         0.53
   Return on average
      equity(3)(5).....         14.74        15.85       14.76        15.24         11.51        11.58         8.68
   Average
      loan-to-average
      deposit ratio....          86.1         90.4        88.5         87.4          87.7         86.6         80.1
   Dividend payout
      ratio(4)(5)......           8.5          7.7         7.5          7.4           8.0           --           --
Asset Quality Ratios:
   Non-performing
      loans to total
      loans............          0.47%        0.48%       0.49%        0.64%         0.63%        0.55%        0.56%
   Allowance for loan
      losses to:
      Total loans......          0.74         0.69        0.72         0.68          0.67         0.69         0.72
      Non-performing
        loans..........        156.42       143.39      146.63       105.63        107.75       126.10       129.66
   Net charge-offs to
      average
      loans(3)(5)......          0.19         0.23        0.24         0.26          0.24         0.19         0.28
   Non-performing
      assets to total
      assets...........          0.35         0.37        0.34         0.48          0.46         0.41         0.45
Other data at end of
   period:
   Number of banking
      facilities.......            32           31          31           29            28           24           21

---------------------------
(1)      Wintrust completed its acquisition of Lake Forest Capital Management
         Company on February 1, 2003. The results for the six months ended June
         30, 2003 include the results of Lake Forest Capital Management Company
         since that date.
(2)      Wintrust completed its acquisition of the Wayne Hummer Companies
         effective as of February 1, 2002. The results for the six months ended
         June 30, 2002 and year ended December 31, 2002 include the results of
         the Wayne Hummer Companies since February 1, 2002.
(3)      In 2000, Wintrust recorded a $4.3 million pre-tax charge ($2.6 million
         after-tax) related to a fraudulent loan scheme perpetrated against its
         premium finance subsidiary. The amount of this charge was not included
         in loans charged-off because a lending relationship had never been
         established. In the first quarter of 2002, Wintrust recovered $1.25
         million (pre-tax) of this amount ($754,000 after-tax).
(4)      Wintrust declared its first semi-annual dividend payment in January
         2000. Dividend data reflected for the interim periods reflect
         semi-annual, not quarterly, dividends.
(5)      Certain financial ratios for interim periods have been annualized.
(6)      Non-interest expense less non-interest income divided by average total
         assets.







                                       12



                                  RISK FACTORS


         In addition to the other information contained in or incorporated by
reference into this proxy statement/prospectus, including the matters addressed
under the caption "Caution About Forward-Looking Statements" on page 17, you
should consider the following risk factors carefully in deciding whether to vote
for the adoption of the merger agreement.



         THERE IS FLUCTUATION IN THE TRADING MARKET OF WINTRUST'S COMMON STOCK
AND THE MARKET PRICE OF THE COMMON STOCK YOU WILL RECEIVE IN THE MERGER IS
UNCERTAIN.


         You will receive Wintrust common stock in the merger. The number of
shares you receive will depend on the average price of Wintrust common stock
prior to the merger. Changes in the market price of Wintrust common stock may
result from a variety of factors, including general market and economic
conditions, the future financial condition and operating results of Wintrust,
changes in Wintrust's businesses, operations and prospects and regulatory
considerations, many of which are beyond Wintrust's control.

         The price of Wintrust common stock at completion of the merger may vary
from its price on the date the merger agreement was signed, from its price on
the date of this proxy statement/prospectus, from its price on the date of the
Special Meeting and from the average price during the 10-day pricing period used
to determine the number of shares you are to receive. You will not be entitled
to receive additional cash or shares in the merger if the price of Wintrust
common stock on the closing date of the merger is less than the average price
during the pricing period. Because the merger will be completed after the date
of the Special Meeting, at the time of the Special Meeting you will not know
what the market value of the Wintrust common stock you will receive after the
merger will be. See "Description of the Merger Agreement -- Consideration to be
received in the merger."


         Wintrust's common stock is traded on the Nasdaq National Market under
the symbol "WTFC". The maintenance of an active public trading market depends,
however, upon the existence of willing buyers and sellers, the presence of which
is beyond Wintrust's control or the control of any market maker. In addition to
the shares of Wintrust common stock to be issued in the merger, Wintrust plans
to issue up to a maximum of approximately 360,000 additional shares of its
common stock in its pending acquisition of Village Bancorp, Inc., expected to
close during 2003, and up to an additional 1,150,000 shares of common stock in a
capital raising transaction during 2003. Wintrust also has shares of common
stock covered by resale registration statements and estimates that there are
currently approximately 665,000 of those shares outstanding that have not yet
been resold. These remaining shares may be freely sold from time to time in the
market. The market price of Wintrust's common stock could drop significantly if
shareholders sell or are perceived by the market as intending to sell large
blocks of its shares.


THE ANTICIPATED BENEFITS OF THE MERGER MAY NEVER BE REALIZED.

         The success of the merger will depend partly on Wintrust's ability to
successfully integrate the business and operations of Advantage with those of
Wintrust. As Advantage National Bank matures, in order for Wintrust to recognize
the anticipated operational efficiencies, it will have to successfully grow the
operations of the bank. This growth may be inhibited by a lack of synergies
between the customers, employees or operations of the two companies, as well as
the inability to successfully introduce its customers to new and existing
products and services. Uncertainties exist in integrating the business of
Advantage into Wintrust and these benefits may never be realized.

ADVANTAGE'S SHAREHOLDERS WILL NOT CONTROL WINTRUST'S FUTURE OPERATIONS.

        Together,  Advantage's shareholders own 100% of Advantage and have
absolute power to approve or reject any matters requiring  shareholder  approval
under Illinois law and Advantage's articles of incorporation and by-laws.  After
the merger,  Advantage  shareholders  will become  owners of less than 5% of the
outstanding  shares of  Wintrust  common  stock.  Even if all  former  Advantage
shareholders  voted together on all matters  presented to Wintrust  shareholders
from time to time, the former Advantage  shareholders most likely would not have
a significant  impact on the approval or rejection of future Wintrust  proposals
submitted to a shareholder vote.


                                       13




DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT WINTRUST'S PROFITABILITY.

         Wintrust's financial results have been and will continue to be impacted
by its strategy of de novo bank formations and branch openings. Wintrust has
employed this strategy to build an infrastructure that management believes can
support additional internal growth in its banks' respective markets. Wintrust
expects to open its eighth de novo bank in late 2003, and expects to undertake
additional de novo bank formations or branch openings as it expands into
additional communities in and around Chicago. In addition, Wintrust's pending
acquisitions involve relatively recently formed de novo banks. Based on
Wintrust's experience, its management believes that it generally takes from 13
to 24 months for new banks to first achieve operational profitability, depending
on the number of branch facilities opened, the impact of organizational and
overhead expenses, the start-up phase of generating deposits and the time lag
typically involved in redeploying deposits into attractively priced loans and
other higher yielding earning assets. However, it may take longer than expected
or than the amount of time Wintrust has historically experienced for new banks
and/or branch facilities to reach profitability, and there can be no guarantee
that these new banks or branches will ever be profitable. To the extent Wintrust
undertakes additional de novo bank and branch formations, its level of
reported net income, return on average equity and return on average assets will
be impacted by start-up costs associated with such operations, and it is likely
to continue to experience the effects of higher expenses relative to operating
income from the new operations. These expenses may be higher than Wintrust
expected or than its experience has shown.

WINTRUST'S ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB
LOSSES THAT MAY OCCUR IN ITS LOAN PORTFOLIO.

         Wintrust's allowance for loan losses is established in consultation
with management of its operating subsidiaries and is maintained at a level
considered adequate by management to absorb loan losses that are inherent in the
portfolios. At June 30, 2003, Wintrust's allowance for loan losses was 156.42%
of total nonperforming loans and 0.74% of total loans. The amount of future
losses is susceptible to changes in economic, operating and other conditions,
including changes in interest rates, that may be beyond its control, and such
losses may exceed current estimates. Rapidly growing and de novo bank loan
portfolios are, by their nature, unseasoned. As a result, estimating loan loss
allowances for Wintrust's newer banks is more difficult, and therefore the banks
may be more susceptible to changes in estimates, and to losses exceeding
estimates, than banks with more seasoned loan portfolios. Although management
believes that the allowance for loan losses is adequate to absorb losses that
may develop in Wintrust's existing portfolios of loans and leases, there can be
no assurance that the allowance will prove sufficient to cover actual loan or
lease losses in the future.

WINTRUST'S PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND COULD
EXPOSE IT TO SIGNIFICANT LOSSES.

         Of Wintrust's total loans at June 30, 2003, 22%, or $625.8 million,
were comprised of commercial insurance premium finance receivables that it
generates through First Insurance. These loans, intended to enhance the average
yield of earning assets of its banks, involve a different, and possibly higher,
level of risk of delinquency or collection than generally associated with loan
portfolios of more traditional community banks. First Insurance also faces
unique operational and internal control challenges due to the relatively rapid
turnover of the premium finance loan portfolio and high volume of new loan
originations. The average term to maturity of these loans is less than 12
months, and the average loan size when originated is approximately $30,000.

         Because Wintrust conducts lending in this segment primarily through
relationships with a large number of unaffiliated insurance agents and because
the borrowers are located nationwide, risk management and general supervisory
oversight may be more difficult than in its banks. Wintrust may also be more
susceptible to third party fraud. Acts of fraud are difficult to detect and
deter, and Wintrust cannot assure investors that its risk management procedures
and controls will prevent losses from fraudulent activity. For example, in the
third quarter of 2000, Wintrust recorded a non-recurring after-tax charge of
$2.6 million in connection with a series of fraudulent loan transactions
perpetrated against First Insurance by one independent insurance agency located
in Florida. Although Wintrust has since enhanced its internal controls system at
First Insurance, it may continue to be exposed to the risk of significant loss
in its premium finance business.

         Due to continued growth in origination volume of premium finance
receivables, since the second quarter of 1999, Wintrust has been selling some of
the loans First Insurance originates to an unrelated third party. Wintrust has

                                       14


recognized gains on the sales of the receivables, and the proceeds of sales have
provided it with additional liquidity. Consistent with its strategy to be asset
driven, Wintrust expects to pursue similar sales of premium finance receivables
in the future; however, it cannot assure you that there will continue to be a
market for the sale of these loans and the extent of Wintrust's future sales of
these loans will depend on the level of new volume growth in relation to its
capacity to retain the loans within its subsidiary banks' loan portfolios.
Because Wintrust has a recourse obligation to the purchaser of premium finance
loans that it sells, it could incur losses in connection with the loans sold if
collections on the underlying loans prove to be insufficient to repay to the
purchaser the principal amount of the loans sold plus interest at the negotiated
buy-rate and if the collection shortfall on the loans sold exceeds Wintrust's
estimate of losses at the time of sale.


WINTRUST MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.


         Wintrust's interest income and interest expense are affected by general
economic conditions and by the policies of regulatory authorities, including the
monetary policies of the Federal Reserve. Changes in the economic environment
may influence the growth rate of loans and deposits, the quality of the loan
portfolio and loan and deposit pricing. While Wintrust has taken measures
intended to manage the risks of operating in a changing interest rate
environment, there can be no assurance that such measures will be effective in
avoiding undue interest rate risk. For example, due to historically low
prevailing interest rates, beginning in late 2001, Wintrust moved to an
asset/liability position intended to benefit it in a rising rate scenario. As
interest rates declined further over the last 18 months, Wintrust has suffered
compression in its net interest margin as a result of this strategy. However,
the significant decline in interest rates to historic lows has also led to
significant increases in mortgage loan origination volume since 2001. Wintrust
recorded fees on mortgage loans sold of $9.1 million in the first six months of
2003 and $12.3 million in 2002, compared to $7.8 million in 2001. This source of
non-interest income is likely to decline in periods of rising interest rates.

         The success of Wintrust's covered call option program, which Wintrust
has used in effect to hedge its interest rate risk, may also be affected by
changes in interest rates. With the decline in interest rates over the last two
years to historically low levels, Wintrust has been able to augment the total
return of its investment securities portfolio by selling call options on
fixed-income securities it owns. Wintrust recorded fee income of $6.0 million
during 2002 compared to $4.3 million in 2001, from premiums earned on these
covered call option transactions. In a rising interest rate environment,
particularly if the yield curve remains steep, the amount of premium income
Wintrust earns on these transactions will likely decline. In addition, Wintrust
has decreased its covered call option activity as rates have increased recently,
and expects to limit this program in a rising rate environment.


WINTRUST'S FUTURE SUCCESS IS DEPENDENT ON ITS ABILITY TO COMPETE EFFECTIVELY IN
THE HIGHLY COMPETITIVE BANKING INDUSTRY.


         The financial services business is highly competitive, and Wintrust
encounters strong direct competition for deposits, loans and other financial
services in all of its market areas. In recent years, several major bank holding
companies have entered or expanded in the Chicago metropolitan market and are
pursuing aggressive branching initiatives in the area. Generally, these
financial institutions are significantly larger than Wintrust and have greater
access to capital and other resources. Wintrust's ability to compete effectively
in the marketplace is also dependent on its ability to adapt successfully to
technological changes within the banking and financial services industries.


WINTRUST'S BUSINESS MAY BE ADVERSELY AFFECTED BY THE HIGHLY REGULATED
ENVIRONMENT IN WHICH IT OPERATES.


         Wintrust is subject to extensive federal and state legislation,
regulation and supervision. The burden of regulatory compliance has increased
under current legislation and banking regulations and is likely to continue to
have or may have a significant impact on the financial services industry. Recent
legislative and regulatory changes, as well as changes in enforcement policies
and capital adequacy guidelines, are increasing Wintrust's costs of doing
business and, as a result, may create an advantage for Wintrust's competitors
who may not be subject to similar legislative and regulatory requirements. In
addition, future regulatory changes, including changes to regulatory capital
requirements, could have an adverse impact on Wintrust's future results. Self
regulatory organizations, such as the New York Stock Exchange and the National
Association of Securities Dealers, require Wintrust's securities brokerage
subsidiaries to comply with extensive rules and regulations, and Wintrust could
be adversely affected by applicable changes in these regulations.


                                       15


SINCE WINTRUST'S BUSINESS IS CONCENTRATED IN THE CHICAGO METROPOLITAN AREA, A
DOWNTURN IN THE CHICAGO ECONOMY MAY ADVERSELY AFFECT ITS BUSINESS.

         Currently, Wintrust's lending and deposit gathering activities are
concentrated primarily in the greater Chicago metropolitan area. Wintrust's
success depends on the general economic condition of Chicago and its
surrounding areas. Declining economic conditions could reduce Wintrust's growth
rate, impair its ability to collect loans, and generally affect its financial
condition and results of operations.




WINTRUST'S   SHAREHOLDER   RIGHTS  PLAN  AND   PROVISIONS  IN  ITS  ARTICLES  OF
INCORPORATION  AND BY-LAWS MAY DELAY OR PREVENT AN  ACQUISITION OF WINTRUST BY A
THIRD PARTY.

         Wintrust's  board of directors has  implemented  a  shareholder  rights
plan.  The rights,  which are attached to Wintrust's  shares and trade  together
with  its  common  stock,  have  certain  anti-takeover  effects.  The  plan may
discourage  or make it more  difficult for another party to complete a merger or
tender offer for Wintrust's shares without  negotiating with Wintrust's board of
directors or to launch a proxy  contest or to acquire  control of a larger block
of Wintrust's shares. If triggered,  the rights will cause substantial  dilution
to a person or group that attempts to acquire  Wintrust  without approval of its
board of directors,  and under certain  circumstances,  the rights  beneficially
owned by the person or group may become void.  The plan also may have the effect
of limiting shareholder participation in certain transactions such as mergers or
tender  offers  whether  or not such  transactions  are  favored  by  Wintrust's
incumbent  directors  and key  management.  In  addition,  Wintrust's  executive
officers  may be more  likely to retain  their  positions  with the company as a
result of the plan,  even if their removal  would be beneficial to  shareholders
generally.

         Wintrust's  articles of incorporation  and by-laws contain  provisions,
including a staggered board  provision,  that make it more difficult for a third
party to gain  control or acquire  Wintrust  without the consent of its board of
directors. These provisions also could discourage proxy contests and may make it
more difficult for dissident  shareholders to elect representatives as directors
and take other corporate actions.

         These provisions of Wintrust's  governing documents may have the effect
of delaying,  deferring or preventing a transaction  or a change in control that
might be in the best interest of Wintrust's shareholders.


                                       16



                    CAUTION ABOUT FORWARD-LOOKING STATEMENTS

         Certain statements contained in this document, including information
incorporated into this document by reference, that are not historical facts may
constitute forward-looking statements within the meaning of Section 27A of the
Securities Act of 1933, as amended, or the Securities Act, and Section 21E of
the Securities Exchange Act of 1934, as amended, or the Securities Exchange Act,
and are intended to be covered by the safe harbor provisions of the Private
Securities Litigation Reform Act of 1995. The sections of this document which
contain forward-looking statements include, but are not limited to, "Questions
and answers about the merger," "Summary," "Risk Factors," "Description of the
merger -- Background of the merger," "Description of the merger -- Wintrust's
reasons for the merger," and "Description of the merger -- Advantage's reasons
for the merger and recommendation of the Board of Directors." You can identify
these statements from our use of the words "may," "will," "should," "could,"
"would," "plan," "potential," "estimate," "project," "believe," "intend,"
"anticipate," "expect," "target" and similar expressions. These forward-looking
statements include statements relating to:

         o        Wintrust's goals, intentions and expectations;

         o        Wintrust's business plans and growth strategies; and

         o        estimates of Wintrust's risks and future costs and benefits.


         These forward-looking statements are subject to significant risks,
assumptions and uncertainties, including among other things, changes in general
economic and business conditions and the risks and other factors set forth in
the "Risk Factors" section beginning on page 13.


         Because of these and other uncertainties, Wintrust's actual results,
performance or achievements, or industry results, may be materially different
from the results indicated by these forward-looking statements. In addition,
Wintrust's past results of operations do not necessarily indicate Wintrust's
future results. You should not place undue reliance on any forward-looking
statement, which speak only as of the date they were made. Wintrust will not
update these forward-looking statements, even though its situation may change in
the future, unless Wintrust is obligated to do so under the federal securities
laws. Wintrust qualifies all of its forward-looking statements by these
cautionary statements.


         Further information on other factors which could affect the financial
results of Wintrust before and after the merger is included in Wintrust's
filings with the Securities and Exchange Commission, or SEC, incorporated by
reference into this proxy statement/prospectus. See "Where You Can Find More
Information" on page 40.



                                       17



                    SPECIAL MEETING OF ADVANTAGE SHAREHOLDERS

DATE, PLACE, TIME AND PURPOSE


         Wintrust's and Advantage's boards of directors are sending you this
proxy statement/prospectus and proxy form to use at the Special Meeting. At the
Special Meeting, the Advantage board of directors will ask you to vote on a
proposal to approve the merger. Advantage and Wintrust will share the costs
associated with the solicitation of proxies for the Special Meeting. The Special
Meeting will be held at Advantage National Bank, 75 East Turner Avenue,
Elk Grove Village, Illinois 60007, on September 30, 2003, at 10:00 a.m., Chicago
time.


RECORD DATE, VOTING RIGHTS, QUORUM AND REQUIRED VOTE


         Advantage has set the close of business on August 22, 2003, as the
record date for determining the holders of Advantage common stock entitled to
notice of and to vote at the Special Meeting. Only Advantage shareholders at the
close of business on the record date are entitled to notice of and to vote at
the Special Meeting.

         The approval of the merger agreement will require the affirmative vote
of at least a majority of the outstanding shares of Advantage. As of the record
date, there were 729,386 shares of Advantage common stock entitled to vote at
the Special Meeting. There must be at least a majority of the outstanding shares
of Advantage present in person or by proxy at the Special Meeting in order for
the vote on the merger to occur. Certain executive officers and directors of
Advantage, whose aggregate ownership represents approximately 37% of the
outstanding shares of Advantage on the record date, have committed to vote their
shares of Advantage common stock in favor of the merger. Wintrust holds no
shares of Advantage common stock.


         Abstentions from voting will have the same effect as voting against the
merger agreement.

VOTING AND REVOCABILITY OF PROXIES

         You may vote in person at the Special Meeting or by proxy. To ensure
your representation at the Special Meeting, we recommend you vote by proxy even
if you plan to attend the Special Meeting. You can always change your vote at
the Special Meeting.

         Voting instructions are included on your proxy form. If you properly
complete and timely submit your proxy, your shares will be voted as you have
directed. You may vote for, against, or abstain with respect to the approval of
the merger. If you are the record holder of your shares and submit your proxy
without specifying a voting instruction, your shares will be voted "FOR"
approval of the merger agreement.

         You may revoke your proxy before it is voted by:

         o        filing with the secretary of Advantage a duly executed
                  revocation of proxy;

         o        submitting a new proxy with a later date; or

         o        voting in person at the Special Meeting.


         Attendance at the Special Meeting will not, in and of itself,
constitute a revocation of a proxy. All written notices of revocation and other
communication with respect to the revocation of proxies should be addressed to:
Advantage National Bank, 75 East Turner Avenue, Elk Grove Village, Illinois
60007, Attention: Gerhardt E. Umlauf.


DISSENTERS' RIGHTS

         Under Illinois law, you are entitled to exercise dissenters' rights and
obtain a cash payment for your shares as a result of Wintrust's acquisition of
Advantage, provided that you comply with the provisions of Sections 11.65 and
11.70 of the Illinois Business Corporation Act, or the IBCA. A copy of those
sections are attached as Annex C and incorporated in this proxy
statement/prospectus by reference. If you comply with the provisions of Section
11.70 of the IBCA, then upon consummation of the merger, you are entitled to
receive payment from Wintrust for the fair value of your shares, with accrued
interest. The term "fair value" means the value of the shares


                                       18



immediately before the merger closing excluding any appreciation or depreciation
in anticipation of the merger, unless the exclusion would be inequitable. If
Wintrust and you cannot agree on the fair value of your shares or the accrued
interest, then the IBCA provides for a judicial determination of these amounts.
The value determined by an Illinois court may be more or less than the value you
are entitled to under the merger agreement. If you desire to exercise
dissenters' rights, you should refer to the statute in its entirety and should
consult with legal counsel before taking any action to ensure that you comply
strictly with the applicable statutory provisions.

         In summary, to exercise dissenters' rights, you must do all of the
following:

         o        deliver to Advantage a written demand for payment of your
                  shares before the vote on the merger is taken;

         o        not vote in favor of the merger; note, however, that a vote,
                  in person or by proxy, against approval and adoption of the
                  merger agreement will not constitute a written demand for
                  appraisal; and

         o        continue to hold your shares of Advantage common stock through
                  the effective time of the merger.

         Your failure to vote against the proposal to adopt the merger agreement
will not constitute a waiver of your dissenters' rights under the IBCA. Also, a
vote against approval of the merger agreement will not by itself be sufficient
to satisfy your obligations if you are seeking an appraisal. You must follow the
procedures set forth in Section 11.70 of the IBCA to obtain dissenters' rights.

         Each outstanding share of Advantage common stock for which a legally
sufficient demand in accordance with Section 11.70 of the IBCA has been made and
that was not voted in favor of approval of the merger will, after the effective
time of the merger, represent only the rights of a dissenting shareholder under
the IBCA. This includes the right to obtain payment for the estimated fair value
of those shares as provided under the IBCA.

         If you make a legally sufficient demand, within ten days after the
effective date of the merger or 30 days after you have delivered your written
demand for payment, whichever is later, Wintrust will send to you a statement
setting forth its opinion as to the fair value of your shares, as well as
certain financial statements and a commitment to pay to you the estimated fair
value for your shares. If you do not agree with the opinion of Wintrust as to
the estimated fair value of the shares, then within 30 days of your receipt of
Wintrust's valuation statement, you must notify Wintrust of your estimated fair
value of your shares and demand the difference between your estimated fair value
and the amount of the payment by Wintrust.

         If, within 60 days from delivery of Wintrust's notice to the dissenting
shareholders, you and Wintrust have not agreed in writing to the fair value of
the shares, Wintrust either will pay the difference in value demanded by you, or
file a petition in the circuit court requesting the court to determine the fair
value of the shares. Wintrust will be required to then make all dissenters to
the merger a party to this proceeding. If Wintrust does not commence the action,
you are permitted by law to commence an action.

         In a proceeding brought by Wintrust to determine value, the court will
determine the costs of the proceeding, including the reasonable compensation of
expenses of the appraisers appointed by the court and excluding fees and
expenses of counsel and experts for the respective parties. If the fair value of
the shares as determined by the court materially exceeds the price that Wintrust
estimated to be the fair value of the shares or if no estimate was given, then
all or any part of the costs may be assessed against Wintrust. If the amount
that any dissenter estimated to be the fair value of the shares materially
exceeds the fair value of the shares as determined by the court, then all or any
part of the costs may be assessed against that dissenter. The costs may be
awarded to the dissenter if the court finds that Wintrust did not substantially
comply with the procedure to dissent in the statute. In addition, costs can be
assessed against either party if the court finds that that party acted
arbitrarily or not in good faith with respect to the dissenter's rights.

         A share for which you have properly exercised your dissenters' rights
and followed the correct procedures in the IBCA will not be converted into, or
represent, a right to receive Wintrust common stock and cash as provided under
the merger agreement. Any of these shares will not, after the effective time of
the merger, be entitled to vote for any purpose or receive any dividends or
other distributions. If, however, you, as the holder of the shares, fail to
properly perfect, effectively withdraw, waive or lose, or otherwise become
ineligible to exercise dissenting


                                       19



                            DESCRIPTION OF THE MERGER

shareholder's rights under the IBCA, then at that time the shares held by you
will be converted into Wintrust common stock as provided in the merger
agreement.

         The following information describes certain aspects of the merger. The
merger agreement, which you should read carefully, is attached as Annex A to
this proxy statement/prospectus.

GENERAL

         When the merger is consummated, Wintrust Merger Co., a subsidiary which
is 100% owned by Wintrust, will merge with and into Advantage. Advantage will be
the surviving entity and will be 100% owned by Wintrust. At the effective time
of the merger, each share of Advantage common stock automatically will be
converted into and exchanged for the right to receive the number of shares of
Wintrust common stock equal to $26.50 divided by the average price of Wintrust
common stock during the pricing period. This number is referred to as the
"exchange ratio." The pricing period is the ten consecutive trading days ending
two trading days before consummation of the merger, and the average price of
Wintrust common stock is defined as the unweighted average high and low sales
prices of Wintrust common stock on the Nasdaq National Market during this
period. The determination of the number of shares of Wintrust common stock to be
issued is subject to possible adjustment as described in the following two
paragraphs.

         If the average price of Wintrust common stock during the pricing period
is greater than $35.00 per share, the exchange rate will be $26.50 divided by
$35.00 for purposes of determining the number of shares of Wintrust common stock
to be issued to each former Advantage shareholder. If the average price of
Wintrust common stock during the pricing period is less than $25.00 per share,
the exchange ratio will be $26.50 divided by $25.00 for purposes of determining
the number of shares of Wintrust common stock to be issued to each former
Advantage shareholder.

         Cash also will be paid instead of any fractional share interests in
Wintrust common stock. Shares of Advantage common stock held by Advantage
shareholders who elect to exercise their dissenters' rights will not be
converted into Wintrust common stock.

BACKGROUND OF THE MERGER

         In late March 2003, one of Advantage's directors was contacted by a
representative of Wintrust who invited him and another director to a meeting
with Wintrust's chairman of the board to discuss Wintrust's potential interest
in affiliating with Advantage. At a subsequent meeting with a number of
Advantage directors in early April, Wintrust's officers again expressed interest
in exploring a possible affiliation with Advantage and thereafter furnished a
written indication of interest, including a price proposal, to one of the
directors. Advantage's director responded to this indication of interest by
saying that he did not believe Advantage's board of directors would have any
interest at the initial price level expressed by Wintrust.

         Following further discussions between Wintrust and Advantage board
members, on April 9, 2003, Advantage's chairman of the board received a written
expression of interest proposing that Wintrust acquire 100% of Advantage's
common stock at an increased price of $26.50 per share, with the majority of the
consideration to be paid in Wintrust common stock. Advantage's executive
committee held several informal discussions about Wintrust's level of interest
and Advantage's prospects on a stand-alone basis.

         On April 11, 2003, Wintrust's chief executive officer met at
Advantage's Elk Grove office with three of Advantage's directors to discuss the
Wintrust philosophy, its commitment to community banking and the general
business terms of a possible stock-for-stock merger between Wintrust and
Advantage. On April 16, 2003, four of Advantage's directors (two of whom are
attorneys) and two of its executive officers met at Wintrust's headquarters with
its chief executive officer and its chief operating officer. They discussed
general business plans for both organizations and possible synergies resulting
from any affiliation. At this meeting, Advantage and Wintrust also signed an
exclusivity and mutual confidentiality agreement.


                                       20



         Following the April 16th meeting, Advantage's management engaged Barack
Ferrazzano Kirschbaum Perlman & Nagelberg LLC, as special counsel to Advantage,
to provide advice regarding a possible affiliation transaction with Wintrust. In
addition, Advantage's management provided to the directors who are not on the
executive committee preliminary information concerning the contacts with
Wintrust.

         Advantage's  board of  directors  met on April  22,  2003,  to  discuss
Wintrust's  indication of interest and the board's  long-term  strategic outlook
for Advantage.  A representative  of Barack  Ferrazzano was also present at this
meeting.  At the meeting,  senior executive  officers of Advantage  presented to
directors a  recently-completed  five-year  business  plan for Advantage and the
board compared the financial  aspects of Wintrust's  indication of interest with
the  likelihood  that Advantage  would be able to achieve the growth  objectives
indicated in the business plan.

         Based on the outcome of its deliberations at the meeting, the Board
directed members of its executive committee and management to continue
discussions with Wintrust in an effort to reach a final definitive proposal that
could be considered by the directors. Thereafter, both Wintrust and Advantage
commenced due diligence investigations of the other party.

         After the completion of the first phase of Wintrust's due diligence,
Advantage's executive committee and its special counsel met with representatives
of Wintrust and its counsel on May 16, 2003, to discuss the principal terms of a
proposed merger agreement that had been previously prepared and distributed by
Wintrust. After several hours of discussion, negotiations were halted due to the
parties' inability to agree on terms for the calculation of the exchange ratio.
Members of Advantage's executive committee held additional discussions about
this issue over the next few days with members of Wintrust's management.
Negotiations resumed the following week after the executive committee reached a
mutual understanding with Wintrust's officers regarding pricing and certain
limits placed on the maximum and minimum number of Wintrust shares of stock to
be issued in connection with the proposed merger.

         Over the ensuing weeks and with regular updates to their respective
boards, the parties, assisted by their respective legal advisers, continued due
diligence and negotiation of a definitive merger agreement.

         The Advantage board met on June 17, 2003 to consider the proposed
transaction and the terms of the proposed merger agreement, a draft and summary
of which had been provided to directors in advance. Also in attendance was a
representative of Barack Ferrazzano. Members of the board's executive committee
reviewed the process leading to the proposed transaction and described their
analysis of the proposed purchase price. The committee noted that it had
reviewed comparable sale transactions of other banks and concluded that the
price offered by Wintrust was at the upper end of this range, especially given
Advantage's relatively short business history. Based on these discussions and
review, the committee members said that they believed accepting the purchase
price offered by Wintrust was in the best interests of Advantage's shareholders.
In light of these conclusions, the board decided not to retain an outside
investment banking firm to issue a fairness opinion or pursue any alternative
strategic options. Following review and discussion at the meeting of the terms
of the transaction and the proposed merger agreement with management and legal
counsel, Advantage's board of directors approved the merger and authorized its
president to execute the merger agreement on behalf of Advantage.

         Advantage and Wintrust executed the merger agreement on July 2, 2003,
and issued a joint press release on the same date, announcing the execution of
the agreement.

WINTRUST'S REASONS FOR THE MERGER

         Wintrust's board of directors believes that the merger is in the best
interests of Wintrust and its shareholders. In deciding to approve the merger,
Wintrust's board of directors considered a number of factors, including:

         o        management's  view that the acquisition of Advantage  provides
                  an attractive opportunity to expand into the northwest Chicago
                  metropolitan area, which they consider a desirable market;


         o        the  community  banking   orientation  of  Advantage  and  the
                  compatibility of Advantage with Wintrust and its subsidiaries;



                                       21



         o        a  review  of  the   demographic,   economic   and   financial
                  characteristics  of the markets in which  Advantage  operates,
                  including  existing and potential  competition  and history of
                  the market areas with respect to financial institutions;

         o        management's review of the business, operations, earnings, and
                  financial  condition,   including  capital  levels  and  asset
                  quality, of Advantage since its de novo formation in 2001; and

         o        the  likelihood  of regulators  approving  the merger  without
                  undue conditions or delay.

         While Wintrust's board of directors considered these and other factors,
the board of directors did not assign any specific or relative weights to the
factors considered and did not make any determination with respect to any
individual factor. Wintrust's board of directors collectively made its
determination with respect to the merger based on the conclusion reached by its
members, based on the factors that each of them considered appropriate, that the
merger is in the best interests of Wintrust's shareholders. The terms of the
merger were the result of arm's-length negotiations between representatives of
Wintrust and representatives of Advantage.

ADVANTAGE'S REASONS FOR THE MERGER AND RECOMMENDATION OF THE BOARD OF DIRECTORS

         The Advantage board believes that the merger is fair to, and in the
best interests of, Advantage and its shareholders. Accordingly, the Advantage
board has unanimously approved the merger agreement and unanimously recommends
that its shareholders vote FOR the approval of the merger agreement and the
transactions it contemplates.

         Advantage's board has concluded that the proposed merger offers the
Advantage shareholders an opportunity to achieve the company's strategic
business objectives sooner than originally contemplated at the time that
Advantage formed Advantage National Bank in January 2001. These objectives
included increasing shareholder value, growing the size of the business and
enhancing liquidity for Advantage's shareholders, who will benefit by owning
shares of a publicly traded company.

         In deciding to approve the merger agreement and the transactions it
contemplates, Advantage's board consulted with Advantage's management, as well
as its legal counsel, and considered numerous factors, including the following:

         o        information with respect to the businesses, earnings,
                  operations, financial condition, prospects, capital levels and
                  asset quality of Advantage and Wintrust, both individually and
                  as a combined company;

         o        the market value of the Wintrust shares to be received by
                  Advantage shareholders, based upon the trading price of
                  Wintrust's common stock before the execution of the merger
                  agreement, that reflected a premium of more than 75% over the
                  $15.00 per share price paid by Advantage's shareholders during
                  2000 in connection with the organization of Advantage National
                  Bank;

         o        the perceived risks and uncertainties attendant to Advantage's
                  execution of its strategic growth plans as an independent
                  banking organization, including the need to access additional
                  capital and enhance its technology platform on a
                  cost-effective basis to support future growth;

         o        the belief that the market value of Wintrust's common stock
                  prior to the execution of the merger agreement was very
                  attractive and offered favorable prospects for future
                  appreciation as a result of the proposed merger and other
                  strategic initiatives being implemented by Wintrust;

         o        the strategic vision of the management of Wintrust to seek
                  profitable future expansion in the Chicago metropolitan area,
                  leading to continued growth in overall shareholder value;

         o        the fact that Wintrust is publicly held and the merger would
                  provide Advantage shareholders, whose investments currently
                  are in a privately held company, an ownership interest in a
                  publicly traded company, as well as enhanced access to capital
                  markets to finance the combined company's capital
                  requirements; and

         o        the likelihood that the merger will be approved by the
                  relevant bank regulatory authorities.


                                       22



         The above discussion of the information and factors considered by the
Advantage board is not intended to be exhaustive, but includes all material
factors considered by the Advantage board in arriving at its determination to
approve, and to recommend that the Advantage shareholders vote to approve, the
merger agreement and related transactions. The Advantage board did not assign
any relative or specific weights to the above factors, and individual directors
may have given differing weights to different factors. The Advantage board
unanimously recommends that its shareholders vote to approve the merger
agreement and the related transactions.

ACCOUNTING TREATMENT

         Wintrust will account for the merger under the "purchase" method of
accounting in accordance with accounting principles generally accepted in the
United States. Using the purchase method of accounting, the assets and
liabilities of Advantage will be recorded by Wintrust at their respective fair
values at the time of the completion of the merger. The excess of Wintrust's
purchase price over the net fair value of the assets acquired and liabilities
assumed will then be allocated to identified intangible assets, with any
remaining unallocated cost recorded as goodwill.

TAX CONSEQUENCES OF THE MERGER

         General. The following discussion addresses the material United States
federal income tax consequences of the merger that are generally applicable to
Advantage shareholders. It does not address the tax consequences of the merger
under foreign, state, or local tax laws or the tax consequences of transactions
completed before or after the merger. Also, the following discussion does not
deal with all federal income tax considerations that may be relevant to certain
Advantage shareholders in light of their particular circumstances, such as
shareholders who:

         o        are dealers in securities;

         o        are insurance companies or tax-exempt organizations;

         o        are subject to alternative minimum tax;

         o        hold their shares as part of a hedge, straddle, or other risk
                  reduction transaction; or

         o        are foreign persons.

         YOU ARE URGED TO CONSULT YOUR OWN TAX ADVISORS REGARDING THE TAX
CONSEQUENCES OF THE MERGER TO YOU BASED ON YOUR OWN CIRCUMSTANCES, INCLUDING THE
APPLICABLE FEDERAL, STATE, LOCAL, AND FOREIGN TAX CONSEQUENCES.

         The following discussion is based on the advice of Barack Ferrazzano
regarding the Internal Revenue Code of 1986, as amended, or the Code, applicable
Treasury Regulations, judicial decisions, and administrative rulings and
practice, all as of the date of this document and all of which are subject to
change. Any change could be applied to transactions that were completed before
the change, and could affect the accuracy of the statements and conclusions in
this discussion and the tax consequences of the merger to Wintrust, Advantage
and the Advantage shareholders.

         Tax Opinion of Barack Ferrazzano. Neither Wintrust nor Advantage has
requested, nor will they request, a ruling from the Internal Revenue Service
with regard to the federal tax consequences of the merger. Instead, as a
condition to the closing of the merger, Barack Ferrazzano, special legal counsel
to Advantage, will render its opinion to Advantage, subject to customary
representations and assumptions referred to in the opinion, substantially to the
effect that the merger will constitute a reorganization within the meaning of
Section 368(a) of the Code and Advantage and Wintrust will each be a "party to a
reorganization" within the meaning of Section 368(b) of the Code.

         Barack Ferrazzano's opinion will be based upon the assumption that the
merger will take place in the manner described in the merger agreement and will
qualify as a statutory merger under state law, and will also assume the truth
and accuracy of certain factual representations that have been made by Wintrust
and Advantage and which are customarily given in transactions of this nature.
Barack Ferrazzano's opinion is not binding on the Internal Revenue Service or
the courts and there can be no assurance that the Internal Revenue Service will
not take


                                       23



a  contrary  position  to one or more  positions  reflected  herein  or that the
opinion  will be upheld by the  courts if  challenged  by the  Internal  Revenue
Service.

         Provided that the merger constitutes a reorganization within the
meaning of Section 368(a) of the Code, Barack Ferrazzano has advised that for
federal income tax purposes:

         o        no gain or loss will be recognized by Wintrust or Advantage as
                  a result of the transactions contemplated in the merger;



         o        no income, gain or loss will be recognized by Advantage
                  shareholders upon the receipt of Wintrust common stock in
                  exchange for Advantage common stock, except with respect to
                  cash received for a fractional share of Wintrust common stock;

         o        the basis of the Wintrust common stock received by Advantage
                  shareholders in the merger will be the same as the basis of
                  the Advantage common stock surrendered, decreased by the
                  amount of any cash received and increased by the amount of any
                  gain recognized in the exchange;

         o        the holding period of the Wintrust common stock received by
                  Advantage shareholders will include the holding period of the
                  Advantage common stock surrendered, provided that the
                  Advantage common stock was held as a capital asset in the
                  hands of the Advantage shareholders on the date of the
                  exchange;

         o        the basis of the Advantage assets in the hands of Wintrust
                  will be the same as the basis of such assets in the hands of
                  Advantage immediately prior to the exchange; and

         o        the holding period of the Advantage assets transferred to
                  Wintrust will include the period during which such assets were
                  held by Advantage prior to the exchange.

         In general, holders of warrants to purchase Advantage common stock who
exchange those warrants for cash will recognize gain for federal income tax
purposes equal to the difference between the amount of cash received and their
basis in the warrants.

         Withholding. Cash payments in respect of a fractional share of Wintrust
common stock may be subject to the information reporting requirements of the
Internal Revenue Service and to backup withholding at the current rate of 28%.
Backup withholding will not apply to a payment made to you if you complete and
sign the substitute Form W-9 that will be included as part of the transmittal
letter and notice from Wintrust's exchange agent, or you otherwise prove to
Wintrust and its exchange agent that you are exempt from backup withholding.

         Backup withholding is not an additional tax, but an advance payment.
Any amount withheld from the payment of the merger consideration may be credited
against the United States federal income tax liability of the beneficial owner
subject to the withholding and may be refunded to the extent it results in an
overpayment of tax. You should consult with your tax advisor as to your
qualification for exemption from backup withholding and the procedures for
obtaining this exemption.

         Reporting and Record Keeping. If you exchange shares of Advantage
common stock in the merger for Wintrust common stock, you are required to retain
records of the transaction, and to attach to your federal income tax return for
the year of the merger a statement setting forth all relevant facts with respect
to the nonrecognition of gain or loss upon the exchange. At a minimum, the
statement must include:

         o        your tax basis in the Advantage common stock surrendered; and

         o        the amount of cash (if any) received and the fair market
                  value, as of the effective date of the merger, of the Wintrust
                  common stock received in exchange therefor.

         THE PRECEDING DISCUSSION DOES NOT PURPORT TO BE A COMPLETE ANALYSIS OF
ALL POTENTIAL TAX CONSEQUENCES OF THE MERGER THAT MAY BE RELEVANT TO A
PARTICULAR ADVANTAGE SHAREHOLDER. YOU ARE URGED TO CONSULT WITH YOUR OWN TAX
ADVISOR REGARDING THE SPECIFIC TAX CONSEQUENCES TO YOU AS A RESULT OF THE
MERGER, INCLUDING THE APPLICABILITY AND EFFECT OF FOREIGN, STATE, LOCAL AND
OTHER TAX LAWS.


                                       24


REGULATORY APPROVALS


         The merger of Wintrust and Advantage is subject to prior approval of
the Board of Governors of the Federal Reserve System, commonly known as the
Federal Reserve. Wintrust has submitted a notice filing with the Federal Reserve
Bank of Chicago seeking the necessary approval. Although there can be no
assurance that the Federal Reserve will approve the merger or as to timing of
approval, Wintrust currently expects that it will receive approval of the merger
during the fourth quarter of 2003. The merger may not be consummated until 15
days after receipt of Federal Reserve approval, during which time the United
States Department of Justice may challenge the merger on antitrust grounds. The
commencement of an antitrust action would stay the effectiveness of the Federal
Reserve's approval, unless a court specifically orders otherwise.

         The merger cannot proceed without obtaining all requisite regulatory
approvals. Wintrust has agreed to take all appropriate actions necessary to
obtain the required approvals. However, Wintrust is not obligated to accept any
terms or conditions in approvals that are objectionable to Wintrust.


INTERESTS OF CERTAIN PERSONS IN THE MERGER


         As of August 22, 2003, directors and officers of Advantage
beneficially owned, in the aggregate, 269,026 shares of Advantage common stock,
representing approximately 37% of the outstanding shares of Advantage common
stock. None of Wintrust or its directors, officers or affiliates holds any
shares of Advantage common stock.

         Employment Agreements. Advantage National Bank entered into employment
agreements with two of its executive officers, Mark Stetson and Paul Katauskas,
in June 2003. Gerhardt E. Umlauf, President and Chief Executive Officer of
Advantage National Bank, has had an employment agreement with Advantage since
2000. Under the merger agreement, at least one of these persons must be an
employee in good standing with Advantage or Advantage National Bank at closing,
and the employment agreements will continue in effect post closing.

         Each of Mr. Stetson's and Mr. Katauskas' employment agreements are for
a term of three years, and the term is renewable thereafter for additional one
year terms each year on the anniversary date of the agreement. Either party may
terminate the agreement with written notice to the other party at least 90 days
prior to the anniversary date of the agreement. The employment agreements
contain confidentiality agreements and one-year non-compete and non-solicitation
provisions in the event of termination of employment, and provide for one year
of severance pay equal to annual base salary in the event the executive is
terminated without cause. The agreements provide for an annual base salary of
$115,000 for Mr. Stetson and $100,000 for Mr. Katauskas. The executives may
receive annual discretionary bonuses and salary increases, are entitled to
participate in any employee insurance and fringe benefit programs of the bank,
and are entitled to certain perquisites under the agreements, including the use
of a company car.

         Mr. Stetson and Mr. Katauskas were granted options to purchase 10,000
and 7,225 shares, respectively, of Advantage common stock in connection with
entering into their agreements. These options are subject to a vesting schedule
whereby 25% of the shares subject to the option award vest on July 1, 2003 and
every January 1st thereafter through 2006. Under the merger agreement, the
options will be converted into options to purchase Wintrust common stock, and in
the event a change of control occurs after March 1, 2004, all of these options
will become immediately vested.


         Continued Director and Officer Liability Coverage. Pursuant to the
terms of the merger agreement, Wintrust will provide to each of the directors
and officers of Advantage and Advantage National Bank following the effective
time coverage against personal liability for actions taken after the effective
time of the merger that is substantially similar to the coverage Wintrust
provides to its current directors and officers. For a period of five years after
the effective time, Wintrust has agreed to indemnify and hold harmless the
current and former directors and officers of Advantage and Advantage National
Bank for all actions taken by them prior to the effective time of the merger, to
the same extent as Advantage and Advantage National Bank currently provide for
indemnification of their officers and directors.


                                       25



VOTING AGREEMENTS

         Each of the officers and directors of Advantage and Advantage National
Bank have entered into voting agreements with Wintrust. Under these agreements,
these shareholders have each agreed to vote their respective shares of Advantage
common stock:

         o        in favor of the merger and the transactions contemplated by
                  the merger agreement;


         o        against any action or agreement which would result in a
                  material breach of term of or any other obligation of
                  Advantage under the merger agreement; and

         o        against any action or agreement which would impede, interfere
                  with or attempt to discourage the transactions contemplated by
                  the merger agreement.


         Furthermore, each of these shareholders has also agreed not to grant
any proxies, deposit any shares of Advantage common stock into a voting trust or
enter into a voting agreement with respect to any Advantage common stock or
solicit, initiate or encourage any inquiries or proposals for a merger or other
business combination involving Advantage without Wintrust's prior approval. The
shares subject to the voting agreements represent approximately 37% of the
outstanding shares of Advantage common stock on the record date. Each
shareholder voting agreement will terminate upon the earlier of the consummation
of the merger or termination of the merger agreement in accordance with its
terms.


RESTRICTIONS ON RESALE OF WINTRUST COMMON STOCK

         This proxy statement/prospectus does not cover any resales of the
shares of Wintrust common stock to be received by Advantage's shareholders upon
completion of the merger, and no person may use this proxy statement/prospectus
in connection with any resale.

         All shares of Wintrust common stock issued to shareholders of Advantage
in connection with the merger will be freely transferable, except that shares
received by persons deemed to be "affiliates" of Advantage under the Securities
Act at the time of the Special Meeting may be resold only in transactions
permitted by Rule 145 under the Securities Act or otherwise permitted under the
Securities Act. Based on the number of shares of Wintrust common stock
anticipated to be received in the merger, it is expected that Rule 145 will not
limit the amount of shares that former Advantage shareholders will be able to
sell into the market. Persons who may be deemed affiliates of Advantage for this
purpose generally include directors, executive officers, and the holders of 10%
or more of the outstanding shares of Advantage common stock.

                       DESCRIPTION OF THE MERGER AGREEMENT

         The following summary of the merger agreement is qualified by reference
to the complete text of the merger agreement. A copy of the merger agreement is
attached as Annex A to this proxy statement/prospectus and is incorporated by
reference into this proxy statement/prospectus. You should read the merger
agreement completely and carefully as it, rather than this description, is the
legal document that governs the merger.

TIME OF COMPLETION

         The completion of the merger will take place on the fifth business day
after the day on which the last of the conditions to closing set forth in the
merger agreement have been fulfilled or waived or at another time that both
parties mutually agree upon. The completion of the merger sometimes is referred
to in this proxy statement/prospectus as the closing date. The time at which the
merger becomes effective is sometimes referred to in this proxy
statement/prospectus as the "effective time."


                                       26



CONSIDERATION TO BE RECEIVED IN THE MERGER

         Each share of Advantage common stock outstanding immediately before the
effective  time will,  at the  effective  time,  be converted  into the right to
receive the number of shares of Wintrust common stock equal to $26.50 divided by
the average  price of Wintrust  common  stock  during the pricing  period.  This
number is referred  to as the  "exchange  ratio." The pricing  period is the ten
consecutive trading days ending two trading days before, but not including,  the
closing date,  and the average price of Wintrust  common stock is defined as the
unweighted  average  high and low sales  prices of Wintrust  common stock on the
Nasdaq National Market during this period. If Wintrust or Advantage,  before the
effective  time,  changes  the number of shares of its common  stock  issued and
outstanding  through a stock split, stock  combination,  stock dividend or other
distribution, the cash and stock consideration will be appropriately adjusted to
reflect the split, combination,  dividend or distribution. The exchange ratio is
subject to possible adjustment as described in the following paragraph.

         If the average price of Wintrust common stock during the 10-day pricing
period before closing of the merger is less than $25.00 per share,  the exchange
ratio will be $26.50 divided by $25.00 for purposes of determining the number of
shares of Wintrust common stock to be issued to each Advantage  shareholder.  If
the average price of Wintrust  common stock during this 10-day pricing period is
greater  than $35.00 per share,  the  exchange  ratio will be $26.50  divided by
$35.00 for purposes of determining the number of shares of Wintrust common stock
to be issued to each Advantage shareholder.

         The  following  table  illustrates  the per  share  consideration  that
Advantage  shareholders  will receive in the merger based on a range of Wintrust
common stock prices.

                                                   PER SHARE VALUE OF
    WINTRUST AVERAGE            EXCHANGE            ADVANTAGE STOCK
      STOCK PRICE                RATIO               AT CLOSING(1)
      -----------                -----               -------------

         $ 40.00                 0.757                  $ 30.28
           39.00                 0.757                    29.52
           38.00                 0.757                    28.77
           37.00                 0.757                    28.10
           36.00                 0.757                    27.25
           35.00                 0.757                    26.50
           34.00                 0.779                    26.50
           33.00                 0.803                    26.50
           32.00                 0.828                    26.50
           31.00                 0.855                    26.50
           30.00                 0.883                    26.50
           29.00                 0.914                    26.50
           28.00                 0.946                    26.50
           27.00                 0.981                    26.50
           26.00                 1.019                    26.50
           25.00                 1.060                    26.50
           24.00                 1.060                    25.44
           23.00                 1.060                    24.38
           22.00                 1.060                    23.32
           21.00                 1.060                    22.26
           20.00                 1.060                    21.20

--------------
(1)     Assumes the closing price of Wintrust common stock on the date of the
        merger is the same as the average price during the pricing period. The
        actual trading price of Wintrust common stock is subject to market
        fluctuations, and Advantage shareholders will not be entitled to receive
        additional shares in the merger if the trading price of Wintrust common
        stock on the closing date of the merger is less than the average price
        during the pricing period.

         Instead of issuing a fractional share of Wintrust common stock in
connection with payment of the stock consideration, cash will be paid in an
amount determined by multiplying the fractional share by the average price
during the pricing period.

                                       27



         Warrants and Stock Options. Each warrant to purchase Advantage common
stock outstanding at the effective time of the merger will be converted into the
right to receive an amount in cash equal to the number of shares of Advantage
common stock subject to the warrant multiplied by the difference between (i)
$26.50 and (ii) the per share exercise price associated with that warrant.
Options to purchase Advantage common stock that are outstanding and unexercised
immediately before the effective time of the merger will be converted into the
right to receive options to purchase Wintrust common stock. The number of shares
of Wintrust common stock subject to the converted stock option will be equal to
the number of shares of Advantage common stock subject to the Advantage stock
option multiplied by the exchange ratio. The exercise price of the converted
stock option will equal the Advantage stock option's exercise price divided by
the exchange ratio. Except as described above, the converted stock options will
have the same terms and conditions as the Advantage stock options. All
outstanding Advantage stock options, subject to limited exceptions, will become
vested and immediately exercisable at the effective time of the merger.

EXCHANGE OF CERTIFICATES

         Wintrust has engaged Illinois Stock Transfer Company to act as its
exchange agent to handle the exchange of Advantage common stock for the merger
consideration and the payment of cash for any fractional share interest. Within
five days of the effective time, the exchange agent will send to each Advantage
shareholder a letter of transmittal for use in the exchange with instructions
explaining how to surrender Advantage common stock certificates to the exchange
agent. Advantage shareholders that surrender their certificates to the exchange
agent, together with a properly completed letter of transmittal, will receive
the merger consideration. Advantage shareholders that do not exchange their
Advantage common stock will not be entitled to receive any dividends or other
distributions by Wintrust until their certificates are surrendered. After
surrender of the certificates representing Advantage shares, any unpaid
dividends or distributions with respect to the Wintrust common stock represented
by the certificates will be paid.

CONDUCT OF BUSINESS PENDING THE MERGER AND CERTAIN COVENANTS

         Under the merger agreement, Advantage has agreed to certain
restrictions on its activities until the merger is completed or terminated. In
general, Advantage and its subsidiaries are required to conduct their business
in the ordinary course of business, consistent with prudent banking practice.

         The following is a summary of the more significant restrictions imposed
upon Advantage, subject to the exceptions set forth in the merger agreement:

         o        issuing, selling, purchasing or redeeming its securities;

         o        paying any dividends or other distributions;

         o        amending its articles of incorporation or by-laws;

         o        increasing compensation or benefits for officers or key
                  employees or paying any bonuses;

         o        making any expenditure for fixed assets in excess of $25,000
                  for any single item, or $100,000 in the aggregate;

         o        making or becoming party to a contract, commitment, or
                  transaction, other than in the ordinary course of business
                  consistent with prudent banking practice and Advantage's
                  policies;

         o        making any loan in excess of $500,000 other than in the
                  ordinary course of business consistent with prudent banking
                  practice;

         o        entering into employment, consulting, or similar agreements
                  that cannot be terminated with less than 30 days notice
                  without penalty;

         o        buying or investing in government securities that have
                  maturities of more than five years and a rating agency rating
                  below "A"; and


                                       28



         o        changing in any material respect any accounting, banking, or
                  investment policies.

         Wintrust has agreed to file all applications and notices to obtain the
necessary regulatory approvals for the transactions contemplated by the merger
agreement. Advantage has agreed to cooperate with Wintrust in connection with
obtaining the regulatory approvals. Both parties agree:

         o        to use all reasonable efforts and to cooperate in the
                  preparation and filing of all applications, notices and
                  documents required to obtain regulatory approval and/or
                  consents from governmental authorities for the merger and the
                  merger agreement;

         o        to use reasonable and diligent good faith efforts to satisfy
                  the conditions required to close the merger and to consummate
                  the merger as soon as practicable;

         o        that neither will intentionally act in a manner that would
                  cause a breach of the merger agreement or that would cause a
                  representation made in the merger agreement to become untrue;

         o        to provide the other party with reasonable access to
                  information under the condition that the information be kept
                  confidential; and

         o        to coordinate publicity of the transactions contemplated by
                  the merger agreement with the media and Advantage
                  shareholders.

         Advantage has agreed that it will not encourage any third-party
proposals to acquire Advantage and will not participate in negotiations
regarding a proposal to acquire Advantage. However, Advantage may provide
information and negotiate with a third party if the Advantage Board of Directors
determines that failure to do so would be inconsistent with their fiduciary
duties. Advantage is required under the agreement to provide Wintrust notice of
any proposal to acquire Advantage.

         Advantage has also agreed to provide Wintrust with certain documents
before the closing date, including:

         o        interim financial statements;

         o        prompt notice of any exercise of dissenters' rights;

         o        reasonable notice of any Advantage board and committee
                  meetings; and

         o        loan information.

         The merger agreement also contains certain covenants relating to
employee benefits and other matters pertaining to officers and directors. See
"Description of the Merger -- Employee Benefit Matters" and "Description of the
Merger -- Interests of Certain Persons in the Merger."

REPRESENTATIONS AND WARRANTIES

         The merger agreement contains representations and warranties made by
Advantage and Wintrust. These include, among other things, representations
relating to:

         o        valid corporate organization and existence;

         o        corporate power and authority to enter into the merger and the
                  merger agreement;

         o        capitalization;

         o        financial statements;

         o        tax matters;

         o        environmental matters;



                                       29



         o        absence of material adverse changes;

         o        government approvals required in connection with the merger;

         o        compliance with material contracts;

         o        absence of undisclosed investigations and litigation;

         o        compliance with laws;

         o        investment banker/finder fees;

         o        governmental registrations, licenses, permits, and reports;

         o        absence of default under any material contract;

         o        absence of material omissions; and

         o        absence of any breach of organizational documents, law or
                  other agreements as a result of the merger.

         Wintrust and Wintrust Merger Co. also represent and warrant to
Advantage in the merger agreement regarding:

         o        compliance with SEC filing requirements;

         o        compliance with ERISA; and

         o        administration of fiduciary accounts.

         Advantage makes additional representations and warranties to Wintrust
in the merger agreement relating to, among other things:

         o        organizational documents and stock records;

         o        title to real property, personal property, and other material
                  assets;

         o        insurance matters;

         o        employee benefits;

         o        ownership of subsidiaries;

         o        material contracts;

         o        loans;

         o        investment securities;

         o        compliance with the Community Reinvestment Act;

         o        conduct of business and maintenance of business relationships;

         o        technology and intellectual property;

         o        absence of undisclosed liabilities;

         o        reserve for loan and lease losses; and

         o        affiliate transactions.


                                       30



CONDITIONS TO COMPLETION OF THE MERGER

         Closing Conditions for the Benefit of Wintrust. Wintrust's obligations
are subject to fulfillment of the following conditions:

         o        the accuracy of representations and warranties of Advantage in
                  all material respects as of the effective time;

         o        performance by Advantage in all material respects of its
                  agreements under the merger agreement;

         o        the registration statement has been declared effective by the
                  SEC and continues to be effective as of the effective time;

         o        approval of the merger by Advantage shareholders;

         o        receipt of all necessary regulatory approvals;

         o        no adverse material change in Advantage since July 2, 2003;

         o        no litigation resulting from the transactions contemplated by
                  the merger agreement;

         o        receipt of certain certificates and a legal opinion from
                  Advantage;

         o        receipt of voting agreements;

         o        receipt of environmental surveys;

         o        continued employment of certain Advantage employees;

         o        maintenance of minimum net worth and loan loss reserve
                  requirements; and

         o        receipt of necessary consents/waivers and opinions.

         Closing Conditions for the Benefit of Advantage. Advantage's
obligations are subject to fulfillment of the following conditions:

         o        accuracy of representations and warranties of Wintrust and
                  Wintrust Merger Co. in all material respects as of the
                  effective time

         o        performance by Wintrust and Wintrust Merger Co. in all
                  material respects of their agreements under the merger
                  agreement;

         o        Wintrust's common stock, when issued as merger consideration,
                  shall be included for trading on Nasdaq;

         o        receipt of all necessary regulatory approvals;

         o        execution and delivery of the merger agreement and articles of
                  merger suitable for filing with the Illinois Secretary of
                  State;

         o        the registration statement has been declared effective by the
                  SEC and continues to be effective as of the effective time;

         o        no litigation resulting from the transactions contemplated by
                  the merger agreement;

         o        no material adverse change in Wintrust since July 2, 2003; and

         o        receipt of certain certificates and opinions.

                                       31


TERMINATION

         The merger agreement may be terminated under any of the following
circumstances, as set forth in the merger agreement:

         o        at any time by written agreement of Wintrust and Advantage;

         o        by either party if:

                  o        the effective time has not occurred by December 31,
                           2003 or such later date agreed to by the parties;
                           provided, that the termination date will be extended
                           to March 31, 2004 if the sole impediment to closing
                           is due to delays in receiving regulatory approval
                           from the SEC or the Federal Reserve;

                  o        the other party has not satisfied any of the closing
                           conditions set forth in the merger agreement; or

                  o        Advantage receives and accepts a superior proposal
                           for acquisition by a third party.

         o        by Wintrust if Advantage has not satisfied a condition under
                  the merger agreement required to be met by Advantage prior to
                  the closing date, or if it becomes impossible for Advantage to
                  satisfy a condition and Advantage's inability to satisfy the
                  condition was not caused by Wintrust's failure to meet any of
                  its obligations under the Agreement;

         o        by Advantage if Wintrust has not satisfied a condition under
                  the merger agreement required to be met by Wintrust prior to
                  the closing date, or if it becomes impossible for Wintrust to
                  satisfy a condition and Wintrust's inability to satisfy the
                  condition was not caused by Advantage's failure to meet any of
                  its obligations under the Agreement;

TERMINATION FEE

         Wintrust may demand a $1,000,000 termination fee from Advantage if the
merger agreement is terminated under the following circumstances:

         o        Advantage solicits or facilitates an acquisition proposal by a
                  third party, or receives and accepts a superior proposal for
                  acquisition by a third party;

         o        If, within six months following a termination of the
                  agreement, Advantage consummates or enters into a transaction
                  that would result in a change of control of Advantage or
                  Advantage National Bank pursuant to the terms of a proposal
                  known to Advantage before the termination of the agreement,
                  but which was not disclosed to Wintrust.




MANAGEMENT AND OPERATIONS AFTER THE MERGER


         After the merger, the Wintrust board of directors will remain the same;
the Advantage board of directors will likely change to include certain members
of Wintrust's management.


EMPLOYEE BENEFIT MATTERS

         The merger agreement calls for Wintrust to assume and continue most of
Advantage's employee benefit plans and arrangements, but Wintrust reserves the
right to amend or terminate these plans and arrangements in accordance with the
terms of the plans and arrangements and applicable laws. If Wintrust chooses to
terminate any Advantage plan after the closing date, employees previously
covered under the terminated plan will be eligible to participate in a similar
Wintrust benefit plan.

EXPENSES

         All expenses incurred in connection with the merger agreement will be
paid by the party incurring the expenses, except that the fees paid in
connection with the filing and distribution of the registration statement will
be

                                       32


shared equally between Advantage and Wintrust. Wintrust and Advantage have
also agreed to pay each other certain expenses not exceeding $150,000 in the
event the merger is terminated prior to the closing date for certain specified
reasons relating to a material breach of the merger agreement.

NASDAQ STOCK LISTING

         Wintrust common stock currently is listed on the Nasdaq National Market
under the symbol "WTFC." The shares to be issued to the Advantage shareholders
as merger consideration also will be eligible for trading on the Nasdaq National
Market.

                        COMPARISON OF SHAREHOLDER RIGHTS


         The rights of shareholders of Advantage, an Illinois corporation, are
governed by Advantage's articles of incorporation and by-laws as well as the
Illinois Business Corporation Act (the "IBCA"). Upon completion of the merger,
the rights of Advantage shareholders who receive shares of Wintrust common stock
in exchange for their shares of Advantage common stock and become shareholders
of Wintrust will be governed by the articles of incorporation and by-laws of
Wintrust. Wintrust is also an Illinois corporation governed by the IBCA, as well
as the rules and regulations applying to public companies. The following
discussion summarizes material differences between the rights of Advantage and
Wintrust shareholders and is not a complete description of all the differences.
This discussion is qualified in its entirety by reference to the IBCA and
Wintrust's and Advantage's articles of incorporation and by-laws.


AUTHORIZED CAPITAL STOCK


         The authorized capital stock of Advantage consists of 100,000 shares of
preferred stock, par value $5.00 per share, and 3 million shares of common
stock, par value $5.00 per share. Wintrust is authorized to issue 20 million
shares, without par value, of preferred stock, and 30 million shares, without
par value, of common stock. At August 29, 2003, Wintrust had 17,472,036 shares
of common stock outstanding. No shares of preferred stock have been issued.
Issuance of shares of Wintrust's preferred stock would affect the relative
rights of the holders of its common stock, depending upon the exact terms,
qualifications, limitations and relative rights and preferences, if any, of the
shares of the preferred stock as determined by the Board of Directors.


PAYMENT OF DIVIDENDS

         The IBCA governs the ability of Advantage and Wintrust to pay
dividends. As an Illinois corporation, no dividends or other distributions may
be paid to shareholders if the distribution would have the effect of making the
corporation insolvent or if, after payment of the dividend, the net assets of
the corporation would be less than zero or less than the maximum amount payable
at the time of distribution to shareholders having preferential rights in the
liquidation of the corporation if it were to be liquidated.


         Wintrust may pay dividends if, as and when declared by its Board of
Directors. As noted above, Wintrust's ability to pay dividends is subject to
limitations imposed by the IBCA. If Wintrust issues any shares of its preferred
stock in the future, the holders of its preferred stock may have a priority over
the holders of its common stock with respect to dividends.


ADVANCE NOTICE REQUIREMENTS FOR PRESENTATION OF BUSINESS AND NOMINATIONS OF
DIRECTORS AT ANNUAL MEETINGS OF SHAREHOLDERS


         Wintrust's by-laws provide that nominations for the election of
directors may be made by its board of directors or by any shareholder entitled
to vote for the election of directors, subject to the nomination having been
made in compliance with certain notice and informational requirements.
Wintrust's by-laws provide that Wintrust must receive written notice of any
shareholder director nomination or proposal for business at an annual meeting of
shareholders no later than 60 days before the date of the mailing of the proxy
materials. If, however, the date of the meeting has changed more than 30 days
from the anniversary date of the prior year annual meeting, the notice must be
delivered to Wintrust no later than 90 days before the meeting. Approval of any
shareholder proposals or director nominations requires a super majority vote of
85% of the outstanding shares. Wintrust shareholders do not have the right to
propose business for action at special meetings of shareholders.


                                       33


         Under Advantage's by-laws and articles of incorporation, there are no
advance notice requirements or other restrictions on the presentation of
business or the nomination or election of directors at shareholder meetings.


QUORUM


         Advantage's by-laws provide that a majority of the outstanding shares
of the corporation entitled to vote on a matter, in person or by proxy,
constitutes a quorum for the taking of action at a meeting of shareholders.
Wintrust's by-laws contain essentially the same provision.  Like Advantage
shareholders, each Wintrust shareholder is entitled to one vote for each share
owned.

ELECTION, CLASSIFICATION AND SIZE OF BOARD OF DIRECTORS

         Under Advantage's articles of incorporation and by-laws, its board of
directors is divided into three classes with one class elected for a three-year
term at each annual meeting of shareholders. The articles and by-laws provide
that the number of directors shall be not less than 10 or more than 20. The
number currently designated by Advantage is 12.

         Similarly, Wintrust's board of directors is divided into three classes.
Each class serves a staggered term, with one class or approximately one-third of
the total number of directors being elected for a three-year term at each annual
meeting of shareholders. Wintrust's by-laws state that the number of directors
shall be 14; however, the Board of Directors may increase or decrease that
number so long as there are not less than six directors at any time. The number
of directors currently designated by Wintrust is 14. Shareholders do not have
any right to cumulate votes in the election of directors. The staggered election
of directors ensures that at any given time, approximately two-thirds of the
directors serving will have had prior experience on the board. Staggered terms
for directors also moderate the pace of any change in the board by extending the
time required to elect a majority of directors from one to two years. It would
be impossible, assuming no resignations or removals of directors, for Wintrust's
shareholders to change a majority of the directors at any annual meeting should
they consider such a change desirable, unless this provision of Wintrust's
articles of incorporation is amended by action of at least 85% of Wintrust's
voting shares.


REMOVAL OF DIRECTORS

         As permitted under the IBCA, Advantage's articles of incorporation
provide that a director may be removed only for cause, at a meeting of
shareholders, by the affirmative vote of the holders of a majority of
outstanding shares entitled to vote. Under the IBCA, the notice of the meeting
must state that a purpose of the meeting is to vote on the removal of the
director named in the notice.

         Wintrust's directors may be removed by shareholders with or without
cause, at a duly called meeting of shareholders by the affirmative vote of the
holders of a majority of outstanding shares entitled to vote.

FILLING VACANCIES ON THE BOARD OF DIRECTORS


         Wintrust's by-laws provide that any vacancies and newly created
directorships on the board of directors shall be filled for the remainder of the
unexpired term exclusively by a majority vote of the directors then in office.
Shareholders do not have the right to fill vacancies.


         Advantage's articles of incorporation and by-laws provide that any
vacancies on the Board of Directors may be filled by the vote of 75% of the
directors then in office or by shareholder action. Any appointed directors will
serve until the next shareholder meeting electing the class for which such
directors have been chosen.

AMENDMENT OF ARTICLES OF INCORPORATION AND BY-LAWS

         Advantage's articles of incorporation may be amended by the affirmative
vote of a majority of the shares entitled to vote so long as at least 75% of the
number of directors then authorized to serve have first approved the proposed
amendment. Advantage's by-laws may be amended or repealed by a majority of
directors or shareholders.


         Any amendment of Wintrust's articles of incorporation must be approved
by a majority vote of the board of directors and also by a vote of at least
two-thirds of the outstanding shares of common stock. However, amendment


                                       34


of certain provisions of Wintrust's articles of incorporation requires a higher
vote of 85% or more of the outstanding shares. These include provisions relating
to: prohibiting cumulative voting rights; the prohibition of shareholder
action by written consent; indemnification; the number and classification of
directors; and amendment of certain sections of the articles of incorporation.
Wintrust's by-laws may be amended only by the board of directors.


MERGERS, ACQUISITIONS AND OTHER TRANSACTIONS

         Under the IBCA, unless a corporation's articles of incorporation
provide otherwise, approval by two-thirds of the voting power of the corporation
is required for mergers, consolidating other transactions involving any sale,
lease, exchange or disposition of all or substantially all of its assets or
dissolution. Advantage's articles of incorporation state that transactions
involving any sale, lease, exchange or disposition of all or substantially all
of its assets or dissolution requires the affirmative vote of the holders of at
least 75% of its outstanding common stock. However, if the transaction has been
approved by 75% or more of Advantage's directors, approval by only a majority of
shareholders is required.

         Wintrust's articles of incorporation do not specify a different
percentage than required by law, except as discussed below regarding business
combinations with certain persons. See "Business combinations with interested
shareholders."

BUSINESS COMBINATIONS WITH INTERESTED SHAREHOLDERS

         As a public company, Wintrust is governed by the provisions of Section
7.85 of the IBCA which applies to a transaction with an "Interested Shareholder"
(as defined below) (the "IBCA fair price provision"). Fair price provisions are
designed to impede two-step takeover transactions which might otherwise result
in disparate treatment of Wintrust's shareholders. Advantage is not governed by
Section 7.85.


         Under the IBCA fair price provision, the approval of at least 80%
percent of the shares is required in connection with any transaction involving
an Interested Shareholder except (i) in the cases where the proposed transaction
has been approved in advance by a majority of those members of the corporation's
board of directors who are unaffiliated with the Interested Shareholder and were
directors prior to the time when the Interested Shareholder became an Interested
Shareholder or (ii) if the proposed transaction meets certain conditions set
forth therein which are designed to afford the shareholders a fair price in
consideration for their shares, in which case approval of only a majority of the
outstanding shares of voting stock is required.


         The term "Interested Shareholder" is defined in the IBCA to include any
individual, corporation, partnership or other entity (other than the corporation
or any subsidiary) which owns beneficially or controls, directly or indirectly,
10% or more of the outstanding shares of the corporation's voting stock.

LIMITATIONS ON DIRECTORS' LIABILITY

         Wintrust's articles of incorporation provides that no director will be
personally liable to the corporation or any of its shareholders for monetary
damages for any breach of fiduciary duty except, as required by the IBCA, as
follows:

                  (1) for breach of duty of loyalty to the corporation or the
         shareholders;

                  (2) for acts and omissions not in good faith or which involved
         intentional misconduct or a knowing violation of law;

                  (3) for deriving an improper personal benefit from a
         transaction with the corporation; or

                  (4) under Section 8.65 of the IBCA, which creates liability
         for unlawful payment of dividends and unlawful stock purchases or
         redemptions.

         Similarly, Advantage's articles of incorporation provide that, to the
extent permitted under the IBCA, no director will be personally liable to the
corporation or any of its shareholders for monetary damages for any breach of
fiduciary duty.



                                       35


INDEMNIFICATION

         Under the IBCA, a corporation may indemnify its directors, officers,
employees and certain other individuals against expenses, including attorneys'
fees, judgments, fines and amounts paid in settlement in connection with
actions, suits or proceedings arising because of the person's relationship to
the corporation. The indemnification generally will cover expenses regardless of
whether it is a civil, criminal, administrative or investigative proceeding if
the individual acted in good faith and in a manner he or she reasonably believed
to be in, or not opposed to, the best interest of the corporation and, in the
case of a criminal proceeding, had no reasonable cause to believe his or her
conduct was unlawful. A similar standard applies in an action or suit by or in
the right of the corporation, but only extends to expenses, including attorneys'
fees, incurred in defense of the proceeding. In these cases, court approval is
required before there can be any indemnification when the person seeking
indemnification has been found liable to the corporation. To the extent a person
otherwise eligible for indemnification is successful on the merits or otherwise
in defense of any action, suit or proceeding described above, indemnification
for expenses, including attorneys' fees, actually and reasonably incurred is
required under the IBCA.

         Advantage's articles of incorporation and by-laws provide for the same
indemnification as the IBCA.

         Wintrust's articles of incorporation generally provides for the same
indemnification as the IBCA, including the advancement of expenses to the extent
permitted by law. Wintrust's articles of incorporation also provide for the
continuation of indemnification after the termination of the indemnified
person's association with Wintrust.

ACTION BY SHAREHOLDERS WITHOUT A MEETING

         Under the IBCA, unless the articles of incorporation provide otherwise,
shareholders may act by written consent if the consent is signed by shareholders
who collectively own the number of shares that would have been required to take
action at an actual shareholder meeting. Advantage's and Wintrust's articles of
incorporation provide that no action by written consent is permitted by
shareholders. All action required or permitted to be taken by shareholders must
be effected at a duly called annual or special meeting of Advantage or Wintrust
shareholders, as the case may be.

SPECIAL MEETINGS OF SHAREHOLDERS

         The IBCA provides that special meetings may be called by the president,
by the Board of Directors, by the holders of not less than one-fifth of all the
outstanding shares entitled to vote on the matter for which the meeting is
called, or by any other persons as the articles of incorporation or by-laws may
provide. Advantage's by-laws state that a special meeting may be called by the
persons named in the statute, while Wintrust's by-laws state that special
meetings only may be called by the chairman of the board of directors or the
president of Wintrust.

PREEMPTIVE RIGHTS


         Under the IBCA, preemptive rights will not be available unless a
corporation's articles of incorporation specifically provides for these rights.
Both Wintrust and Advantage's articles of incorporation do not provide for
preemptive rights.  Accordingly, Wintrust shareholders are not entitled to
preemptive rights with respect to any shares that Wintrust may issue in the
future.


APPRAISAL RIGHTS OF DISSENTING SHAREHOLDERS

         Under the IBCA, the rights of dissenting shareholders to obtain the
fair value for their shares may be available in connection with a merger or
consolidation in certain situations. Dissenters' rights are available to
Advantage shareholders in connection with the merger because the merger requires
shareholder approval. For a description of dissenters' rights, see "Special
Meeting of Advantage Shareholders -- Dissenters' Rights."


CERTAIN ANTI-TAKEOVER EFFECTS OF WINTRUST'S ARTICLES AND BY-LAWS AND ILLINOIS
LAW

         Certain provisions of Wintrust's articles of incorporation, by-laws and
the IBCA may have the effect of impeding the acquisition of control of Wintrust
by means of a tender offer, a proxy fight, open-market purchases or otherwise in
a transaction not approved by Wintrust's board of directors.


                                       36



         These provisions may have the effect of discouraging a future takeover
attempt which is not approved by Wintrust's board of directors but which
individual Wintrust shareholders may deem to be in their best interests or in
which Wintrust shareholders may receive a substantial premium for their shares
over then current market prices. As a result, shareholders who might desire to
participate in such a transaction may not have an opportunity to do so. Such
provisions will also render the removal of Wintrust's current board of directors
or management more difficult.

         These provisions of Wintrust's articles of incorporation and by-laws
include the following:

                  (1) Wintrust's board of directors may issue additional
         authorized shares of Wintrust's capital stock to deter future attempts
         to gain control of Wintrust, including the authority to determine the
         terms of any one or more series of preferred stock, such as voting
         rights, conversion rates, and liquidation preferences. As a result of
         the ability to fix voting rights for a series of preferred stock, the
         board has the power to the extent consistent with its fiduciary duty to
         issue a series of preferred stock to persons friendly to management in
         order to attempt to block a merger or other transaction by which a
         third party seeks control, and thereby assist the incumbent board of
         directors and management to retain their respective positions;

                  (2) Wintrust's staggered board is intended to provide for
         continuity of its board of directors and to make it more difficult and
         time consuming for a shareholder group to fully use its voting power to
         gain control of the board of directors without the consent of
         Wintrust's incumbent board of directors;

                  (3) Wintrust's articles of incorporation do not provide for
         cumulative voting for any purpose, and its articles and by-laws also
         provide that any action required or permitted to be taken by its
         shareholders may be taken only at an annual or special meeting and
         prohibits shareholder action by written consent in lieu of a meeting;

                  (4) Wintrust's articles of incorporation expressly elect to be
         governed by the provisions of Section 7.85 of the IBCA, as discussed
         above. Under the IBCA fair price provision and Wintrust's articles
         of incorporation, the approval of at least 80% of its shares is
         required in connection with any transaction involving an Interested
         Shareholder, subject to certain exceptions. Fair price provisions are
         designed to impede a two-step takeover transactions which might
         otherwise result in disparate treatment of Wintrust's shareholders; and

                  (5) Amendment of Wintrust's articles of incorporation must be
         approved by a majority vote of the board of directors and also by a
         two-thirds vote of the outstanding shares of Wintrust common stock,
         provided, however, that an affirmative vote of at least 85% of the
         outstanding voting stock entitled to vote is required to amend or
         repeal certain provisions of the articles of incorporation, including
         provisions (a) limiting voting rights, (b) relating to certain business
         combinations, (c) limiting the shareholders' ability to act by written
         consent, (d) regarding the number, classification of directors, filling
         of Board vacancies, newly created directorships, indemnification of
         directors and officers by Wintrust and limitation of liability for
         directors, and (e) regarding amendment of the foregoing super majority
         provisions of Wintrust's articles of incorporation. Wintrust's by-laws
         may be amended only by the board of directors.

         The provisions described above are intended to reduce Wintrust's
vulnerability to takeover attempts and certain other transactions which have not
been negotiated with and approved by members of its board of directors.


RIGHTS PLAN


         Wintrust has a shareholders rights plan which could discourage
unsolicited or hostile takeover attempts which are not negotiated with its board
of directors. The plan discourages such attempts by causing substantial dilution
to any person who acquires an amount in excess of a specified percentage of
Wintrust's common stock and by making an acquisition of Wintrust, without the
consent of its board of directors, prohibitively expensive. The description of
the rights plan set forth below does not purport to be complete and is qualified
in its entirety by reference the description of the rights plan set forth in
Wintrust's Registration Statement on Form 8-A dated August 28, 1998. See
"Incorporation of Certain Information by Reference" on page 42.



                                       37



         Each share of Wintrust common stock has attached to it a stock purchase
right having the terms set forth in a rights agreement between Wintrust and
Illinois Stock Transfer Company, as rights agent. Each right will entitle its
registered holder to purchase from Wintrust one one-hundredth of a share of
Junior Serial Preferred Stock A, without par value, at a price of $85.00 per one
one-hundredth share, subject to certain adjustments. Generally, the rights
become exercisable when any person or group (i) acquires or obtains the right to
acquire 15% or more of Wintrust's common stock, or (ii) commences (or announces
its intention to commence) a tender or exchange offer to acquire 15% or more of
Wintrust's common stock.

         In the event that any person or group becomes the beneficial owner of
15% or more of Wintrust's common stock, rights owned by that person or group
will immediately become null and void. Thereafter, other registered rights
holders will have the right to receive, upon exercise at the then current
exercise price of the right, Wintrust common stock having a value equal to two
times the exercise price of the right. Additionally, if, after any person or
group has acquired 15% or more Wintrust's common stock, Wintrust is acquired in
a merger or other business combination or 50% or more of Wintrust's assets or
earning power are sold, then each registered right holder will receive the right
to purchase, for the exercise price, common stock of the entity which acquires
or survives Wintrust having a value equal to twice the exercise price of the
right.

         Prior to any person or group acquiring 15% or more of Wintrust's common
stock, Wintrust may redeem the rights in whole, but not in part, at a price of
$0.01 per right to be paid in cash, shares of Wintrust common stock or other
consideration. In addition, at any time after a person or group acquires 15% of
Wintrust's common stock, but prior to such person or group acquiring 50% or more
of Wintrust's common stock, Wintrust may exchange the rights, in whole or in
part, at an exchange ratio of one share of common stock per right. The rights
will expire on July 31, 2008 unless exercised, redeemed, exchanged or otherwise
cancelled before that date.

         Advantage does not have a shareholder rights plan.


                              BUSINESS OF WINTRUST


         Financial and other information relating to Wintrust, including
information relating to Wintrust's current directors and executive officers, is
set forth in Wintrust's 2002 Annual Report on Form 10-K, Wintrust's Proxy
Statement for its 2003 Annual Meeting of Shareholders filed with the SEC on
April 29, 2003, Wintrust's 2003 Quarterly Reports on Form 10-Q and Wintrust's
Current Reports on Form 8-K filed during 2003, which are incorporated by
reference to this proxy statement/prospectus and copies of which may be obtained
from Wintrust as indicated under "Where You Can Find More Information" on
page 40. See "Incorporation of Certain Information by Reference" on page 41.

         Wintrust Financial Corporation, an Illinois corporation, is a financial
holding company headquartered in Lake Forest, Illinois. Wintrust currently
operates seven community banks, primarily in affluent suburbs of Chicago, which
provide community-oriented, personal and commercial banking services primarily
to individuals and small to mid-size businesses through 32 banking facilities.
Wintrust also provides trust, investment and asset management services through
its subsidiaries to customers of its banks. Through Wayne Hummer Investments,
LLC and Wayne Hummer Asset Management Company, Wintrust provides brokerage,
investment and asset management services to customers, primarily in the Midwest,
as well as to customers of its banks. Wintrust also provides trust and asset
management services through its subsidiary, Wayne Hummer Trust Company. In
addition, Wintrust is involved in specialty lending through operating
subsidiaries or divisions of certain of its banks. Its specialty lending niches
include one of the five largest, based on management's estimates, commercial
insurance premium finance companies in the United States; a company which
provides accounts receivable financing and administrative services to the
temporary staffing industry; and an indirect auto lending business which
purchases loans through Chicago-area automobile dealerships. As of June 30,
2003, Wintrust had consolidated total assets of $4.1 billion, deposits of $3.4
billion and shareholders' equity of $249.4 million.


RECENT DEVELOPMENTS

         On August 7, 2003, Wintrust announced the signing of a definitive
agreement to acquire Village Bancorp, Inc. ("Village") in a stock merger
transaction. Village is the parent company of Village Bank and Trust-Arlington
Heights ("Village Bank") that has locations in Arlington Heights and Prospect
Heights, Illinois. Village Bank began operations as a de novo bank in 1995 and
had total assets of approximately $74 million as of June 30, 2003.


                                       38




         In the proposed merger, each share of Village common stock outstanding
will be converted into the right to receive shares of Wintrust's common stock
based on Wintrust's average trading price at closing determined in accordance
with the merger agreement. At June 30, 2003, Village had outstanding 1,052,054
shares of common stock and in-the-money warrants to acquire approximately
150,000 shares of common stock at exercise prices ranging from $6.50 to $7.50
per share. Under the agreement, any warrants not exercised prior to the closing
date will be cashed out based on the resulting per share value. Depending on the
average price of Wintrust common stock at closing, Wintrust may issue up to
360,000 shares of its common stock in the merger. Consummation of the
transaction is not expected to have a material impact on Wintrust's 2003 or 2004
earnings per share.


         The transaction is subject to approval by regulators and Village's
shareholders and certain closing conditions. The transaction is expected to
close in the fourth quarter of 2003.


                              BUSINESS OF ADVANTAGE

         Advantage, an Illinois corporation, is a bank holding company
registered pursuant to the Bank Holding Company Act of 1956, as amended. As of
June 30, 2003, Advantage had consolidated total assets of $107.5 million,
deposits of $95.6 million and shareholders' equity of $9.4 million. Advantage
owns 100% of the capital stock of Advantage National Bank, a nationally
chartered bank with offices in Elk Grove Village and Roselle, Illinois.

         Advantage National Bank, which commenced operations on January 22,
2001, provides full-service commercial and consumer banking from its main office
in Elk Grove Village, Illinois, and its single branch office in Roselle,
Illinois. The bank's market area is comprised of the communities of Elk Grove
Village, Roselle and Bloomingdale, Illinois.

         Advantage National Bank serves the commercial banking and personal
needs of individuals, small- and medium-sized businesses, professional
organizations and governmental and public entities located within its market by
providing a broad range of commercial and personal banking services, including a
full range of deposit services, short to intermediate term commercial, real
estate and personal loans, and various related banking products, including debit
cards, money orders, traveler's checks, automated teller services, electronic
banking and safe deposit boxes.


                                       39



                                  LEGAL MATTERS

         Certain matters pertaining to the validity of the authorization and
issuance of the Wintrust common stock to be issued in the proposed merger will
be passed upon by Vedder, Price, Kaufman & Kammholz, P.C., 222 North LaSalle
Street, Chicago, Illinois 60601. Certain matters pertaining to the federal
income tax consequences of the proposed merger will be passed upon by Barack
Ferrazzano Kirschbaum Perlman & Nagelberg LLC, 333 West Wacker Drive, Chicago,
Illinois 60606.


                                     EXPERTS

         The consolidated financial statements of Wintrust as of December 31,
2002 and 2001, and for each of the years in the three years in the period ended
December 31, 2002, included in Wintrust's Annual Report on Form 10-K for the
year ended December 31, 2002, have been audited by Ernst & Young LLP,
independent auditors, as set forth in their report thereon included in
Wintrust's Annual Report on Form 10-K for the year ended December 31, 2002, and
are incorporated by reference herein in reliance upon such report given on the
authority of Ernst & Young LLP as experts in accounting and auditing.


                              SHAREHOLDER PROPOSALS

         After the merger is completed, the next annual meeting of Wintrust's
shareholders will be held in 2004. To be eligible for inclusion in Wintrust's
proxy materials for that annual meeting, any shareholder proposal must be
received at Wintrust's principal office at 727 North Bank Lane, Lake Forest,
Illinois 60045, no later than December 31, 2003.

         All shareholder proposals submitted for inclusion in Wintrust's proxy
materials will be subject to the requirements of the proxy rules adopted under
the Securities Exchange Act, and, as with any shareholder proposal, Wintrust's
articles of incorporation and by-laws and Illinois law.

         If the merger occurs, Advantage will not have another annual meeting of
shareholders. If the merger does not occur, Advantage's next meeting of
shareholders will be held in 2004. To be eligible for inclusion in Advantage's
proxy materials for that annual meeting, there is no requirement that
shareholder proposals must be made before the meeting.


                       WHERE YOU CAN FIND MORE INFORMATION

         Wintrust files annual, quarterly and current reports, proxy statements
and other information with the SEC. These filings are available to the public
over the Internet at the SEC's website at www.sec.gov. You may also read and
copy any document Wintrust files with the SEC at its public reference room
located at 450 Fifth Street, N.W., Washington D.C. 20549. Copies of these
documents also can be obtained at prescribed rates by writing to the Public
Reference Section of the SEC, at 450 Fifth Street, N.W., Washington D.C. 20549
or by calling 1-800-SEC-0330 for additional information on the operation of the
public reference facilities. Wintrust's SEC filings are also available on its
Web site at http://www.wintrust.com, and at the office of Nasdaq National
Market. For further information on obtaining copies of Wintrust's public filings
at the Nasdaq National Market, you should call (212) 656-5060.

         Wintrust filed with the SEC a registration statement on Form S-4 under
the Securities Act, as amended, to register the shares of Wintrust common stock
to be issued to Advantage shareholders in the merger. This proxy
statement/prospectus is a part of that registration statement and constitutes a
prospectus of Wintrust in addition to being a proxy statement of Advantage for
its Special Meeting. As permitted by the SEC rules, this proxy
statement/prospectus does not contain all of the information that you can find
in the registration statement or in the exhibits to the registration statement.
The additional information may be inspected and copied as set forth above.


                                       40



                INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

         The SEC allows Wintrust to incorporate by reference information into
this proxy statement/prospectus. This means that Wintrust can disclose important
information to you by referring you to another document filed separately with
the SEC. The information incorporated by reference is an important part of this
proxy statement/prospectus, except for any information superseded by information
in this proxy statement/prospectus. This proxy statement/prospectus incorporates
by reference the documents set forth below that Wintrust has filed previously
with the SEC:

         o        Wintrust's Annual Report on Form 10-K for the year ended
                  December 31, 2002 (File No. 0-21923);

         o        Wintrust's proxy statement in connection with its 2003 annual
                  meeting of shareholders filed with the SEC on April 29, 2003;

         o        Wintrust's Quarterly Report on Form 10-Q for the three months
                  ended March 31, 2003 (File No. 0-21923);

         o        Wintrust's Quarterly Report on Form 10-Q for the three months
                  ended June 30, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  January 16, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  February 4, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  April 18, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  April 24, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  May 30, 2003 (File No. 0-21923);

         o        Wintrust's Current Report on Form 8-K filed with the SEC on
                  July 17, 2003 (File No. 0-21923); and

         o        the description of (a) Wintrust's common stock contained in
                  Wintrust's Registration Statement on Form 8-A dated January 3,
                  1997 (File No. 0-21923), and (b) the associated preferred
                  share purchase rights contained in Wintrust's Registration
                  Statement on Form 8-A dated August 28, 1998 (File No.
                  0-21923).

         Wintrust also incorporates by reference any filings it makes with the
SEC pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange
Act after the date of this proxy statement/prospectus and before the Special
Meeting.

         Any statement contained in a document incorporated by reference in this
proxy statement/prospectus shall be deemed to be modified or superseded for
purposes of this proxy statement/prospectus to the extent that a statement
contained in this proxy statement/prospectus, or in any other document filed
later which is also incorporated in this proxy statement/prospectus by
reference, modifies or supersedes the statement. Any statement so modified or
superseded shall not be deemed to constitute a part of this proxy
statement/prospectus except as so modified or superseded. The information
relating to Wintrust contained in this proxy statement/prospectus should be read
together with the information in the documents incorporated in this proxy
statement/prospectus by reference.


         You may request, either orally or in writing, and Wintrust will
provide, a copy of these filings without charge by contacting David A. Dykstra,
Wintrust's Chief Operating Officer, at 727 North Bank Lane, Lake Forest,
Illinois 60045, (847) 615-4096. IF YOU WOULD LIKE TO REQUEST DOCUMENTS, PLEASE
DO SO BY SEPTEMBER 15, 2003, TO RECEIVE THEM BEFORE THE SPECIAL MEETING.


         All information concerning Wintrust and its subsidiaries has been
furnished by Wintrust, and all information concerning Advantage has been
furnished by Advantage.


                                       41



                                                                         ANNEX A











                          AGREEMENT AND PLAN OF MERGER


                                  BY AND AMONG


                         WINTRUST FINANCIAL CORPORATION,


                              WINTRUST MERGER CO.,


                                       AND


                        ADVANTAGE NATIONAL BANCORP, INC.





                               DATED JULY 2, 2003






                                TABLE OF CONTENTS

Article I     THE MERGER.....................................................A-1
       1.1    The Merger.....................................................A-1
       1.2    Effective Time.................................................A-1
       1.3    Effect of the Merger...........................................A-1
       1.4    Conversion of Shares; Merger Consideration.....................A-1
       1.5    Company Stock Options..........................................A-2
       1.6    Cancellation of Treasury Shares................................A-3
       1.7    Capital Stock of Merger Co.....................................A-3
       1.8    Recapitalization...............................................A-3
       1.9    Tax Treatment..................................................A-3
       1.10   Closing........................................................A-3

Article II    EXCHANGE OF CERTIFICATES.......................................A-3
       2.1    Wintrust to Make Shares and Cash Available.....................A-3
       2.2    No Fractional Shares...........................................A-4
       2.3    Exchange of Certificates; Surrender of Warrants................A-4

Article III   REPRESENTATIONS AND WARRANTIES CONCERNING THE COMPANY..........A-5
       3.1    Organization...................................................A-5
       3.2    Organizational Documents; Minutes and Stock Records............A-6
       3.3    Capitalization.................................................A-6
       3.4    Authorization; No Violation....................................A-6
       3.5    Consents and Approvals.........................................A-7
       3.6    Financial Statements...........................................A-7
       3.7    No Undisclosed Liabilities.....................................A-7
       3.8    Loans; Loan Loss Reserves......................................A-7
       3.9    Properties and Assets..........................................A-8
       3.10   Material Contracts.............................................A-8
       3.11   No Defaults....................................................A-9
       3.12   Conflict of Interest Transactions.............................A-10
       3.13   Investments...................................................A-10
       3.14   Compliance with Laws; Legal Proceedings.......................A-10
       3.15   Insurance.....................................................A-11
       3.16   Taxes.........................................................A-11
       3.17   Environmental Laws and Regulations............................A-11
       3.18   Community Reinvestment Act Compliance.........................A-12
       3.19   Company Regulatory Reports....................................A-12
       3.20   Employee Benefit Plans........................................A-12
       3.21   Technology and Intellectual Property..........................A-14
       3.22   No Adverse Change.............................................A-14
       3.23   Conduct of Business in Normal Course..........................A-14
       3.24   Change in Business Relationships..............................A-14
       3.25   Brokers' and Finders' Fees....................................A-14
       3.26   No Omissions..................................................A-14

Article IV    REPRESENTATIONS AND WARRANTIES CONCERNING
              WINTRUST AND MERGER CO........................................A-15
       4.1    Organization..................................................A-15
       4.2    Capitalization................................................A-15
       4.3    Authorization; No Violations..................................A-15
       4.4    Consents and Approvals........................................A-15
       4.5    Wintrust SEC Documents and Financial Statements...............A-16
       4.6    Compliance with Laws; Legal Proceedings.......................A-16
       4.7    Wintrust Regulatory Reports...................................A-17


                                       A-i


       4.8    Taxes.........................................................A-17
       4.9    Compliance with ERISA.........................................A-17
       4.10   No Defaults...................................................A-17
       4.11   Compliance with Environmental Laws............................A-17
       4.12   Fiduciary Accounts............................................A-18
       4.13   No Adverse Change.............................................A-18
       4.14   Brokers' and Finders' Fees....................................A-18
       4.15   No Omissions..................................................A-18

Article V     AGREEMENTS AND COVENANTS......................................A-18
       5.1    Conduct of Business...........................................A-18
       5.2    Access to Information.........................................A-19
       5.3    Meeting of Shareholders of the Company........................A-20
       5.4    Registration Statement and Regulatory Filings.................A-20
       5.5    Listing of Shares.............................................A-20
       5.6    Reasonable and Diligent Efforts...............................A-21
       5.7    Business Relations and Publicity..............................A-21
       5.8    No Conduct Inconsistent with this Agreement...................A-21
       5.9    Pre-Closing Loan Review.......................................A-22
       5.10   Board of Directors' Notices and Minutes.......................A-22
       5.11   Untrue Representations and Warranties.........................A-22
       5.12   Director and Officer Liability Coverage.......................A-22
       5.13   Interim Financial Statements..................................A-22
       5.14   Dissent Process...............................................A-23
       5.15   Section 368(a) Reorganization.................................A-23
       5.16   Exercise of Warrants and Options..............................A-23
       5.17   Converted Options.............................................A-23
       5.18   TM Acceptance Corp. Lease Financing Portfolio.................A-23

Article VI    EMPLOYEE BENEFIT MATTERS......................................A-24
       6.1    Benefit Plans.................................................A-24
       6.2    No Rights or Remedies.........................................A-24

Article VII   CONDITIONS PRECEDENT TO OBLIGATIONS OF WINTRUST AND MERGER CO.A-24
       7.1    Representations and Warranties; Performance of Agreements.....A-24
       7.2    Closing Certificate...........................................A-24
       7.3    Regulatory and Other Approvals................................A-24
       7.4    Approval of Merger and Delivery of Agreement..................A-25
       7.5    Effectiveness of the Registration Statement...................A-25
       7.6    No Litigation.................................................A-25
       7.7    Environmental Surveys.........................................A-25
       7.8    Opinion of Counsel............................................A-25
       7.9    Employment Agreements.........................................A-25
       7.10   No Adverse Changes............................................A-25
       7.11   Minimum Net Worth and Loan Loss Reserve Requirements..........A-25
       7.12   Voting Agreements.............................................A-26
       7.13   TM Acceptance Corp. Lease Financing Portfolio.................A-26
       7.14   Consents......................................................A-26
       7.15   Other Documents...............................................A-26

Article VIII  CONDITIONS PRECEDENT TO OBLIGATIONS OF THE COMPANY............A-26
       8.1    Representations and Warranties; Performance of Agreements.....A-26
       8.2    Closing Certificates..........................................A-26
       8.3    Regulatory and Other Approvals................................A-26
       8.4    Delivery of Agreement.........................................A-26
       8.5    Effectiveness of the Registration Statement...................A-26
       8.6    No Litigation.................................................A-26

                                      A-ii



       8.7    Opinions of Counsel...........................................A-27
       8.8    No Adverse Changes............................................A-27
       8.9    Nasdaq Listing................................................A-27
       8.10   Other Documents...............................................A-27

Article IX    NON-SURVIVAL OF REPRESENTATIONS, WARRANTIES AND COVENANTS.....A-27
       9.1    Non-Survival..................................................A-27

Article X     GENERAL.......................................................A-27
       10.1   Expenses......................................................A-27
       10.2   Termination...................................................A-29
       10.3   Confidential Information......................................A-29
       10.4   Non-Assignment................................................A-29
       10.5   Notices.......................................................A-29
       10.6   Counterparts..................................................A-30
       10.7   Knowledge.....................................................A-30
       10.8   Entire Agreement..............................................A-30
       10.9   Governing Law.................................................A-30
       10.10  Severability..................................................A-30

                                     A-iii



                                  DEFINED TERMS

Acquisition Proposal........................................................A-21
Agreement....................................................................A-1
ANB Mortgage.................................................................A-5
Articles of Merger...........................................................A-1
Bank.........................................................................A-5
Benefit Plans...............................................................A-13
BHCA.........................................................................A-5
CERCLA......................................................................A-12
Closing......................................................................A-3
Closing Date.................................................................A-3
Code.........................................................................A-1
Commission...................................................................A-7
Company......................................................................A-1
Company Board................................................................A-6
Company Common Stock.........................................................A-1
Company Regulatory Reports..................................................A-12
Company Stock Certificates...................................................A-3
Company Stock Option Plan....................................................A-2
Confidentiality Agreement...................................................A-19
Conversion Fund..............................................................A-4
Converted Option.............................................................A-2
CRA.........................................................................A-12
DEFINED TERMS................................................................B-1
Effective Time...............................................................A-1
Employees...................................................................A-24
Encumbrances.................................................................A-8
Environmental Laws..........................................................A-11
ERISA Affiliate.............................................................A-13
ERISA Plans.................................................................A-12
Exchange Act................................................................A-16
Exchange Agent...............................................................A-3
Exchange Ratio...............................................................A-1
Federal Reserve..............................................................A-7
Federal Reserve Application..................................................A-7
Financial Statements.........................................................A-7
GAAP.........................................................................A-5
Governmental Authority.......................................................A-7
Hazardous Substance.........................................................A-12
Illinois Act.................................................................A-1
Intellectual Property.......................................................A-14
Interim Balance Sheet........................................................A-7
Interim Financial Statements.................................................A-7
Investment Securities.......................................................A-10
knowledge...................................................................A-30
Loans........................................................................A-7
Material Adverse Effect......................................................A-5
Material Contracts...........................................................A-8
Merger.......................................................................A-1
Merger Co....................................................................A-1
OCC.........................................................................A-12
Option Conversion Agreement..................................................A-3
OREO.........................................................................A-8
Outstanding Company Option...................................................A-2

                                      A-iv



Parties......................................................................A-1
Permitted Encumbrances.......................................................A-8
Plan Amendment...............................................................A-3
Program Agreement...........................................................A-23
Proxy Statement/Prospectus...................................................A-7
Recapitalization.............................................................A-3
Registration Statement......................................................A-20
Retained Plans..............................................................A-24
Returns.....................................................................A-11
Securities Act...............................................................A-7
Shareholders Meeting........................................................A-20
Subsidiaries.................................................................A-6
Superior Acquisition Proposal...............................................A-21
Surviving Corporation........................................................A-1
Warrant Cancellation Agreement...............................................A-2
Warrant Consideration........................................................A-2
Warrants.....................................................................A-6
Wintrust.....................................................................A-1
Wintrust Bank...............................................................A-16
Wintrust Common Stock........................................................A-1
Wintrust Common Stock Price..................................................A-2
Wintrust Regulatory Reports.................................................A-17
Wintrust SEC Documents......................................................A-16
Wintrust Stock Certificates..................................................A-3

                                      A-v




                              DISCLOSURE SCHEDULES


Schedule of Warrant Holders...............................................3.3(a)
Authorization; No Violation..................................................3.4
Consents and Approvals.......................................................3.5
Financial Statements.........................................................3.6
Undisclosed Liabilities......................................................3.7
Loans; Loan Loss Reserves....................................................3.8
Schedule of Real Property.................................................3.9(a)
Schedule of Intangible Personal Property..................................3.9(b)
Schedule of Material Contracts..............................................3.10
Schedule of Interested Transactions.........................................3.12
Investments.................................................................3.13
Legal Proceedings........................................................3.14(b)
Schedule of Insurance.......................................................3.15
Environmental Laws and Regulations..........................................3.17
Employee Benefit Plans......................................................3.20
Schedule of Intellectual Property...........................................3.21
Wintrust Exceptions Regarding Material Contracts..........................4.5(d)
Wintrust Disclosure Regarding Enforcement Actions.........................4.6(b)
Wintrust Compliance with Environmental Laws.................................4.11
Wintrust Finder's Fees......................................................4.14
Proposed ISS Investment...................................................5.1(h)
Employees....................................................................6.1
Key Management Personnel.....................................................7.9
Voting Agreement Signatories................................................7.12


                                    EXHIBITS

Exhibit A.................................Form of Warrant Cancellation Agreement
Exhibit B....................................Form of Option Conversion Agreement
Exhibit C.....................................Form of Opinion of Company Counsel
Exhibit D............................Form of Key Management Employment Agreement
Exhibit E...............................................Form of Voting Agreement
Exhibit F....................................Form of Opinion of Wintrust Counsel


                                      A-vi



                          AGREEMENT AND PLAN OF MERGER

         This AGREEMENT AND PLAN OF MERGER (this "Agreement"), is entered into
as of the 2nd day of July, 2003, by and among WINTRUST FINANCIAL CORPORATION, an
Illinois corporation ("Wintrust"), WINTRUST MERGER CO., an Illinois corporation
and wholly owned subsidiary of Wintrust ("Merger Co."), and ADVANTAGE NATIONAL
BANCORP, INC., an Illinois corporation (the "Company"). Wintrust, Merger Co.,
and the Company are referred to collectively in this Agreement as the "Parties."


                                    RECITALS

         WHEREAS, the boards of directors of each of the Parties have approved
and declared it advisable and in the best interest of the Parties and their
respective shareholders to effect a reorganization, whereby Merger Co. will
merge with and into the Company, in the manner and on the terms and subject to
the conditions set forth in Article I below (the "Merger"), as a result of which
the Company will become a wholly owned subsidiary of Wintrust.

         WHEREAS, for federal income tax purposes the Parties desire and intend
that the Merger qualify as a reorganization in accordance with Section 368(a) of
the Internal Revenue Code of 1986, as amended (the "Code").


         NOW THEREFORE, in consideration of the premises and the mutual promises
herein made, and in consideration of the representations, warranties and
covenants herein contained, the Parties agree as follows.



                                    ARTICLE I
                                   THE MERGER

         1.1 The Merger. At the Effective Time (as defined in Section 1.2), in
accordance with this Agreement and the Illinois Business Corporation Act (the
"Illinois Act"), Merger Co. shall be merged with and into the Company, and the
Company shall continue as the corporation surviving the Merger (the "Surviving
Corporation"), and shall be a wholly owned subsidiary of Wintrust.

         1.2 Effective Time. As of the Closing, the Parties will cause articles
of merger (the "Articles of Merger") with respect to the Merger to be executed
and filed with the Secretary of State of the State of Illinois as provided in
the Illinois Act. The Merger shall become effective on the date and time at
which the Articles of Merger are duly filed by the Secretary of State of the
State of Illinois, or at such other date and time as is agreed among the Parties
and specified in the Articles of Merger (the "Effective Time").

         1.3 Effect of the Merger. At and after the Effective Time:

                  (a) the Merger shall have the effect set forth in Section
         11.50 of the Illinois Act;

                  (b) the articles of incorporation and by-laws of Merger Co.,
         copies of which have been previously provided to the Company, as in
         effect immediately prior to the Effective Time shall be the articles of
         incorporation and by-laws of the Surviving Corporation until thereafter
         amended as provided therein or by applicable law; and

                  (c) the directors and officers of the Company immediately
         prior to the Effective Time shall be the directors and officers of the
         Surviving Corporation until their successors have been duly elected or
         appointed and qualified, or until their earlier death, resignation or
         removal in accordance with the articles of incorporation and the
         by-laws of the Surviving Corporation.

         1.4 Conversion of Shares; Merger Consideration.

                  (a) Wintrust Common Stock. At the Effective Time, each share
         of common stock of the Company, par value $5.00 per share ("Company
         Common Stock"), issued and outstanding immediately prior to the
         Effective Time shall by reason of the Merger and without any action by
         the holder thereof, be converted into the right to receive that number
         (the "Exchange Ratio") of shares, rounded to the nearest one thousandth
         of a share, of common stock of Wintrust ("Wintrust Common Stock"),
         determined as follows:


                                      A-1



                           (i) If the unweighted average of the high and low
                  sale prices of a share of Wintrust Common Stock as reported on
                  the Nasdaq National Market for each of the ten trading days
                  ending on the second trading day preceding the Closing Date
                  (as defined in Section 1.10) (the "Wintrust Common Stock
                  Price") is at least $25.00 and no more than $35.00, the
                  Exchange Ratio shall be equal to the quotient of $26.50
                  divided by the Wintrust Common Stock Price.

                           (ii) If the Wintrust Common Stock Price is less than
                  $25.00, the Exchange Ratio shall be equal to the quotient of
                  $26.50 divided by $25.00.

                           (iii) If the Wintrust Common Stock Price is greater
                  than $35.00, the Exchange Ratio shall be equal to the quotient
                  of $26.50 divided by $35.00.

                  (b) Warrant Consideration.

                           (i) Each Warrant (as defined in Section 3.3)
                  outstanding at the Effective Time for the purchase of shares
                  of Company Common Stock shall be converted into the right to
                  receive an amount (the "Warrant Consideration") in cash equal
                  to the number of shares of Company Common Stock subject to
                  such Warrant multiplied by the difference between (i) $26.50
                  and (ii) the per share exercise price associated with such
                  Warrant.

                           (ii) The Company shall provide to Wintrust, not less
                  than five (5) business days prior to the Closing Date, copies
                  of an agreement in the form of Exhibit A attached hereto (the
                  "Warrant Cancellation Agreement") executed by each of the
                  holders of outstanding Warrants acknowledging their agreement
                  and consent to such terms of conversion.

                  (c) Effect on Capital Stock. All of the shares of Company
         Common Stock converted into Wintrust Common Stock in accordance with
         this Article I shall no longer be outstanding and shall automatically
         be cancelled and retired and shall cease to exist as of the Effective
         Time, and each certificate previously representing any such shares of
         Company Common Stock shall cease to have any rights with respect
         thereto, except the right to (i) receive, in accordance with Section
         2.3(a), a certificate representing the number of whole shares of
         Wintrust Common Stock determined pursuant to this Section 1.4 and cash
         in lieu of any fractional shares thereof determined pursuant to Section
         2.2, or (ii) exercise dissenters' rights in accordance with, and
         subject to the provisions of, the Illinois Act.

         1.5 Company Stock Options.

                  (a) At the Effective Time, each option granted by the Company
         under the terms of the Advantage National Bancorp, Inc. 2002 Stock
         Incentive Plan (the "Company Option Plan") to purchase shares of
         Company Common Stock that is outstanding and unexercised immediately
         prior to the Effective Time (an "Outstanding Company Option"), shall be
         converted into an option to purchase shares of Wintrust Common Stock (a
         "Converted Option"), in such number and at such exercise price as set
         forth herein, and otherwise having the same terms and conditions as in
         effect immediately prior to the Effective Time except to the extent
         that (i) such Outstanding Company Options shall be altered in
         accordance with their terms as a result of the Merger contemplated
         hereby, as follows: (1) the number of shares of Wintrust Common Stock
         to be subject to the Converted Option shall be equal to the product of
         (A) the number of shares of Company Common Stock subject to the
         original Outstanding Company Option and (B) the Exchange Ratio; (2) the
         exercise price per share of Wintrust Common Stock under the Converted
         Option shall be equal to (A) the exercise price per share of Company
         Common Stock under the original Outstanding Company Option divided by
         (B) the Exchange Ratio; and (3) upon exercise of each Converted Option
         by a holder thereof, the aggregate number of shares of Wintrust Common
         Stock deliverable upon such exercise shall be rounded down, if
         necessary, to the nearest whole share and the aggregate exercise price
         shall be rounded up, if necessary, to the nearest cent, and (ii) the
         vesting of Outstanding Company Options held immediately prior to the
         Effective Time (1) by all directors of the Company and (2) by all
         employees of the Company other than those unvested Outstanding Company
         Options held by Gerhardt E. Umlauf pursuant to his employment agreement
         with the Company and each of Paul Katauskas and Mark Stetson pursuant
         to their employment agreements dated June 17, 2003, shall be
         accelerated such that all of such Outstanding Company Options to the
         extent not previously vested shall become fully vested and immediately
         exercisable at the Effective Time.


                                      A-2



                  (b) The adjustments provided herein with respect to any
         Outstanding Company Options that are "incentive stock options" (as
         defined in Section 422 of the Code) shall be effected in a manner
         consistent with the requirements of Section 424(a) of the Code.

                  (c) The Company Option Plan shall be amended, effective as of
         the Effective Time, to provide for the conversion of Outstanding
         Company Options in accordance with Section 1.5(a) (the "Plan
         Amendment"). The Company shall provide to Wintrust, not less than five
         (5) business days prior to the Closing Date, copies of an agreement in
         the form of Exhibit B attached hereto (the "Option Conversion
         Agreement") from each of the holders of Outstanding Company Options
         acknowledging their agreement and consent to the Plan Amendment and to
         such terms of conversion set forth in this Section 1.5.

         1.6 Cancellation of Treasury Shares. At the Effective Time, each share
of Company Common Stock held as treasury stock, if any, immediately prior to the
Effective Time shall automatically be cancelled and retired and cease to exist,
and no shares of Wintrust Common Stock or other consideration shall be exchanged
therefor.

         1.7 Capital Stock of Merger Co. Each share of common stock of Merger
Co. issued and outstanding immediately prior to the Effective Time shall be
converted into and become one share of common stock, par value $1.00, of the
Surviving Corporation with the same rights, powers and privileges as the shares
so converted and shall constitute the only outstanding capital stock of the
Surviving Corporation.

         1.8 Recapitalization. In the event that Wintrust changes (or
establishes a record date for changing) the number of shares of Wintrust Common
Stock issued and outstanding as a result of a stock dividend, stock split,
recapitalization, reclassification, combination or similar transaction with
respect to the outstanding shares of Wintrust Common Stock (a
"Recapitalization"), and the record date therefor shall be after the date of
this Agreement and prior to the commencement of the ten trading day-period
during which the Exchange Ratio is determined, then the conversion provisions
described in Section 1.4(a) shall be appropriately and proportionately adjusted.
Wintrust agrees it shall not effect, establish a record date to effect, or
announce a Recapitalization (or record date therefor) during the ten trading
day-period during which the Exchange Ratio is determined.

         1.9 Tax Treatment. It is intended that the Merger shall constitute a
reorganization within the meaning Section 368(a) of the Code, and that this
Agreement shall constitute a "plan of reorganization" for purposes of Section
368 of the Code.

         1.10 Closing. The consummation of the transactions contemplated by this
Agreement shall take place at a closing (the "Closing") to be held on the fifth
business day following the date on which all of the conditions set forth in
Sections 7.3 and 7.4 of this Agreement have been satisfied or on such other date
as Wintrust and the Company may mutually agree (the "Closing Date"). In the
event of the filing of any motion for rehearing or any appeal from the decision
of any regulatory authority approving the transactions contemplated in this
Agreement or any legal proceedings of the type contemplated by Sections 7.6 or
8.6, Wintrust or the Company may postpone the Closing by written notice to the
other parties until such approvals have been obtained or such motion, appeal or
litigation has been resolved, but in no event shall such Closing be postponed
beyond the close of business on December 31, 2003 (except as may be extended
pursuant to Section 10.2(b)) without the consent of the boards of directors of
Wintrust and the Company. The Closing shall take place at 10:00 a.m., local
time, on the Closing Date at the offices of Schiff Hardin & Waite, 6600 Sears
Tower, Chicago, Illinois, or at such other place and time upon which the parties
may agree.


                                   ARTICLE II
                            EXCHANGE OF CERTIFICATES

         2.1 Wintrust to Make Shares and Cash Available. At or prior to the
Effective Time, Wintrust shall authorize the issuance of and shall make
available to the Illinois Stock Transfer Company (the "Exchange Agent"), for the
benefit of the holders of certificates of Company Common Stock (the "Company
Stock Certificates") and the Warrants, for exchange in accordance with this
Article II, a sufficient number of certificates for shares of Wintrust Common
Stock (the "Wintrust Stock Certificates") to be issued pursuant to Section
1.4(a), and sufficient cash for payment of (a) the Warrant Consideration in
accordance with Section 1.4(b) and (b) cash in lieu of any fractional shares of
Wintrust Common Stock in accordance with Section 2.2. Such Wintrust Stock
Certificates and cash,


                                      A-3


together with any dividends or distributions with respect thereto paid after the
Effective Time, are referred to in this Article II as the "Conversion Fund."
Wintrust shall be solely responsible for the payment of any fees and expenses of
the Exchange Agent.

         2.2 No Fractional Shares. Notwithstanding anything to the contrary
contained in this Agreement, no fractional shares of Wintrust Common Stock shall
be issued in the Merger. Each holder of shares of Company Common Stock who would
otherwise be entitled to receive a fractional part of a share of Wintrust Common
Stock pursuant to Section 1.4(a) shall instead be entitled to receive an amount
in cash (without interest) rounded to the nearest whole cent, determined by
multiplying the Wintrust Common Stock Price (as determined in accordance with
Section 1.4(a)) by the fractional share of Wintrust Common Stock to which such
former holder would otherwise be entitled.

         2.3 Exchange of Certificates; Surrender of Warrants.

                  (a) As soon as practicable after the Effective Time, and in no
         event later than five (5) business days thereafter, the Surviving
         Corporation shall cause the Exchange Agent to mail to each holder of
         record of one or more Company Stock Certificates or Warrants a letter
         of transmittal (which shall specify that delivery shall be effected,
         and risk of loss and title to Company Stock Certificates and/or
         Warrants shall pass, only upon delivery of such certificates and/or
         Warrants to the Exchange Agent) and instructions for use in effecting
         the surrender of the Company Stock Certificates and the Warrants
         pursuant to this Agreement.

                           (i) Upon proper surrender of a Company Stock
                  Certificate for exchange to the Exchange Agent, together with
                  such properly completed letter of transmittal, duly executed,
                  the holder of such Company Stock Certificate shall be entitled
                  to receive in exchange therefor, as applicable, (1) a Wintrust
                  Stock Certificate representing that number of whole shares of
                  Wintrust Common Stock to which such holder of Company Common
                  Stock shall have become entitled pursuant to Section 1.4(a)
                  (after taking into account all shares of Company Common Stock
                  then held by such holder), and (2) a check representing the
                  amount of any cash in lieu of fractional shares that such
                  holder has the right to receive pursuant to Section 2.2 in
                  respect of such Company Stock Certificate, and the Company
                  Stock Certificate so surrendered shall forthwith be canceled.
                  No interest will be paid or accrued on any cash in lieu of
                  fractional shares payable to holders of Company Stock
                  Certificates.

                           (ii) Upon proper surrender of a Warrant for exchange
                  to the Exchange Agent, together with such properly completed
                  letter of transmittal, duly executed, the holder of such
                  Warrant shall be entitled to receive in exchange therefor a
                  check representing the amount of Warrant Consideration to
                  which such holder shall have become entitled pursuant to
                  Section 1.4(b) (after taking into account all Warrants then
                  held by such holder), and the Warrant so surrendered shall
                  forthwith be canceled. No interest will be paid or accrued on
                  any Warrant Consideration payable to holders of Warrants.

                  (b) If any Wintrust Stock Certificate is to be issued in a
         name other than that in which the Company Stock Certificate surrendered
         in exchange therefor is registered, it shall be a condition of the
         issuance thereof that the Company Stock Certificate so surrendered
         shall be properly endorsed (or accompanied by an appropriate instrument
         of transfer) and otherwise in proper form for transfer, and that the
         person requesting such exchange shall pay to the Exchange Agent in
         advance any transfer or other taxes required by reason of the issuance
         of a Wintrust Stock Certificate in any name other than that of the
         registered holder of the Company Stock Certificate surrendered, or
         required for any other reason, or shall establish to the satisfaction
         of the Exchange Agent that such tax has been paid or is not payable.

                  (c) After the Effective Time, there shall be no transfers on
         the stock transfer books of the Company of the shares of Company Common
         Stock or Warrants that were issued and outstanding immediately prior to
         the Effective Time.

                  (d) Any portion of the Conversion Fund that remains unclaimed
         by the shareholders of the Company for twelve (12) months after the
         Effective Time shall be paid to the Surviving Corporation. Any
         shareholders of the Company who have not theretofore complied with this
         Article II shall thereafter look only to the Surviving Corporation for
         the issuance of certificates representing shares of Wintrust Common
         Stock and the payment of cash in lieu of any fractional shares and any
         unpaid dividends and distributions on Wintrust Common


                                      A-4


         Stock deliverable in respect of each share of Company Common Stock such
         shareholder holds as determined pursuant to this Agreement, in each
         case, without any interest thereon, and any holders of Warrants who
         have not theretofore complied with this Article II shall thereafter
         look only to the Surviving Corporation for the payment of the Warrant
         Consideration, without any interest thereon. Notwithstanding the
         foregoing, none of Wintrust, the Surviving Corporation, the Company,
         the Exchange Agent or any other person shall be liable to any former
         holder of shares of Company Common Stock or Warrants, for any amount
         delivered in good faith to a public official pursuant to applicable
         abandoned property, escheat or similar laws.

                  (e) In the event any Company Stock Certificate or Warrant
         shall have been lost, stolen or destroyed, upon the making of an
         affidavit of that fact by the person claiming such Company Stock
         Certificate or Warrant to be lost, stolen or destroyed and, if
         reasonably required by the Surviving Corporation, the posting by such
         person of a bond in such amount as the Exchange Agent may determine is
         reasonably necessary as indemnity against any claim that may be made
         against it with respect to such Company Stock Certificate or Warrant,
         the Exchange Agent will issue in exchange for (i) such lost, stolen or
         destroyed Company Stock Certificate, a Wintrust Stock Certificate
         representing the shares of Wintrust Common Stock and cash in lieu of
         any fractional shares deliverable in respect thereof pursuant to this
         Agreement, or (ii) such lost, stolen or destroyed Warrant, the Warrant
         Consideration to which such holder shall have become entitled pursuant
         to Section 1.4(b).

                  (f) No dividends or other distributions declared with respect
         to Wintrust Common Stock and payable to the holders of record thereof
         after the Effective Time shall be paid to the holder of any
         unsurrendered Company Stock Certificate until the holder thereof shall
         surrender such Company Stock Certificate in accordance with this
         Article II. Promptly after the surrender of a Company Stock Certificate
         in accordance with this Article II, the record holder thereof shall be
         entitled to receive any such dividends or other distributions, without
         interest thereon, which theretofore had become payable with respect to
         shares of Wintrust Common Stock represented by such Company Stock
         Certificate. No holder of an unsurrendered Company Stock Certificate
         shall be entitled, until the surrender of such Company Stock
         Certificate, to vote the shares of Wintrust Common Stock into which
         Company Common Stock shall have been converted.


                                   ARTICLE III
                         REPRESENTATIONS AND WARRANTIES
                             CONCERNING THE COMPANY

         The Company hereby represents and warrants to Wintrust and Merger Co.
as follows:

         3.1 Organization.

                  (a) The Company is duly registered as a bank holding company
         under the Bank Holding Company Act of 1956, as amended (the "BHCA"), is
         a corporation duly organized, validly existing and in good standing
         under the laws of the State of Illinois, and has the corporate power
         and authority to own its properties and to carry on its business as
         presently conducted. The Company is duly qualified and in good standing
         as a foreign corporation in each other jurisdiction where the location
         and character of its properties and the business conducted by it
         require such qualification, except where the failure to be so qualified
         would not have a Material Adverse Effect on the Company. As used in
         this Agreement, "Material Adverse Effect" shall mean a material adverse
         effect on (i) the business, assets, properties, results of operations
         or financial condition of a Party and its subsidiaries, taken as a
         whole, or (ii) on the consummation of the Merger, but shall exclude any
         such material adverse effect resulting from: (1) a change with respect
         to, or effect on, a Party resulting from a change in applicable laws,
         rules or regulations, generally accepted accounting principles ("GAAP")
         or regulatory accounting principles, as such would apply to the
         financial statements of a Party on a consolidated basis; (2) a change
         with respect to, or effect on, a Party resulting from expenses (such as
         legal or accounting fees) incurred in connection with the transactions
         contemplated by this Agreement, including the costs of litigation
         defending any of the transactions contemplated herein; (3) a change
         with respect to, or effect on, a Party resulting from any other matter
         affecting depository institutions generally (including financial
         institutions and their holding companies) including changes in general
         economic conditions and changes in prevailing interest and deposit
         rates; and (4) actions or omissions taken by a Party as required
         hereunder.

                  (b) Other than (i) Advantage National Bank (the "Bank"), (ii)
         a 50% ownership interest by the Bank in Advantage National Bank
         Mortgage, LLC ("ANB Mortgage," and together with the Bank, the


                                      A-5



         "Subsidiaries"), and (iii) stock of the Federal Home Loan Bank of
         Chicago and the Federal Reserve Bank of Chicago owned by the
         Bank, the Company does not own, whether directly or indirectly, any
         voting stock, equity securities or membership, partnership, joint
         venture or similar ownership interest in any corporation, association,
         partnership, limited liability company or other entity.

                  (c) The Bank is a national banking association, duly chartered
         and organized, validly existing and currently authorized to transact
         the business of banking under the National Banking Act, and has the
         requisite power and authority to own its properties and to carry on its
         business as presently conducted.

         3.2 Organizational Documents; Minutes and Stock Records. The Company
has furnished Wintrust with copies of the articles of incorporation and by-laws
of the Company and the articles of association and by-laws of the Bank, in each
case as amended to the date hereof, and with such other documents as requested
by Wintrust relating to the authority of the Company and the Bank to conduct
their respective businesses. All such documents are complete and correct. The
stock registers and minute books of the Company and the Bank are each complete,
correct and accurately reflect, in each case in all material respects, all
meetings, consents, and other actions of the organizers, incorporators,
shareholders, board of directors, and committees of the board of directors of
the Company and the Bank, respectively, and all transactions reported to the
Company or the Bank, as the case may be, by its respective shareholders, in such
entity's capital stock occurring since the initial organization of the Company
and the Bank, respectively.

         3.3 Capitalization.

                  (a) The Company. The authorized capital stock of the Company
         consists of (i) 3,000,000 shares of common stock, par value $5.00 per
         share, of which 729,389 shares are issued and outstanding as of the
         date of this Agreement, (ii) 100,000 shares of preferred stock, par
         value $5.00 per share, of which no shares are issued and outstanding,
         and (iii) no shares are held in treasury. The issued and outstanding
         shares of Company Common Stock have been duly and validly authorized
         and issued and are fully paid and nonassessable. The Company has issued
         and has outstanding warrants for the purchase of 189,614 shares of
         Company Common Stock (the "Warrants"), the beneficial and record
         holders of which are set forth on Schedule 3.3(a). The Warrants have
         been duly authorized by all necessary corporate action (including
         shareholder approval if necessary), have been validly executed, issued
         and delivered by the Company, constitute the legal, valid and binding
         obligations of the Company, and are enforceable as to the Company in
         accordance with their terms. The shares of Company Common Stock to be
         issued upon exercise of the Warrants are validly authorized and, upon
         such exercise of the Warrants in accordance with their terms, will be
         validly issued, fully paid, and nonassessable. The Company Common Stock
         is subject to no preferences, qualifications, limitations, restrictions
         or special or relative rights under the Company's articles of
         incorporation. Except for the Warrants and the Outstanding Company
         Options under the Company Option Plan, there are no options,
         agreements, contracts, or other rights in existence to purchase or
         acquire from the Company any shares of capital stock of the Company,
         whether now or hereafter authorized or issued.

                  (b) The Bank. The authorized capital stock of the Bank
         consists of 1,500,000 shares of common stock, par value $5.00 per
         share, of which 725,723 are issued and outstanding and no shares are
         held in treasury. The issued and outstanding shares of common stock of
         the Bank have been duly and validly authorized and issued and are fully
         paid and nonassessable (except as provided in 12 U.S.C. ss.55) and
         owned by the Company. There are no options, agreements, contracts, or
         other rights in existence to purchase or acquire from the Bank any
         shares of capital stock of the Bank, whether now or hereafter
         authorized or issued. Other than shares of the Federal Reserve Bank of
         Chicago and the Federal Home Loan Bank of Chicago and a 50% ownership
         interest in ANB Mortgage, the Bank does not own, whether directly or
         indirectly, any voting stock, equity securities or membership,
         partnership, joint venture or similar ownership interest in any
         corporation, association, partnership, limited liability company or
         other entity.

         3.4 Authorization; No Violation. The execution and delivery of this
Agreement and the performance of the Company's obligations hereunder have been
duly and validly authorized by the Board of Directors of the Company (the
"Company Board"), and do not violate or conflict with the Company's articles of
incorporation, by-laws, the Illinois Act, or any applicable law, court order or
decree to which the Company or the Bank is a party or subject, or by which the
Company, the Bank or their respective properties are bound, subject to the
approval of this Agreement and the Merger by the shareholders of the Company.
Except as set forth on Schedule 3.4, the execution and delivery of this
Agreement and the performance of the Company's obligations hereunder do not and
will not
or


                                      A-6


result in any default or give rise to any right of termination, cancellation or
acceleration under any material note, bond, mortgage, indenture other agreement
by which the Company, the Bank or their respective properties are bound. This
Agreement, when executed and delivered, and subject to the regulatory approvals
described in Section 7.3, will be a valid, binding and enforceable obligation of
the Company, subject to applicable bankruptcy, insolvency, reorganization,
moratorium or similar laws affecting creditors generally and to general
principles of equity.

         3.5 Consents and Approvals. Except as set forth on Schedule 3.5, no
consents or approvals of, or filings or registrations with, any court,
administrative agency or commission or other governmental authority or
instrumentality (each, a "Governmental Authority") or with any third party are
necessary in connection with the execution and delivery by the Company of this
Agreement and the consummation by the Company of the Merger except for (a) the
filing by Wintrust of an application (the "Federal Reserve Application") with
the Board of Governors of the Federal Reserve System (the "Federal Reserve")
under the BHCA, (b) the filing with the Securities and Exchange Commission (the
"Commission") of a proxy statement in definitive form and a registration
statement on an appropriate form under the Securities Act of 1933, as amended
(the "Securities Act"), relating to the meeting of the Company's shareholders to
be held in connection with this Agreement and the Merger and the registration of
the shares of Wintrust Common Stock (the "Proxy Statement/Prospectus"), (c) the
filing of the Articles of Merger with the Secretary of State of the State of
Illinois under the Illinois Act, and (d) the approval of this Agreement and the
Merger by the requisite vote of the shareholders of the Company.

         3.6 Financial Statements. Schedule 3.6 sets forth true and complete
copies of the following financial statements (collectively, the "Financial
Statements"): (a) the audited balance sheets of the Bank as of December 31, 2002
and 2001 and the related statements of income, changes in stockholders' equity
and cash flows for the fiscal years then ended, and (b) the unaudited
consolidated interim balance sheet of the Company as of March 31, 2003 (the
"Interim Balance Sheet") and the related statement of income and changes in
stockholders' equity for the three-month period then ended (together with the
Interim Balance Sheet, the "Interim Financial Statements"). The Financial
Statements are complete and correct as of their respective dates and have been
prepared in conformity with GAAP applied on a consistent basis throughout the
periods involved. Each balance sheet (including any related notes) included in
the Financial Statements presents fairly the financial position of the Company
as of the date thereof, and each income statement (including any related notes)
and statement of cash flow included in the Financial Statements presents fairly
the results of operations and cash flow, respectively, of the Company for the
period set forth therein; provided, however, that the Interim Financial
Statements contain all adjustments necessary for a fair presentation, subject to
normal, recurring year-end adjustments (which adjustments will not be,
individually or in the aggregate, material), and lack footnotes. Each of the
audited Financial Statements has been certified by the Company's independent
auditor, and each of the Interim Financial Statements has been certified by the
Company's chief executive officer and principal accounting officer. The books,
records and accounts of the Company accurately and fairly reflect, in reasonable
detail, all transactions and all items of income and expense, assets and
liabilities and accruals relating to the Company.

         3.7 No Undisclosed Liabilities. Except as set forth on Schedule 3.7,
the Company has no liabilities, whether accrued, absolute, contingent, or
otherwise, existing or arising out of any transaction or state of facts existing
on or prior to the date hereof, except (a) as and to the extent disclosed,
reflected or reserved against in the Financial Statements, (b) as and to the
extent arising under contracts, commitments, transactions, or circumstances
identified in the Schedules provided for herein, excluding any liabilities for
Company breaches thereunder, and (c) liabilities, not material in the aggregate
and incurred in the ordinary course of business, which, under GAAP, would not be
required to be reflected on a balance sheet prepared as of the date hereof. For
purposes of the preceding subsection (c), any liabilities incurred in connection
with litigation or judicial, administrative or arbitration proceedings or claims
against the Company shall not be deemed to be incurred in the ordinary course of
business.

         3.8 Loans; Loan Loss Reserves.


                  (a) Except as set forth on Schedule 3.8, each outstanding
         loan, loan agreement, note, lease or other borrowing agreement, any
         participation therein and any guaranty, renewal or extension thereof
         (collectively, "Loans") reflected on the books and records of the Bank
         is evidenced by appropriate and sufficient documentation and
         constitutes the legal, valid and binding obligation of the obligor
         named therein, enforceable in accordance with its terms, except to the
         extent such enforceability may be limited by applicable bankruptcy,
         insolvency, reorganization, moratorium or other similar laws affecting
         the enforcement of creditors' rights and remedies


                                      A-7


         generally from time to time in effect and by applicable laws which may
         affect the availability of equitable remedies. No obligor named in any
         Loan has provided notice (whether written or, to the knowledge of the
         Company, oral) to the Company or the Bank that such obligor intends to
         attempt to avoid the enforceability of any term of any Loan under any
         such laws or equitable remedies, and no Loan is subject to any valid
         defense, set-off, or counterclaim that has been asserted with respect
         to such Loan. All Loans that are secured, as evidenced by the
         appropriate and sufficient ancillary security documents, are so secured
         by valid and enforceable liens. Neither the Bank nor the Company has
         entered into any loan repurchase agreements.


                  (b) The allowance for loan and lease losses shown on each of
         the balance sheets contained in the Financial Statements are adequate
         under the requirements under GAAP to provide for possible losses, net
         of recoveries relating to loans and leases previously charged off on
         loans and leases outstanding (including accrued interest receivable) as
         of the applicable date of such balance sheet. The aggregate loan and
         lease balances of the Bank as of March 31, 2003 in excess of such
         reserves as shown on the Interim Balance Sheet are, to the knowledge of
         the Company, collectible in accordance with their respective terms.

         3.9 Properties and Assets.

                  (a) Real Property. Attached as Schedule 3.9(a) is a Schedule
         of Real Property, which sets forth a complete and correct description
         of all real property owned or leased by the Company or the Bank or in
         which either the Company or the Bank has an interest (other than as a
         mortgagee), including all real property carried by the Bank as Other
         Real Estate Owned ("OREO"). The Company and the Bank own, or have a
         valid right to use or a leasehold interest in, all real property used
         by them in the conduct of their respective businesses as such
         businesses are presently conducted. Except as otherwise set forth on
         Schedule 3.9(a), the ownership or leasehold interest of the Company or
         the Bank in such real property (excluding OREO) is not subject to any
         mortgage, pledge, lien, option, conditional sale agreement,
         encumbrance, security interest, title exceptions or restrictions or
         claims or charges of any kind (collectively, "Encumbrances"), except
         for Permitted Encumbrances. As used in this Agreement, "Permitted
         Encumbrances" shall mean (i) Encumbrances arising under conditional
         sales contracts and equipment leases with third parties under which the
         Company or the Bank is not delinquent or in default, (ii) carriers',
         workers', repairers', materialmen's, warehousemen liens' and similar
         Encumbrances incurred in the ordinary course of business, (iii)
         Encumbrances for taxes not yet due and payable, or that are being
         contested in good faith and for which proper reserves have been
         established and reflected on the Interim Balance Sheet, (iv) minor
         defects in title to real property that do not materially impair the
         intended use thereof, (v) zoning and similar restrictions on the use of
         real property, and (vi) Encumbrances created in the ordinary course of
         business to secure obligations of the Company or the Bank. All
         certificates, licenses and permits required for the lawful use and
         occupancy of any real property by the Company or the Bank, as the case
         may be, have been obtained and are in full force and effect. Except as
         otherwise set forth on Schedule 3.9(a), all OREO is the subject of a
         recent appraisal that complies with applicable regulatory requirements
         and is carried on the Bank's books at an amount which does not exceed
         its current appraised value.

                  (b) Personal Property. Attached as Schedule 3.9(b)(i) is a
         Schedule of Tangible Personal Property which sets forth a complete and
         correct description of each item of tangible personal property owned by
         the Company or the Bank or used by the Company or the Bank in the
         conduct of their businesses that is reflected as a capital asset on the
         Interim Balance Sheet and is being depreciated for tax purposes. Except
         as otherwise set forth on Schedule 3.9(b)(ii), all such personal
         property is owned by the Company or the Bank, all such property is
         owned free and clear of any Encumbrances except for Permitted
         Encumbrances, and all such property is in good working condition,
         normal wear and tear excepted.

                  (c) Assets. The assets reflected on the Interim Balance Sheet
         or identified in this Agreement or on the Schedules provided for herein
         include all of the material assets (i) owned by the Company or the
         Bank, except for those subsequently disposed of by the Company or the
         Bank for fair value in the ordinary course of business, and (2) used or
         intended for use by the Company or the Bank in the conduct of their
         respective businesses.

         3.10 Material Contracts. Attached as Schedule 3.10 is a Schedule of
Material Contracts. The Company has previously delivered to Wintrust, or made
available to Wintrust for its inspection from the books and records of the
Company or the Bank, true and complete copies of all Material Contracts.
"Material Contracts" include every contract, commitment, or arrangement, whether
written or oral (and the Company has delivered to


                                      A-8


Wintrust written descriptions of the terms and conditions of all oral Material
Contracts), of a material nature under which the Company or the Bank is
obligated on the date hereof, including the following:

                  (a) all consulting arrangements, and contracts for
         professional, advisory, and other services, including contracts under
         which the Company or the Bank performs services for others;

                  (b) all leases of real estate and personal property;

                  (c) all contracts, commitments and agreements for the
         acquisition, development or disposition of real or personal property
         other than conditional sales contracts and security agreements
         whereunder total future payments are, in each instance, less than
         $25,000;

                  (d) all contracts relating to the employment, engagement,
         compensation or termination of directors, officers, employees,
         consultants or agents of the Company or the Bank, and all pension,
         retirement, profit sharing, stock option, stock purchase, stock
         appreciation, insurance or similar plans or arrangements for the
         benefit of any employees, officers or directors of the Company,
         including all Benefit Plans as defined in Section 3.20;

                  (e) all loans, loan commitments, promissory notes, letters of
         credit or other financial accommodations or arrangements or evidences
         of indebtedness, including modifications, waivers or amendments
         thereof, extended to or for the benefit of the Company or the Bank;

                  (f) all loans, loan commitments, promissory notes, letters of
         credit or other financial accommodations or arrangements or evidences
         of indebtedness, including modifications, waivers or amendments
         thereof, extended to or for the benefit of any single borrower or
         related group of borrowers if the aggregate amount of all such loans,
         loan commitments, promissory notes, letters of credit or other
         financial accommodations or arrangements or evidences of indebtedness
         extended to such borrower or related group of borrowers exceeds
         $350,000;

                  (g) all union and other labor contracts;

                  (h) all agreements, contracts, mortgages, loans, deeds of
         trust, leases, commitments, indentures, notes, instruments and other
         arrangements which are with officers or directors of the Company or the
         Bank, any "affiliates" of the Company or the Bank within the meaning of
         Section 23A of the Federal Reserve Act or any record or beneficial
         owner of 5% or more of Company Common Stock, or any member of the
         immediate family or a related interest (as such terms are defined in 12
         C.F.R. ss.215.2(m)) of any such person, excepting any ordinary and
         customary loans and deposits that comply with applicable banking
         regulations;

                  (i) any contract involving total future payments by the
         Company or the Bank of more than $25,000 or which requires performance
         by the Company or the Bank beyond the second anniversary of the Closing
         Date, that by its terms does not terminate or is not terminable by the
         Company or the Bank without penalty within 30 days after the date of
         this Agreement;

                  (j) except for provisions of the articles of incorporation,
         articles of association and the by-laws of the Company or the Bank, all
         contracts under which the Company or the Bank has any obligation,
         direct, indirect, contingent or otherwise, to assume or guarantee any
         liability or to indemnify any person (other than in a fiduciary
         capacity);

                  (k) all joint venture or marketing agreements with any other
         person or entity; and

                  (l) all other material contracts, made other than in the usual
         or ordinary course of business of the Company or the Bank, to which the
         Company or the Bank is a party or under which the Company or the Bank
         is obligated.

         3.11 No Defaults. Each of the Company and the Bank has fulfilled and
taken all action reasonably necessary to date to enable it to fulfill, when due,
all of its material obligations under all Material Contracts to which it is a
party. There are no defaults by the Company or the Bank under any Material
Contract, and no events have occurred that, with the lapse of time or the
election of any other party, will become defaults by the Company or the Bank. To
the Company's knowledge, no breach or default by any other party under any
Material Contract has


                                      A-9



occurred or, is threatened that will or could impair the ability of the Company
or the Bank to enforce any of its rights under such Material Contract in any
material respect.

         3.12 Conflict of Interest Transactions. Except as set forth on the
Schedule of Interested Transactions, attached hereto as Schedule 3.12, no
principal officer or director of the Company or the Bank, or holder of 10% or
more of the Company Common Stock or any member of the immediate family or a
related interest (as such terms are defined in 12 C.F.R. ss.215.2(m)) of such
person: (a) has any material direct or indirect interest not otherwise disclosed
in this Agreement or the Schedules attached hereto in (i) any entity which does
business with the Company or the Bank or (ii) any property or asset which is
owned or used by the Company or the Bank in the conduct of its business; or (b)
has any financial, business or contractual relationship or arrangement with the
Company or the Bank, excluding any agreements and commitments entered into in
respect of the Bank's acceptance of deposits and investments or the making of
any loans, in each case in the Bank's ordinary course of business.

         3.13 Investments.

                  (a) Set forth on Schedule 3.13(a) is a complete and correct
         list and description as of May 31, 2003, of all investment and debt
         securities, mortgage-backed and related securities, marketable equity
         securities and securities purchased under agreements to resell that are
         owned by the Company or the Bank, other than in a fiduciary or agency
         capacity (the "Investment Securities"). The Company and the Bank each
         has good and marketable title to all Investment Securities held by it,
         free and clear of all Encumbrances, except for Permitted Encumbrances.
         The Investment Securities are valued on the books of the Company and
         the Bank in accordance with GAAP.

                  (b) Except as set forth on Schedule 3.13(b), and as may be
         imposed by applicable securities laws and the documents and instruments
         governing the terms of such securities, none of the Investment
         Securities is subject to any restriction, whether contractual or
         statutory, that materially impairs the ability of the Company or the
         Bank freely to dispose of such investment at any time. With respect to
         all material repurchase agreements to which the Company or the Bank is
         a party, the Company or the Bank, as the case may be, has a valid,
         perfected first lien or security interest in the securities or other
         collateral securing each such repurchase agreement, and the value of
         the collateral securing each such repurchase agreement equals or
         exceeds the amount of the debt secured by such collateral under such
         agreement.

                  (c) Except as set forth on Schedule 3.13(c), neither the
         Company nor the Bank has sold or otherwise disposed of any Investment
         Securities in a transaction in which the acquiror of such Investment
         Securities or other person has the right, either conditionally or
         absolutely, to require the Company or the Bank to repurchase or
         otherwise reacquire any such Investment Securities.

                  (d) There are no interest rate swaps, caps, floors, option
         agreements or other interest rate risk management arrangements to which
         the Company or the Bank is bound.

         3.14 Compliance with Laws; Legal Proceedings.

                  (a) The Company and the Bank are in compliance with all
         applicable federal, state, county and municipal laws and regulations
         (i) that regulate or are concerned in any way with the ownership and
         operation of banks or the business of banking or of acting as a
         fiduciary, including those laws and regulations relating to the
         investment of funds, the taking of deposits, the lending of money, the
         collection of interest, the extension of credit and the location and
         operation of banking facilities, or (ii) that otherwise relate to or
         affect the business or assets of the Company or the Bank or the assets
         owned, used, occupied or managed by either of them, except for such
         noncompliance which individually or in the aggregate would not have a
         Material Adverse Effect on the Company or the Bank. The Company and the
         Bank hold all material licenses, certificates, permits, franchises and
         rights from all appropriate federal, state or other Governmental
         Authorities necessary for the conduct of their businesses and the
         ownership of their assets.

                  (b) Except as set forth on Schedule 3.14(b), there are no
         claims, actions, suits or proceedings pending or, to the knowledge of
         the Company, threatened or contemplated against or affecting the
         Company or the Bank, at law or in equity, or before any federal, state
         or other Governmental Authority or any arbitrator or arbitration panel,
         whether by contract or otherwise, and there is no decree, judgment or
         order or supervisory


                                      A-10



agreement of any kind in existence against or restraining the Company or the
Bank from taking any action of any kind in connection with the business of the
Company or the Bank. Except as set forth on Schedule 3.14(b), neither the
Company nor the Bank has received from any federal, state or other Governmental
Authority any notice or threat (whether written or, to the knowledge of the
Company or the Bank, oral) of enforcement actions, or any criticism,
recommendation or suggestion of a material nature, and neither the Company nor
the Bank has any reasonable basis for believing that any such notice or threat,
criticism, recommendation or suggestion not otherwise disclosed herein is
contemplated, concerning capital, compliance with laws or regulations, safety or
soundness, fiduciary duties or other banking or business practices that has not
been resolved to the reasonable satisfaction of such Governmental Authority.

         3.15 Insurance. Attached as Schedule 3.15 is a Schedule of Insurance,
which sets forth a complete and correct list of all policies of insurance (a) in
which the Company or the Bank is named as an insured party, or (b) pursuant to
which the business, assets or properties of the Company or the Bank are insured,
and which are owned or carried by the Company or the Bank. The Company and the
Bank has in full force and effect policies of insurance issued by reputable
insurance companies against loss or damage of the kinds and in the amounts
identified in the policy summaries, and all premiums and costs with respect
thereto are set forth on Schedule 3.15. Neither the Company nor the Bank has
received notice (whether written or, to the knowledge of the Company, oral) from
any party of interest in or to any such policies claiming any breach or
violation of any provisions thereof, disclaiming or denying coverage thereof or
canceling or threatening cancellation of any such insurance contracts.

         3.16 Taxes. The Company and the Bank have each duly and timely filed
all federal, state and local income, franchise, excise, real and personal
property, employment, value-added and other material returns required to be
filed or delivered by the Company or the Bank (respectively) in connection with
the Company's or the Bank's business and operations (collectively, "Returns"),
all information included in such Returns is accurate in all material respects,
and all taxes required to be shown on such Returns as payable by the Company or
the Bank with respect to the income of the Company or the Bank have been paid
when due. Other than in connection with the federal and state income tax returns
related to tax year 2002, no application for an extension of time for filing any
Return or consent to any extension of the period of limitations applicable to
the assessment or collection of any tax is in effect with respect to the Company
or the Bank. Neither the Company nor the Bank is delinquent in the payment of
any taxes claimed to be due from the Company or the Bank by any taxing
authority, and adequate provisions for taxes (including any penalties and
interest) payable by the Company have been made on the books of the Company and
on the most recent of the Financial Statements. The Company has not received any
notice (whether written or, to the knowledge of the Company, oral) of any
proposed audit or proposed deficiency for any duty, tax, assessment or
governmental charge due from the Company with respect to the business and
operations of the Company, and there are no pending audits or claims with
respect thereto.

         3.17 Environmental Laws and Regulations.

                  (a) Except as set forth on Schedule 3.17, the Company and the
         Bank:

                           (i) have had and now have all environmental
                  approvals, consents, licenses, permits and orders required to
                  conduct the businesses in which they have been or are now
                  engaged;

                           (ii) have been and are in compliance in all material
                  respects with all applicable federal, state, county and
                  municipal laws, regulations, authorizations, licenses,
                  approvals, permits and orders relating to air, water, soil,
                  solid waste management, hazardous or toxic substances, or the
                  protection of health or the environment (collectively,
                  "Environmental Laws").

                  (b) Except as set forth on Schedule 3.17:

                           (i) there are no claims, actions, suits or
                  proceedings pending or, to the knowledge of the Company,
                  threatened or contemplated against, or involving, the Company
                  or the Bank or any assets of the Company or the Bank, under
                  any of the Environmental Laws (whether by reason of any
                  failure to comply with any of the Environmental Laws or
                  otherwise);

                           (ii) no decree, judgment or order of any kind under
                  any of the Environmental Laws has been entered against the
                  Company or the Bank;

                                      A-11



                           (iii) neither the Company nor the Bank:

                                    (1) is or was a generator or transporter of
                           hazardous waste, or the owner, operator, lessor,
                           sublessor, lessee or, to its knowledge, mortgagee of
                           a treatment, storage, or disposal facility or
                           underground storage tank as those terms are defined
                           under the Resource Conservation and
                           Recovery Act, as amended, or regulations promulgated
                           thereunder, or of real property on which such a
                           treatment, storage or disposal facility or
                           underground storage tank is or was located;

                                    (2) owns, operates, leases, subleases or to
                           its knowledge, holds a security interest in, or
                           owned, operated, leased or subleased (A) any facility
                           at which any Hazardous Substances (as defined below)
                           were treated, stored in significant quantities,
                           recycled, disposed or are or were installed or
                           incorporated or (B) any real property on which such a
                           facility is or was located;

                                    (3) arranged for the disposal or treatment,
                           arranged with a transporter for transport for
                           disposal or treatment of Hazardous Substances at any
                           facility from which there is a release or threat of
                           release, or accepts or accepted Hazardous Substances
                           for transport for disposal or treatment at any
                           facility, as those terms are defined under the
                           Comprehensive Environmental Response, Compensation
                           and Liability Act, as amended ("CERCLA"); or

                                    (4) is or was the holder of a security
                           interest where the party giving the security is or
                           was the owner or operator of a treatment, storage or
                           disposal facility, underground storage tank or any
                           facility at which any Hazardous Substances are or
                           were treated, stored in significant quantities,
                           recycled or disposed and where either the Company or
                           the Bank participates or participated in management
                           decisions concerning the facility's waste disposal
                           activities.

                  (c) To the Company's knowledge, there are no other facts,
         conditions or situations, whether now or heretofore existing, that
         could form the basis for any claim against, or result in any liability
         of, the Company or the Bank under any of the Environmental Laws.

                  (d) For purposes of this Section 3.18, "Hazardous Substance"
         shall mean a hazardous substance (as defined in CERCLA) and petroleum,
         including crude oil or any fraction thereof, but excluding underground
         crude oil in its natural unrefined state, prior to its initial
         extraction.

         3.18 Community Reinvestment Act Compliance. Neither the Company nor the
Bank has received any notice of non-compliance with the applicable provisions of
the Community Reinvestment Act ("CRA") and the regulations promulgated
thereunder, and the Company has never received a CRA rating of any kind from the
Office of the Comptroller of the Currency (the "OCC") or other applicable
Governmental Authority. The Company knows of no facts or circumstances, which
would cause either the Company or the Bank to fail to comply with such
provisions or to cause the Bank to receive a CRA rating of less than
satisfactory.


         3.19 Company Regulatory Reports. Since January 1, 2001, the Company and
the Bank have filed all reports, registrations and statements, together with any
amendments required to be made with respect thereto, required to be filed with
the Federal Reserve, the OCC and any other Governmental Authority or
self-regulatory organization with jurisdiction over any of the activities of the
Company or the Bank (the "Company Regulatory Reports"), and have paid all fees
and assessments due and payable in connection therewith. As of their respective
dates, the Company Regulatory Reports complied in all material respects with the
statutes, rules and regulations enforced or promulgated by the applicable
regulatory authority with which they were filed and did not contain any untrue
statement of a material fact or omit to state a material fact required to be
stated therein or necessary to make the statements therein, in light of the
circumstances under which they were made, not misleading.


         3.20 Employee Benefit Plans.

                  (a) Schedule 3.20 sets forth a complete and correct list of
         each employee benefit plan within the meaning of Section 3(3) of ERISA
         (the "ERISA Plans"), each compensation, consulting, employment or
         collective bargaining agreement, and each stock option, stock purchase,
         stock appreciation right, life, health,


                                      A-12


         disability or other insurance or benefit, bonus, deferred or incentive
         compensation, severance or separation, profit sharing, retirement, or
         other employee benefit plan, practice, policy or arrangement of any
         kind, oral or written, covering employees or former employees of the
         Company or the Bank which the Company or the Bank maintains or
         contributes to (or, with respect to any employee pension benefit plan
         (as defined in Section 3(2) of ERISA) has maintained or contributed to
         since the date of its incorporation) or to which the Company or the
         Bank is a party or by which it is otherwise bound (collectively,
         together with the ERISA Plans, the "Benefit Plans"). None of the
         Benefit Plans is a "defined benefit plan" (as defined in Section 414(j)
         of the Code). Neither the Company nor the Bank has, and has ever had,
         an affiliate that would be treated as a single employer together with
         the Company or the Bank (an "ERISA Affiliate") under Section 414 of the
         Code.

                  (b) Other than the employment agreement with the Bank's
         president, a true and complete copy of which has been provided to
         Wintrust, neither the Company nor the Bank has entered into or
         maintained any Benefit Plan which includes any change of control
         provisions which would cause an increase or acceleration of benefits or
         benefit entitlements to employees or former employees of the Company or
         the Bank or any other increase in the liabilities of the Company or the
         Bank under such Benefit Plan as a result of the transactions
         contemplated by this Agreement.

                  (c) Neither the Company nor the Bank maintains or
         participates, and has ever maintained or participated, in a
         multiemployer plan within the meaning of Section 3(37) of ERISA. None
         of the Company, the Bank, any director or employee of the Company or
         the Bank, or any fiduciary of any ERISA Plan has engaged in any
         transaction in violation of Section 406 or 407 of ERISA or any
         "prohibited transaction" (as defined in Section 4975(c)(1) of the Code)
         for which no exemption exists under Section 408(b) of ERISA or Section
         4975(d) of the Code in connection with such ERISA Plan. Neither the
         Company nor the Bank provides nor has ever provided medical benefits to
         former employees, except as required by Section 601 of ERISA.

                  (d) Each ERISA Plan that is intended to qualify under Section
         401 and related provisions of the Code is the subject of a
         determination letter from the Internal Revenue Service to the effect
         that it is so qualified under the Code and that its related funding
         instrument is tax exempt under Section 501 of the Code.

                  (e) Each Benefit Plan is, and since its inception, has been
         administered in material compliance with its terms and with all
         applicable laws, rules and regulations governing such Benefit Plan,
         including the rules and regulations promulgated by the Department of
         Labor, the Pension Benefit Guaranty Corporation and the Internal
         Revenue Service under ERISA, the Code or any other applicable law.
         Neither the Company nor any affiliate of the Company that is a
         fiduciary with respect to any Benefit Plan, has breached any of the
         responsibilities, obligations or duties imposed on it by ERISA.

                  (f) There is no litigation, claim or assessment pending or, to
         the Company's knowledge, threatened by, on behalf of, or against any of
         the Benefit Plans or against the administrators or trustees or other
         fiduciaries of any of the Benefit Plans that alleges a violation of
         applicable state or federal law. To the Company's knowledge, there is
         no reasonable basis for any such litigation, claim or assessment.

                  (g) No Benefit Plan fiduciary or any other person has, or has
         had, any liability to any Benefit Plan participant, beneficiary or any
         other person under any provisions of ERISA or any other applicable law
         by reason of any action or failure to act in connection with any
         Benefit Plan, including, but not limited to, any liability by any
         reason of any payment of, or failure to pay, benefits or any other
         amounts or by reason of any credit or failure to give credit for any
         benefits or rights.

                  (h) All accrued contributions and other payments to be made by
         the Company or the Bank to any Benefit Plan through the date hereof
         have been made or reserves adequate for such purposes have been set
         aside therefor and reflected in the Financial Statements. Neither the
         Company nor the Bank is in default in performing any of its contractual
         obligations under any of the Benefit Plans or any related trust
         agreement or insurance contract. There are no outstanding liabilities
         with respect to any Benefit Plan other than liabilities for benefits to
         be paid to participants in such Benefit Plan and their beneficiaries in
         accordance with the terms of such Benefit Plan.

                  (i) No Benefit Plan provides for payment of any amount which,
         considered in the aggregate with amounts payable pursuant to all other
         Benefit Plans, would exceed the amount deductible for federal income
         tax purposes by virtue of Section 280G or 162(m) of the Code.


                                      A-13



                  (j) There are no obligations or liabilities, whether
         outstanding or subject to future vesting, for any post-retirement
         benefits to be paid to participants under any of the Benefit Plans.

         3.21 Technology and Intellectual Property.

                  (a) Attached as Schedule 3.21 is a Schedule of Intellectual
         Property, which sets forth a complete and correct list of all (i)
         registered trademarks, service marks, copyrights and patents; (ii)
         applications for registration or grant of any of the foregoing; (iii)
         unregistered trademarks, service marks, trade names, logos and assumed
         names; and (iv) licenses for any of the foregoing, in each case, owned
         by the Company or the Bank or used in or necessary to conduct the
         Company's or the Bank's business as presently conducted. The items on
         Schedule 3.21, together with all other trademarks, service marks, trade
         names, logos, assumed names, patents, copyrights, trade secrets,
         computer software, licenses, formulae, customer lists or other
         databases, business application designs and inventions currently used
         in or necessary to conduct the business of the Company as presently
         conducted constitute the "Intellectual Property."

                  (b) Except as set forth on Schedule 3.21, the Company or the
         Bank has ownership of, or such other rights by license, lease or other
         agreement in and to, the Intellectual Property as is necessary to
         permit the Company and the Bank to use the Intellectual Property in the
         conduct of their respective businesses as presently conducted. Neither
         the Company nor the Bank has received notice (whether written or, to
         the knowledge of the Company or the Bank, oral) alleging that the
         Company or the Bank has infringed or violated any trademark, trade
         name, copyright, patent, trade secret right or other proprietary right
         of others, and to the Company's knowledge, it has not committed any
         such violation or infringement. Other than as set forth on Schedule
         3.21, to the Company's knowledge, there is no reason to believe that,
         upon consummation of the transactions contemplated hereby, the Company
         or the Bank will be in any way more restricted in its use of any of the
         Intellectual Property than it was on the date hereof under any contract
         to which the Company or the Bank is a party or by which it is bound, or
         that use of such Intellectual Property by the Company or the Bank will,
         as a result of such consummation, violate or infringe the rights of any
         person, or subject Wintrust, the Company or the Bank to liability of
         any kind, under any such contract.

         3.22 No Adverse Change. Other than as specifically disclosed in this
Agreement, the Financial Statements, or the Schedules delivered pursuant to this
Agreement, there has not occurred (a) since December 31, 2002 any Material
Adverse Effect on the Company or the Bank, or (b) any change or condition,
event, circumstance, fact or other occurrence, whether occurring before or since
December 31, 2002, that may reasonably be expected to have or result in a
Material Adverse Effect on the Company or the Bank. The Company knows of no
reason, based on the business or operations of the Company and the Bank, why the
Federal Reserve Application or any of the other regulatory approvals referenced
in Section 7.3 should be denied or unduly delayed.

         3.23 Conduct of Business in Normal Course. Since December 31, 2002, the
businesses of the Company and the Bank have been conducted only in the ordinary
and usual course consistent with past practice.

         3.24 Change in Business Relationships. As of the date of this
Agreement, neither the Company nor the Bank has received notice (whether written
or, to the knowledge of the Company or the Bank, oral), whether on account of
the transactions contemplated by this Agreement or otherwise, (a) that any
customer, agent, representative, supplier, vendor or business referral source of
the Company or the Bank intends to discontinue, diminish or change its
relationship with the Company or the Bank, that would have a Material Adverse
Effect on the Company, or (b) that any executive officer of the Company or the
Bank intends to terminate or substantially alter the terms of his or her
employment. There have been no complaints or disputes (in each case set forth in
writing) with any customer, agent, representative, supplier, vendor, business
referral source or other parties that have not been resolved which are
reasonably likely to have a Material Adverse Effect on the Company or the Bank.

         3.25 Brokers' and Finders' Fees. Neither the Company nor the Bank has
incurred any liability for brokerage commissions, finders' fees, or like
compensation with respect to the transactions contemplated by this Agreement.

         3.26 No Omissions. None of the representations and warranties contained
in Article III, in the Schedules provided for herein by the Company or in the
Financial Statements is false or misleading in any material


                                      A-14


respect or omits to state a fact herein or therein necessary to make such
statements not misleading in any material respect.

                                   ARTICLE IV
                         REPRESENTATIONS AND WARRANTIES
                       CONCERNING WINTRUST AND MERGER CO.

         Wintrust and Merger Co. hereby jointly and severally represent to the
Company as follows:

         4.1 Organization. Each of Wintrust and Merger Co. is a corporation duly
organized, validly existing and in good standing under the laws of the State of
Illinois, has the corporate power and authority to own its own properties and to
carry on its business as it is now being conducted, and is duly qualified and in
good standing as a foreign corporation in each jurisdiction where the location
and character of its properties and the business conducted by it require such
qualification, except where the failure to be so qualified would not have a
Material Adverse Effect on Wintrust or Merger Co.

         4.2 Capitalization. The authorized capital stock of Wintrust consists
of (i) 30,000,000 shares of common stock, no par value per share, of which
17,419,956 shares were issued and outstanding as of June 3, 2003, (ii)
20,000,000 shares of preferred stock, no par value per share, of which 100,000
shares are designated Junior Serial Preferred Stock A, no par value per share,
and no shares of preferred stock are issued and outstanding, and (iii) no shares
are held in treasury. As of June 3, 2003 there were (i) outstanding options in
respect of 2,921,437 shares of Wintrust Common Stock, (ii) outstanding warrants
for the purchase of 263,886 shares of Wintrust Common Stock, and (iii) preferred
share purchase rights outstanding pursuant to the Rights Agreement between
Wintrust and Illinois Stock Transfer Company, as Rights Agent, dated July 28,
1998. Such options, warrants and rights have been duly authorized by all
necessary corporate action (including shareholder approval, if necessary). Such
options and warrants have been validly executed, issued and delivered by
Wintrust, and constitute the legal, valid and binding obligations of Wintrust,
and are enforceable as to Wintrust in accordance with their terms. The shares of
Wintrust Common Stock to be issued upon exercise of such options and warrants
are validly authorized and, upon such exercise in accordance with their terms,
will be validly issued, fully paid, and nonassessable. The Wintrust Common Stock
is subject to certain preferences, qualifications, limitations, restrictions or
special or relative rights under Wintrust's articles of incorporation, a true
and complete copy of which has been previously provided to the Company. Except
for such options and warrants and preferred share purchase rights, there are no
options, agreements, contracts or other rights in existence to purchase or
acquire from Wintrust any shares of capital stock of Wintrust, whether now or
hereafter authorized or issued, other than shares issuable pursuant to employee
benefit or compensation plans referred to in the Wintrust SEC Documents.

         4.3 Authorization; No Violations. The execution and delivery of this
Agreement and the performance of Wintrust's and Merger Co.'s obligations
hereunder have been duly and validly authorized by each of the Boards of
Directors of Wintrust and Merger Co., do not violate or conflict with their
respective articles of incorporation or by-laws, the Illinois Act, or any
applicable law, court order or decree to which Wintrust or Merger Co. is a party
or subject, or by which Wintrust or Merger Co. or any of their respective
properties is bound, and require no further corporate or shareholder approvals
on the part of Wintrust and Merger Co. The execution and delivery of this
Agreement and the performance of Wintrust's and Merger Co.'s obligations
hereunder do not and will not result in any default or give rise to any right of
termination, cancellation or acceleration under any material note, bond,
mortgage, indenture or other agreement by which Wintrust or Merger Co. is bound.
This Agreement, when executed and delivered, will be a valid, binding and
enforceable obligation of each of Wintrust and Merger Co., subject to applicable
bankruptcy, insolvency, reorganization, moratorium or similar laws affecting
creditors generally and to general principles of equity.

         4.4 Consents and Approvals. No consents or approvals of, or filings or
registrations with, any Governmental Authority or with any third party are
necessary in connection with the execution and delivery by Wintrust or Merger
Co. of this Agreement and the consummation by Wintrust and Merger Co. of the
Merger except for (a) the filing by Wintrust of the Federal Reserve Application
with the Federal Reserve under the BHCA, (b) the filing with the Commission of
the Registration Statement (as defined in Section 5.4(a)), and (c) the filing of
the Articles of Merger with the Secretary of State of the State of Illinois
under the Illinois Act.


                                      A-15



         4.5 Wintrust SEC Documents and Financial Statements.

                  (a) Since January 1, 2000, Wintrust has timely filed all
         reports and other documents (including any amendments thereto) required
         to be filed with the Commission under the Securities Exchange Act of
         1934, as amended (the "Exchange Act") and the rules and regulations of
         the Commission (the "Wintrust SEC Documents"), and all such Wintrust
         SEC Documents have complied in all material respects, as of their
         respective filing dates and effective dates, as the case may be, with
         all applicable requirements of the Exchange Act. As of their respective
         filing dates, none of the Wintrust SEC Documents contained an untrue
         statement of a material fact or omitted to state a material fact
         required to be stated therein or necessary in order to make the
         statements therein, in light of the circumstances under which they were
         made, not misleading.

                  (b) The audited consolidated financial statements contained or
         incorporated by reference in Wintrust's Annual Report on Form 10-K for
         the years ended December 31, 2000, 2001 and 2002 and the unaudited
         interim financial statements included in Wintrust's most recent
         Quarterly Report on Form 10-Q have been prepared in conformity with
         GAAP applied on a consistent basis, and, together with the notes
         thereto, present fairly the consolidated financial position of Wintrust
         and its subsidiaries at the dates shown and the consolidated results of
         their operations, changes in stockholders' equity and cash flows for
         the periods then ended. The interim financial statements as of, and
         for, the periods ending after December 31, 2002 included in Wintrust's
         Quarterly Reports on Form 10-Q, as filed with the Commission, include
         all adjustments necessary for a fair presentation of the financial
         position of Wintrust and its subsidiaries and the results of their
         operations for the interim periods presented, subject to normal,
         recurring year-end adjustments and the omission of footnote disclosure.

                  (c) The reserves for possible loan losses shown on each of the
         balance sheets contained in the Wintrust SEC Documents are adequate
         under the requirements under GAAP to provide for possible losses, net
         of recoveries relating to loans previously charged off, on loans
         outstanding (including accrued interest receivable) as of the
         applicable date of such balance sheet. The aggregate consolidated loan
         balance of Wintrust as of March 31, 2003, in excess of such reserves
         shown on the balance sheet as of March 31, 2003, contained in the
         Wintrust SEC Documents is, to the knowledge of Wintrust, collectible in
         accordance with their terms.

                  (d) Except as disclosed in the Wintrust SEC Documents or as
         set forth on Schedule 4.5(d), neither Wintrust nor any banking
         subsidiary of Wintrust (a "Wintrust Bank") is a party to, and none of
         their respective properties or assets are bound by, any "material
         contract" required to be filed under Item 601(b)(10) of Regulation S-K
         of the Commission.

         4.6 Compliance with Laws; Legal Proceedings.

                  (a) Wintrust and its subsidiaries are each in compliance in
         all material respects with all applicable federal, state, county and
         municipal laws and regulations (i) that regulate or are concerned in
         any way with the ownership and operation of banks or the business of
         banking or of acting as a fiduciary, including those laws and
         regulations relating to the investment of funds, the taking of
         deposits, the lending of money, the collection of interest, the
         extension of credit and the location and operation of banking
         facilities, or (ii) that otherwise relate to or affect the business or
         assets of Wintrust or any of its subsidiaries or the assets owned,
         used, occupied or managed by Wintrust or any of its subsidiaries,
         except for such noncompliance which individually or in the aggregate
         would not have a Material Adverse Effect on Wintrust. Wintrust and its
         subsidiaries (direct and indirect) hold all material licenses,
         certificates, permits, franchises and rights from all appropriate
         federal, state or other Governmental Authorities necessary for the
         conduct of its business and the ownership of its assets.

                  (b) Except as may be disclosed in the Wintrust SEC Documents,
         there are no material claims, actions, suits or proceedings pending or,
         to the knowledge of Wintrust, threatened or contemplated against or
         affecting Wintrust or its subsidiaries, at law or in equity, or before
         any federal, state or other Governmental Authority or any arbitrator or
         arbitration panel, whether by contract or otherwise, and there is no
         decree, judgment or order or supervisory agreement of any kind in
         existence against or restraining Wintrust or its subsidiaries from
         taking any action of any kind in connection with their respective
         businesses. Except as may be disclosed in the Wintrust SEC Documents or
         as set forth on Schedule 4.6(b), none of Wintrust or its subsidiaries
         has received from any federal, state or other Governmental Authority
         any notice or threat (whether written or, to the knowledge of Wintrust,
         oral) of enforcement actions, or any criticism, recommendation or
         suggestion of a material nature, and none of Wintrust or its
         subsidiaries has any reasonable basis for believing that any such
         notice or threat, criticism,


                                      A-16



         recommendation or suggestion not otherwise disclosed herein is
         contemplated, concerning capital, compliance with laws or regulations,
         safety or soundness, fiduciary duties or other banking or business
         practices that has not been resolved to the reasonable satisfaction of
         such Governmental Authority.

         4.7 Wintrust Regulatory Reports. Since January 1, 2001, Wintrust and
its subsidiaries have filed all reports, registrations and statements, together
with any amendments required to be made with respect thereto, required to be
filed with the Federal Reserve, the OCC and any other Governmental Authority or
self-regulatory organization with jurisdiction over any of the activities of
Wintrust or its subsidiaries (the "Wintrust Regulatory Reports"), and have paid
all fees and assessments due and payable in connection therewith. As of their
respective dates, the Wintrust Regulatory Reports complied in all material
respects with the statutes, rules and regulations enforced or promulgated by the
applicable regulatory authority with which they were filed and did not contain
any untrue statement of a material fact or omit to state a material fact
required to be stated therein or necessary to make the statement therein, in
light of the circumstances under which they were made, not misleading.

         4.8 Taxes. Wintrust and each Wintrust Bank have each duly and timely
filed all state and federal income tax returns required to be filed or delivered
by Wintrust in connection with Wintrust's business and operations, and all
information included in such returns is accurate in all material respects, and
all state and federal taxes required to be shown on such returns as payable by
Wintrust with respect to the income of Wintrust have been paid when due. Other
than in connection with the federal and state income tax returns related to tax
year 2002, no application for an extension of time for filing any such income
tax return or consent to any extension of the period of limitations applicable
to the assessment or collection of any state or federal income tax is in effect
with respect to Wintrust. Wintrust has not received any notice (whether written
or, to the knowledge of Wintrust, oral) of any proposed audit or proposed
deficiency for any state or federal income tax, assessment or governmental
charge due from Wintrust with respect to the business and operations of
Wintrust, and there are no pending audits or claims with respect thereto


         4.9 Compliance with ERISA. All employee benefit plans (as defined in
Section 3(3) of ERISA) established or maintained by Wintrust or any Wintrust
Bank or to which Wintrust or any Wintrust Bank contributes, are in material
compliance with all applicable requirements of ERISA, and are in material
compliance with all applicable requirements (including qualification and
non-discrimination requirements in effect as of the Closing) of the Code for
obtaining the tax benefits the Code thereupon permits with respect to such
employee benefit plans. No such employee benefit plan has any amount of unfunded
benefit liabilities (as defined in Section 4001(a)(18) of ERISA) for which
Wintrust or any Wintrust Bank would be liable to any person or entity under
Title IV of ERISA if any such employee benefit plan were terminated as of the
Closing. Such employee benefit plans are funded in accordance with Section 412
of the Code (if applicable). There would be no obligations of Wintrust or any
Wintrust Bank under Title IV of ERISA relating to any such employee benefit plan
that is a multi-employer plan if any such plan were terminated or if Wintrust or
such Wintrust Bank withdrew from any such plan as of the Closing. All
contributions and premium payments due prior to the date hereof have been made,
and all contributions and premium payments due prior to Closing will be made by
Wintrust or a Wintrust Bank, as applicable, on a timely basis.


         4.10 No Defaults. Each of Wintrust and each Wintrust Bank has fulfilled
and taken all action reasonably necessary to date to enable it to fulfill, when
due, all of its material obligations under all material contracts identified or
required to be identified in the Wintrust SEC Documents. There are no defaults
under any such contract, and no events have occurred that, with the lapse of
time or the election of any other party, will become defaults by Wintrust or any
Wintrust Bank. To Wintrust's knowledge, no breach or default by any other party
under such contract has occurred or is threatened that will or could impair the
ability of Wintrust or any Wintrust Bank to enforce any of its rights under such
contract in any material respect.

         4.11 Compliance with Environmental Laws. Except as set forth on
Schedule 4.11, (a) there are no proceedings or orders against Wintrust or any
Wintrust Bank with respect to alleged violation of, or liability under,
Environmental Laws; (b) to the knowledge of Wintrust, there is no proceeding or
order threatened against Wintrust or any Wintrust Bank with respect to the
alleged violation of, or liability under, Environmental Laws; and (c) to the
knowledge of Wintrust, there are no facts, conditions or situations, whether now
or heretofore existing, that could form the basis for any claim against, or
result in any liability of, Wintrust.


                                      A-17



         4.12 Fiduciary Accounts. Each Wintrust Bank has properly administered
in all material respects all accounts for which it acts as fiduciary, including
accounts for which it serves as trustee, agent, custodian or investment
advisor, in accordance with the material terms of the governing documents and
applicable state and federal law and regulations.

         4.13 No Adverse Change. Except as disclosed in the Wintrust SEC
Documents, this Agreement, or the Schedules delivered pursuant to this
Agreement, there has not occurred (a) since December 31, 2002, any Material
Adverse Effect on Wintrust or any of its subsidiaries or (b) any change or
condition, event, circumstance, fact or other occurrence, whether occurring
before or since December 31, 2002, that may reasonably be expected to have or
result in a Material Adverse Effect on Wintrust. Wintrust knows of no reason,
based on the business or operations of Wintrust and its subsidiaries, why the
Federal Reserve Application or any of the other regulatory approvals referenced
in Section 7.3 or 8.3 would be denied or unduly delayed. The CRA rating of each
banking subsidiary of Wintrust is at least "satisfactory" or better.


         4.14 Brokers' and Finders' Fees. Except as set forth on Schedule 4.14,
neither Wintrust nor Merger Co. has incurred any liability for brokerage
commissions, finders' fees, or like compensation with respect to the
transactions contemplated by this Agreement.


         4.15 No Omissions. None of the representations and warranties contained
in Article IV or in the Schedules provided for herein is false or misleading in
any material respect or omits to state a fact herein necessary to make such
statements not misleading in any material respect.


                                    ARTICLE V
                            AGREEMENTS AND COVENANTS

         5.1 Conduct of Business. During the period commencing on the date
hereof and continuing until the Effective Time, the Company shall conduct the
Company's business and shall cause the Bank to conduct its business in the usual
and ordinary course consistent with prudent banking practice. Without limiting
the foregoing, without the prior written consent of Wintrust:

                  (a) no change shall be made in the articles of incorporation
         or by-laws of the Company or the charter or by-laws of the Bank;

                  (b) except with respect to the exercise of any Outstanding
         Company Option or Warrant, no change shall be made in the
         capitalization of the Company or the Bank or in the number of issued
         and outstanding shares of Company Common Stock or Warrants;

                  (c) the compensation of officers or key employees of the
         Company or the Bank shall not be increased, nor any bonuses paid;

                  (d) no Loans, or renewals or restructurings of Loans, in the
         amount of $500,000 or more (including Loans to any one borrower or
         related group of borrowers which, in the aggregate, equal or exceed
         $500,000) shall be made by the Bank except in the ordinary course of
         business and consistent with prudent banking practices and the Bank's
         current loan policies and applicable rules and regulations of
         applicable Governmental Authorities with respect to amount, term,
         security and quality of such borrower's or borrowers' credit;

                  (e) no dividends or other distributions shall be declared or
         paid by the Company or the Bank;

                  (f) the Company and the Bank shall each use their commercially
         reasonable efforts to maintain their present insurance coverage in
         respect to its properties and business;

                  (g) no significant changes shall be made in the general nature
         of the business conducted by the Company or the Bank;

                  (h) No action shall be taken in connection with the proposed
         "ISS Investment" further described on Schedule 5.1(h);


                                      A-18



                  (i) no employment, consulting or similar agreements shall be
         entered into by the Company or the Bank that are not terminable by the
         Company or the Bank on 30 days' or fewer notice without penalty or
         obligation;

                  (j) neither the Company nor the Bank shall take any action
         that would result in a termination, partial termination, curtailment,
         discontinuance of a Benefit Plan or merger of any Benefit Plan into
         another plan or trust;

                  (k) the Company and the Bank shall file all Returns in a
         timely manner and shall not make any application for or consent to any
         extension of time for filing any Return or any extension of the period
         of limitations applicable thereto;


                  (l) neither the Company nor the Bank shall make any
         expenditure for fixed assets in excess of $25,000 for any single item,
         or $100,000 in the aggregate, or shall enter into leases of fixed
         assets having an annual rental in excess of $25,000;


                  (m) neither the Company nor the Bank shall incur any
         liabilities or obligations, make any commitments or disbursements,
         acquire or dispose of any property or asset, make any contract or
         agreement, or engage in any transaction except in the ordinary course
         consistent with prudent banking practices and the Bank's current
         policies;

                  (n) neither the Company nor the Bank shall do or fail to do
         anything that will cause a breach by the Company or the Bank of, or
         default by the Company or the Bank under, any Material Contract;

                  (o) the Bank shall not engage or agree to engage in any
         "covered transaction" within the meaning of Sections 23A or 23B of the
         Federal Reserve Act (without regard to the applicability of any
         exemptions contained in Section 23A) or any transaction of the kind
         referred to in Section 3.12, unless the Bank has complied with all
         requirements of Sections 23A or 23B of the Federal Reserve Act;

                  (p) the Bank shall only purchase or invest in obligations of
         the government of the United States or agencies of the United States or
         state or local governments having maturities of not more than five
         years and which municipal obligations have been assigned a rating of A
         or better by Moody's Investors Service or by Standard & Poor's;

                  (q) no changes of a material nature shall be made in either
         the Company's or the Bank's accounting procedures, methods, policies or
         practices or the manner in which the Company or the Bank maintain their
         records; and

                  (r) the Bank shall not accept or renew any brokered deposits.

         5.2 Access to Information.

                  (a) Pending the Closing, representatives of Wintrust shall,
         during normal business hours and on reasonable advance notice to the
         Company, be given full access to the Company's and the Bank's records
         and business activities and be afforded the opportunity to observe
         their business activities and consult with their officers and employees
         regarding the same on an ongoing basis (without limiting the foregoing,
         to verify compliance by the Company with all terms of this Agreement);
         provided, however, that the foregoing actions do not interfere with the
         business operations of the Company and the Bank.

                  (b) Wintrust will use such information as is provided to it by
         the Company or the Bank or the representatives of either solely for the
         purpose of conducting business, legal and financial reviews of the
         Company and the Bank and for such other purposes as may be related to
         this Agreement, and Wintrust will, and will direct all of its agents,
         employees and advisors to, maintain the confidentiality of all such
         information in accordance with the terms of the letter agreement
         regarding confidentiality entered into by and between the Company and
         Wintrust dated April 16, 2003 (the "Confidentiality Agreement").

                  (c) Pending the Closing and solely for the purpose of
         permitting the Company to ascertain the correctness of the
         representations and warranties made in this Agreement by Wintrust to
         the Company,


                                      A-19



         representatives of the Company shall, during normal business hours and
         on reasonable advance notice to Wintrust, be given access to the
         records and business activities of Wintrust and the Wintrust Banks and
         be afforded the opportunity to observe their business activities and
         consult with their officers and employees regarding the same; provided,
         however, that in Wintrust's sole reasonable judgment the foregoing
         actions do not interfere with the business operations of Wintrust or
         any of its subsidiaries. The Company will, and will direct all of its
         agents, employees and advisors to, maintain the confidentiality of all
         such information in accordance with the terms of the Confidentiality
         Agreement.

         5.3 Meeting of Shareholders of the Company. As soon as practicable
after the date of this Agreement and the effectiveness of the Registration
Statement pursuant to Section 5.4, the Company shall call and hold a meeting of
its shareholders for the purpose of voting upon this Agreement, the Merger and
the transactions herein contemplated in accordance with the Company's articles
of incorporation, its by-laws and the Illinois Act (the "Shareholders Meeting").
The Company shall, through the Company Board, recommend to its shareholders,
consistent with its fiduciary duties, approval of this Agreement and the Merger.

         5.4 Registration Statement and Regulatory Filings.

                  (a) Wintrust shall file with the Commission within 45 days
         after the execution of this Agreement or as soon thereafter as
         practicable, a registration statement on an appropriate form under the
         Securities Act covering Wintrust Common Stock to be issued pursuant to
         this Agreement and shall use its reasonable best efforts to cause the
         same to become effective and thereafter, until the Effective Time or
         termination of this Agreement, to keep the same effective and, if
         necessary, amend and supplement the same. Such registration statement
         and any amendments and supplements thereto are referred to herein as
         the "Registration Statement." The Registration Statement shall include
         a Proxy Statement/Prospectus thereto reasonably acceptable to Wintrust
         and the Company, prepared by Wintrust and the Company for use in
         connection with the meeting of shareholders of the Company referred to
         in Section 5.3, all in accordance with the rules and regulations of the
         Commission. Wintrust shall, as soon as practicable after the execution
         of this Agreement, make all filings, if any, required to obtain all
         blue sky permits, authorizations, consents or approvals required for
         the issuance of Wintrust Common Stock. In advance of filing the
         Registration Statement, Wintrust shall provide the Company and its
         counsel with a copy of the Registration Statement and provide an
         opportunity to comment thereon, and thereafter shall promptly advise
         the Company and its counsel of any material communication received by
         Wintrust or its counsel from the Commission with respect to the
         Registration Statement. None of the information furnished by Wintrust
         or the Company for inclusion in the Registration Statement, the Proxy
         Statement/Prospectus or any other document filed with the Commission or
         any state securities commission, at the respective times at which such
         documents are filed with the Commission or such state securities
         commission, or, in the case of the Registration Statement, when it
         becomes effective, or in the case of the Proxy Statement/Prospectus,
         when mailed or at the time of the Shareholders Meeting, shall be false
         or misleading with respect to any material fact or shall omit to state
         any material fact necessary in order to make the statements therein, in
         light of the circumstances in which they were made, not misleading.

                  (b) Wintrust, within 30 days following execution and delivery
         of this Agreement, will file the Federal Reserve Application and take
         all other appropriate actions (except as otherwise specified in Section
         5.4(a) above) necessary to obtain the regulatory approvals referred to
         in Section 7.3 hereof, and the Company will use all reasonable and
         diligent efforts to assist in obtaining all such approvals. The
         obligation to take all appropriate actions shall not be construed as
         including an obligation to accept any terms of or conditions to a
         consent, authorization, order, or approval of, or any exemption by, any
         Governmental Authority or other party that are not acceptable to
         Wintrust, in its sole reasonable discretion, or to change the business
         practices of Wintrust or any of its subsidiaries in a manner not
         acceptable to Wintrust, in its sole reasonable discretion. In advance
         of filing any applications for such regulatory approvals, Wintrust
         shall provide the Company and its counsel with a copy of such
         applications (but excluding any information contained therein regarding
         Wintrust and its business or operations for which confidential
         treatment has been requested) and provide an opportunity to comment
         thereon, and thereafter shall promptly advise the Company and its
         counsel of any material communication received by Wintrust or its
         counsel from any regulatory authorities with respect to such
         applications.

         5.5 Listing of Shares. Wintrust shall use all reasonable and diligent
efforts to cause the shares of Wintrust Common Stock issuable in the Merger to
be approved for listing on the Nasdaq National Market.


                                      A-20


         5.6 Reasonable and Diligent Efforts. The Parties shall use reasonable
and diligent efforts in good faith to satisfy the various conditions to Closing
and to consummate the Merger as soon as practicable. None of the Parties
will intentionally take or intentionally permit to be taken any action that
would be in breach of the terms or provisions of this Agreement or that would
cause any of the representations contained herein to be or become untrue.

         5.7 Business Relations and Publicity. The Company shall use reasonable
and diligent efforts to preserve the reputation and relationship of the Company
and the Bank with suppliers, clients, customers, employees, and others having
business relations with the Company or the Bank. Wintrust and the Company shall
coordinate all publicity relating to the transactions contemplated by this
Agreement and, except as otherwise required by applicable law or the rules of
the Nasdaq National Market, or with respect to employee meetings, neither Party
shall issue any press release, publicity statement or other public notice
relating to this Agreement or any of the transactions contemplated hereby
without obtaining the prior consent of the other, which consent shall not be
unreasonably withheld, conditioned or delayed. The Company shall obtain the
prior consent (which shall not be unreasonably withheld, conditioned or delayed)
of Wintrust to the content of any communication to its shareholders. In
furtherance of the foregoing the Parties acknowledge that immediately after
execution of this Agreement Wintrust shall issue a news release (after
consultation with the Company as to its content) and file the same with the
Commission on Form 8-K.

         5.8 No Conduct Inconsistent with this Agreement.

                  (a) The Company shall not, and shall cause the Bank to not,
         during the term of this Agreement, directly or indirectly, solicit,
         encourage or facilitate inquiries or proposals or enter into any
         agreement with respect to, or initiate or participate in any
         negotiations or discussions with any person or entity concerning, any
         proposed transaction or series of transactions involving or affecting
         the Company or the Bank (or the securities or assets of either) that,
         if effected, would constitute an acquisition of control of either the
         Company or the Bank within the meaning of 12 U.S.C.A. ss.1817(j)
         (disregarding the exceptions set forth in 12 U.S.C.A. ss.1817(j)(17))
         and the regulations of the Federal


         Reserve thereunder (each, an "Acquisition Proposal"), or furnish any
         information to any person or entity proposing or seeking an Acquisition
         Proposal.

                  (b) Notwithstanding the foregoing, in the event that the
         Company Board determines in good faith and after consultation with
         outside counsel, that in light of a Superior Acquisition Proposal (as
         defined herein) it is necessary to pursue such Superior Acquisition
         Proposal in order to act in a manner consistent with such Board's
         fiduciary duties, the Company Board may, in response to an Acquisition
         Proposal which was not solicited by or on behalf of the Company or the
         Bank or which did not otherwise result from a breach of Section 5.8(a),
         subject to its compliance with Section 5.8(c), (i) furnish information
         with respect to the Company or the Bank to such person or entity making
         such Superior Acquisition Proposal pursuant to a customary
         confidentiality agreement that is no less restrictive than the
         confidentiality agreement entered into between the Company and
         Wintrust, (ii) participate in discussions or negotiations regarding
         such Superior Acquisition Proposal, (iii) withdraw, modify or otherwise
         change in a manner adverse to Wintrust, the Company's recommendation to
         its shareholders with respect to this Agreement and the Merger and/or
         (iv) terminate this Agreement in order to concurrently enter into an
         agreement with respect to such Superior Acquisition Proposal; provided,
         however, that the Company Board may not terminate this Agreement
         pursuant to this Section 5.8(b) unless and until (x) five (5) business
         days have elapsed following the delivery to Wintrust of a written
         notice of such determination by the Company Board and during such five
         (5) business day period, the Company and the Bank otherwise cooperate
         with Wintrust with the intent of enabling the Parties to engage in good
         faith negotiations so that the Merger and other transactions
         contemplated hereby may be effected and (y) at the end of such three
         business day period the Company Board continue reasonably to believe
         the Acquisition Proposal at issue constitutes a Superior Acquisition
         Proposal. A "Superior Acquisition Proposal" means any Acquisition
         Proposal containing terms which the Company Board determines in its
         good faith judgment (based on the advice of a financial advisor of
         nationally recognized reputation) to be more favorable to the Company's
         shareholders than the Merger and for which financing, to the extent
         required, is then committed or which, in the good faith judgment of the
         Company Board, is reasonably capable of being obtained by such third
         party.

                  (c) In addition to the obligations of the Company set forth in
         Section 5.8(a) and (b), the Company shall immediately advise Wintrust
         orally and in writing of any request for information or of any
         Acquisition Proposal, the material terms and conditions of such request
         or Acquisition Proposal and the identity of the person or entity making
         such request or Acquisition Proposal. The Company shall keep Wintrust
         reasonably


                                      A-21



         informed of the status and details (including amendments or proposed
         amendments) of any such request or Acquisition Proposal, including the
         status of any discussions or negotiations with respect to any Superior
         Acquisition Proposal.

         5.9 Pre-Closing Loan Review.

                  (a) The Company shall cause the Bank, prior to the Closing
         Date, to write off all Loans of the Bank that are required to be
         written off by the Bank's regulators or that, in conformity with past
         practices and policies of the Bank and GAAP, should be written off as
         Loan losses.

                  (b) The Company shall furnish Wintrust with full information
         regarding the status of each Loan contained in the Loan portfolio of
         the Bank, as of a date not more than 15 days prior to the Closing Date.


                  (c) Wintrust and the Company shall negotiate in good faith
         regarding the write-down, in conformity with the provisions of Section
         5.9(a) above, of potential Loan losses (net of reasonably conservative
         estimates of collateral recoveries and of applicable reserves)
         identified to the Company by Wintrust; provided, however, that (i) the
         Company shall not be required to take any actions as a result of such
         good faith negotiation (1) more than five (5) days prior to the Closing
         Date and (2) until such time as the Company shall have received
         reasonable assurances that all conditions precedent to Wintrust's
         obligations under this Agreement (except for the completion of actions
         to be taken at the Closing) have been satisfied, and (ii) any such
         actions taken as a result of such good faith negotiations shall not
         have any effect on the representations and warranties under Section 3.8
         made by the Company and the Bank as of the date of this Agreement.


         5.10 Board of Directors' Notices and Minutes. The Company shall give
reasonable notice to Wintrust of all meetings of the Company Board and any of
its committees, and the board of directors of the Bank and any of its
committees, and if known, the agenda for or business to be discussed at such
meeting. To the extent permissible under law, the Company shall promptly
transmit to Wintrust copies of all notices, minutes, consents and other
materials that the Company or the Bank provides to their directors, other than
materials relating to any proposed acquisition of the Company or the Bank or
this Agreement or the Merger, subject to the Company's compliance with Section
5.8. Wintrust agrees to hold in confidence and trust and to act in a fiduciary
manner with respect to all such information.

         5.11 Untrue Representations and Warranties. During the term of this
Agreement, if any Party becomes aware of any facts or of the occurrence or
impending occurrence of any event that would cause one or more of such Party's
representations and warranties contained in this Agreement to be or to become
untrue as of the Closing Date then:

                  (a) such Party shall immediately give detailed written notice
         thereof to the other Parties; and

                  (b) such Party shall use reasonable and diligent efforts to
         change such facts or events to make such representations and warranties
         true, unless the same shall have been waived in writing by the other
         Parties.

         5.12 Director and Officer Liability Coverage. Wintrust agrees to
provide each of the directors and officers of the Company and the Bank after the
Effective Time substantially the same coverage against personal liability for
actions taken after the Effective Time as is provided to directors and officers
of Wintrust. Such coverage may be provided through an insurance policy or
through an agreement by Wintrust to indemnify such directors and officers.
Wintrust further agrees to cause the Surviving Corporation for a period of five
years after the Effective Time to indemnify the current and past directors and
officers of the Company and the Bank for all actions taken by them prior to the
Effective Time in their respective capacities as directors and officers of the
Company and the Bank to the same extent as the indemnification provided by the
Company and the Bank to such directors and officers immediately prior to the
Effective Time.

         5.13 Interim Financial Statements. Prior to the Closing Date, the
Company shall deliver to Wintrust interim financial statements of the Company as
of the end of each month as promptly as practicable after they become available.
Such interim financial statements shall be prepared in conformity in all
material respects with GAAP applied on a basis consistent with the Financial
Statements.


                                      A-22



         5.14 Dissent Process. The Company will give to Wintrust prompt notice
of any written notice relating to the exercise of dissenters' rights granted
under the Illinois Act, including the name of the dissenting stockholder and the
number of shares of Company Common Stock to which the dissent relates. Wintrust
will have the right to participate in all negotiations and proceedings relating
thereto, and exceptions required by law. The Company will not make any payment
with respect to, or settle or offer to settle, any appraisal demands without
Wintrust's prior written consent.

         5.15 Section 368(a) Reorganization. Either prior to or after the
Closing Date, none of the Parties shall take or cause to be taken any action, or
omit to take any action or cause any omission, which would cause the Merger not
to qualify as a reorganization under Section 368(a) of the Code.

         5.16 Exercise of Warrants and Options. Notwithstanding anything
contained in this Agreement to the contrary, Wintrust and the Company each
acknowledge and agree that the holder of any Warrant or Outstanding Company
Option may, at any time prior to the commencement of the ten trading-day period
during which the Exchange Ratio is determined, exercise such Warrant or
Outstanding Company Option in accordance with its terms and conditions.

         5.17 Converted Options. Wintrust agrees to assume and honor each of the
Converted Options in accordance with their terms. Within 30 days after the
Closing Date, Wintrust shall file a registration statement with the Commission
with respect to the shares of Wintrust Common Stock to be covered by such
Converted Options. Such shares of Wintrust Common Stock shall be duly authorized
and, upon exercise of such Converted Options, shall be validly issued, fully
paid and nonassessable, and not in violation of or subject to any preemptive
rights except as set forth in Wintrust's articles of incorporation. Wintrust
shall after the Effective Time have reserved sufficient shares of Wintrust
Common Stock for issuance with respect to such options.

         5.18 TM Acceptance Corp. Lease Financing Portfolio. The Bank has
entered into that certain Program Agreement dated as of June 22, 2001 by and
among the Bank, TM Acceptance Corp., as Lessor thereunder, and Toshiba Machine
Company, America, as Vendor thereunder (the "Program Agreement"), pursuant to
which Lessor has and may continue to offer to sell to the Bank, and the Bank has
and may continue to purchase from Lessor, Leases regarding the sale or financing
by Lessor of Equipment to certain Lessees (as such terms are defined in the
Program Agreement, and which are used in this Section 5.18). In connection with
the Program Agreement, the Company shall:

                  (a) within 45 days of the date of this Agreement, certify in
         writing and demonstrate to the reasonable satisfaction of Wintrust
         that:

                           (i) the Lessor has perfected first priority security
                  interests in all Equipment that is the subject of all Leases;

                           (ii) the Lessor has executed and delivered to the
                  Bank an Assignment (as such term is defined in the Program
                  Agreement) for each of the Leases;

                           (iii) each Lease is covered by adequate insurance,
                  evidenced by insurance policy certificates naming Lessor as
                  loss payee, and Lessor has assigned all of its rights as loss
                  payee under such policies to the Bank; and

                           (iv) the Bank and Lessor have established the Lock
                  box as required under Article IV of the Program Agreement, and
                  as of the expiration of such 45-day period all Payments (as
                  defined in the Program Agreement) are being directed and
                  delivered to the Lock box and no such Payments are being
                  directed or delivered to Lessor; and

                  (b) as of the Closing Date, cause there to be no Payment
         obligations under any Lease greater than 30 days past due.

                                      A-23



                                   ARTICLE VI
                            EMPLOYEE BENEFIT MATTERS

         6.1 Benefit Plans. Schedule 6.1 lists all of the employees of the
Company and the Bank (the "Employees"). Wintrust and the Company Board shall
together review the Benefit Plans and the coverages provided thereunder.
Effective as of the Closing Date, (i) the Company Board shall cause the Company
to terminate all Benefit Plans other than the Company's 401(k) plan, health,
dental, life and disability insurance plans, and long-term care plan
(the "Retained Plans"), and to pay prior to the Closing or accrue fully any
liabilities under the Benefit Plans (including the Retained Plans ) or arising
out of such termination of Benefit Plans, and (ii) each full-time Employee shall
become eligible for and entitled to participate in Wintrust's benefit plans
(other than its benefit plans that are similar to the Retained Plans) on the
same terms and subject to the same conditions as all other U.S. employees of
Wintrust and its subsidiaries. From and after the Closing Date Wintrust shall
continue coverage for the Employees under the Company's Retained Plans in effect
prior to the Closing Date, to the extent not in violation of any statute, law
(including common law), ordinance, rule or regulation applicable to such plans
or the qualifications or requirements of such plans, until such time as Wintrust
determines such plans are to be terminated or merged with existing Wintrust
plans, at which time all Employees previously covered under such Retained Plans
shall become eligible for and entitled to participate in Wintrust's similar
plans on the same terms and subject to the same conditions as all other U.S.
employees of Wintrust and its subsidiaries. To the extent permitted by
applicable law the Company shall notify Wintrust on the Closing Date of the
existence or absence of any significant pre-existing conditions of any insureds
under the Benefit Plans. Wintrust shall use its reasonable and diligent efforts
to cause any pre-existing condition limitations under Wintrust's medical benefit
plans to be waived. For purposes of determining eligibility to participate and,
where applicable, vesting under Wintrust's applicable retirement savings plan
and employee stock purchase plan, Wintrust's short-term disability plans and
vacation policy, each Employee shall receive past service credit for his or her
prior employment with the Company as if such Employee had then been employed by
Wintrust. Credited service under Wintrust's retirement savings plan will
commence as of the date an Employee commences participation in Wintrust's
benefit plans. Wintrust reserves the right to change or terminate its employee
benefit plans at any time.

         6.2 No Rights or Remedies. Nothing in this Article shall confer upon
any Employee or his or her legal representative, any rights or remedies,
including any right to employment, or continued employment, for any specified
period, or any nature or kind whatsoever under or by reason of this Agreement.


                                   ARTICLE VII
                             CONDITIONS PRECEDENT TO
                     OBLIGATIONS OF WINTRUST AND MERGER CO.

         Unless the conditions are waived by Wintrust, all obligations of
Wintrust and Merger Co. under this Agreement are subject to the fulfillment, on
or before the Closing, of each of the following conditions:

         7.1 Representations and Warranties; Performance of Agreements. Each of
the representations and warranties contained in Article III of this Agreement
that are qualified by materiality shall be true and correct in all respects as
of the Closing Date, and each of the representations and warranties contained in
Article III that are not qualified by materiality shall be true and correct in
all material respects, except to the extent such representations and warranties
speak as of an earlier date, they shall be tested as of such earlier date. The
Company shall have performed in all material respects all agreements herein
required to be performed by Sellers and the Company on or before the Closing.

         7.2 Closing Certificate. Wintrust shall have received a certificate of
the Company signed by a senior executive officer of the Company, dated as of the
Closing Date, certifying in such detail as Wintrust may reasonably request, as
to the fulfillment of the conditions to the obligations of Wintrust set forth in
this Agreement that are required to be fulfilled by the Company on or before the
Closing.

         7.3 Regulatory and Other Approvals. Wintrust shall have obtained the
approval of all appropriate regulatory entities of the transactions contemplated
by this Agreement and the Merger, all required regulatory waiting periods shall
have expired, and there shall be pending on the Closing Date no motion for
rehearing or appeal


                                      A-24



from such approval or any suit or action seeking to enjoin the Merger or to
obtain substantial damages in respect of such transaction.

         7.4 Approval of Merger and Delivery of Agreement. This Agreement and
the Merger shall have been approved by the shareholders of the Company in
accordance with the Company's articles of incorporation, by-laws and the
Illinois Act, and the proper officers of the Company shall have executed and
delivered to Wintrust copies of this Agreement and the Articles of Merger, in
form suitable for filing with the Secretary of State of the State of Illinois,
and shall have executed and delivered all such other certificates, statements or
instruments as may be necessary or appropriate to effect such a filing. The
holders of not more than 5% of the shares of Company Common Stock shall have
given written demand for dissenter's rights in accordance with the Illinois Act.

         7.5 Effectiveness of the Registration Statement. The Registration
Statement shall have become effective with respect to the shares of Wintrust
Common Stock to be issued in the Merger, no stop order suspending the
effectiveness of such Registration Statement shall have been issued and no
material proceeding for that purpose shall have been instituted or threatened in
writing.

         7.6 No Litigation. No suit or other action shall have been instituted
or threatened in writing seeking to enjoin the consummation of the Merger or to
obtain other relief in connection with this Agreement or the transactions
contemplated herein that Wintrust believes, in good faith and with the written
advice of outside counsel, makes it undesirable or inadvisable to consummate the
Merger by reason of the probability that the proceeding would result in the
issuance of an order enjoining the Merger or in a determination that the Company
or the Bank has failed to comply with applicable legal requirements of a
material nature in connection with the Merger or actions preparatory thereto or
would have a Material Adverse Effect on the Company or the Bank.

         7.7 Environmental Surveys. Wintrust shall have received from the
Company copies of reports of Phase I environmental audits of all real property
or facilities used by either the Company or the Bank in the conduct of its
business, conducted by an independent environmental consultant reasonably
acceptable to Wintrust. Wintrust shall pay the costs of obtaining such Phase I
environmental audits. No such environmental audit shall have identified any
violation of the Environmental Laws or condition relating to the environment,
human health or safety which could reasonably be expected to have a Material
Adverse Effect on the Company or the Bank.

         7.8 Opinion of Counsel. Wintrust shall have received the opinion of
Barack, Ferrazzano, Kirschbaum, Perlman & Nagelberg LLC, counsel for the
Company, dated as of the Closing Date, and in form substantially similar to
Exhibit C and reasonably satisfactory to Wintrust and its counsel.

         7.9 Employment Agreements. At least one of those three persons
identified on Schedule 7.9, who as of the date of this Agreement are either
under an employment agreement with the Company or have entered into an
employment agreement with Merger Co. in the form attached as Exhibit D to be
effective as of the Effective Time, shall be an employee in good standing with
the Company or the Bank as of the Closing Date and capable of performing his
duties under his employment agreements as of the Effective Time.

         7.10 No Adverse Changes. Between the date of this Agreement and the
Closing Date, the business of the Company and the Bank, taken as a whole, shall
have been conducted in the ordinary course, in all respects consistent with
prudent banking practices, and there shall not have occurred any change or any
condition, event, circumstance, fact or occurrence, other than as provided in
this Agreement, that would have a Material Adverse Effect on the Company.

         7.11 Minimum Net Worth and Loan Loss Reserve Requirements. As of the
last day of the month preceding the Closing Date: (a) the shareholders' equity
in the Company, determined in conformity with GAAP applied on a basis consistent
with the preparation of the Financial Statements, shall be at not less than
$9,400,000, provided, however, that for purposes of this Section 7.11(a) only,
the Company's shareholders' equity (i) shall be increased by any fees for
professional services actually incurred by the Company in connection with this
Agreement and the transactions contemplated herein, up to a maximum of $150,000,
and (ii) shall not take into account any additions of shareholders' equity in
excess of a maximum of $100,000 that may result from the exercise by any
shareholders of any Outstanding Company Options or Warrants; and (b) the Bank's
reserve for loan losses, determined as described in Section 3.8, shall be not
less than 1.10% of the Bank's net Loans (gross Loans less unearned discounts).


                                      A-25


         7.12 Voting Agreements. On or before July 9, 2003, Wintrust shall have
received a Voting Agreement, in the form attached hereto as Exhibit E, executed
by each of those shareholders of the Company identified on Schedule 7.12, each
of whom is an officer or director of the Company or the Bank.

         7.13 TM Acceptance Corp. Lease Financing Portfolio. The Company and the
Bank shall have fully complied with the provisions of Section 5.18.

         7.14 Consents. The Company shall have obtained or caused to be obtained
(a) all written consents under those Material Contracts as set forth on Schedule
3.5, and (b) all other written consents, permissions and approvals as required
under any other agreements, contracts, appointments, indentures, plans, trusts
or other arrangements with third parties required to effect the transactions
contemplated by this Agreement where the failure to obtain such consents,
permissions and approvals would have a Material Adverse Effect on the Company or
Wintrust's rights under this Agreement.

         7.15 Other Documents. Wintrust shall have received at the Closing such
other customary documents, certificates, or instruments as they may have
reasonably requested evidencing compliance by the Company with the terms and
conditions of this Agreement.


                                  ARTICLE VIII
                       CONDITIONS PRECEDENT TO OBLIGATIONS
                                 OF THE COMPANY

         Unless the conditions are waived by the Company, all obligations of the
Company under this Agreement are subject to the fulfillment, on or before the
Closing, of each of the following conditions:

         8.1 Representations and Warranties; Performance of Agreements. Each of
the representations and warranties contained in Article IV of this Agreement
that are qualified by materiality shall be true and correct in all respects as
of the Closing Date, and each of the representations and warranties contained in
Article IV that are not qualified by materiality shall be true and correct in
all material respects, except to the extent such representations and warranties
speak as of an earlier date, they shall be tested as of such earlier date.
Wintrust and Merger Co. shall have performed in all material respects all
agreements herein required to be performed by Wintrust and Merger Co. on or
before the Closing.

         8.2 Closing Certificates. The Company shall have received certificates
signed by the Chief Executive Officer, a Senior Executive Vice President, an
Executive Vice President, or a Senior Vice President of each of Wintrust and
Merger Co. dated as of the Closing Date, certifying in such detail as the
Company may reasonably request, as to the fulfillment of the conditions to the
obligations of the Company as set forth in this Agreement.

         8.3 Regulatory and Other Approvals. Wintrust shall have obtained the
approval of all appropriate regulatory entities of the transactions contemplated
by this Agreement and the Merger, all required regulatory waiting periods shall
have expired, and there shall be pending on the Closing Date no motion for
rehearing or appeal from such approval or any suit or action seeking to enjoin
the Merger or to obtain substantial damages in respect of such transaction.

         8.4 Delivery of Agreement. The proper officers of Wintrust and Merger
Co. shall have executed and delivered to the Company copies of this Agreement
and the Articles of Merger, in form suitable for filing with the Secretary of
State of the State of Illinois, and shall have executed and delivered all such
other certificates, statements or instruments as may be necessary or appropriate
to effect such a filing.

         8.5 Effectiveness of the Registration Statement. The Registration
Statement shall have become effective with respect to the shares of Wintrust
Common Stock to be issued in the Merger, no stop order suspending the
effectiveness of such Registration Statement shall have been issued and no
material proceeding for that purpose shall have been instituted or threatened in
writing.

         8.6 No Litigation. No suit or other action shall have been instituted
or threatened in writing seeking to enjoin the consummation of the Merger or to
obtain other relief in connection with this Agreement or the


                                      A-26



transactions contemplated herein that the Company believes, in good faith and
with the written advice of outside counsel, makes it undesirable or inadvisable
to consummate the Merger by reason of the probability that the proceeding would
result in the issuance of an order enjoining the Merger or in a determination
that Wintrust or Merger Co. has failed to comply with applicable legal
requirements of a material nature in connection with the Merger or actions
preparatory thereto or would have a Material Adverse Effect on Wintrust.

         8.7 Opinions of Counsel.

                  (a) The Company shall have received the opinion of Schiff
         Hardin & Waite, counsel for Wintrust and Merger Co., dated as of the
         Closing Date, and in form substantially similar to Exhibit F and
         reasonably satisfactory to the Company and its counsel.

                  (b) The Company shall have received the opinion of Barack,
         Ferrazzano, Kirschbaum, Perlman & Nagelberg LLC, counsel to the
         Company, dated as of the Closing Date, to the effect that the Merger
         will constitute a "reorganization" within the meaning of Section 368(a)
         of the Code, and that the Company and Wintrust will each be a party to
         such reorganization within the meaning of Section 368(a) of the Code.
         The tax opinion shall be supported by one or more fact certificates or
         affidavits from Wintrust or Merger Co., in such form and content as may
         reasonably be requested by counsel to the Company.

         8.8 No Adverse Changes. Between the date of this Agreement and the
Closing Date, there shall not have occurred any change or any condition, event,
circumstance, fact or occurrence, other than as provided in this Agreement, that
would have a Material Adverse Effect on Wintrust.

         8.9 Nasdaq Listing. The Wintrust Common Stock to be issued to holders
of Company Common Stock pursuant to the Merger shall have been approved for
listing on the Nasdaq National Market, subject to official notice of issuance if
required.

         8.10 Other Documents. The Company shall have received at the Closing
all such other customary documents, certificates, or instruments as they may
have reasonably requested evidencing compliance by Wintrust and Merger Co. with
the terms and conditions of this Agreement.


                                   ARTICLE IX
            NON-SURVIVAL OF REPRESENTATIONS, WARRANTIES AND COVENANTS

         9.1 Non-Survival. None of the representations, warranties, covenants
and agreements in this Agreement shall survive the Effective Time, except for
those covenants or agreements contained herein which by their terms apply in
whole or in part after the Effective Time. Without limiting the foregoing, none
of the directors or officers of the Parties shall have any liability for any of
the representations, warranties, covenants and agreements contained herein.


                                    ARTICLE X
                                     GENERAL

         10.1 Expenses. Except as otherwise provided in this Section 10.1, all
costs and expenses incurred in the consummation of this transaction, including
any brokers' or finders' fees, shall be paid by the Party incurring such cost or
expense.

                  (a) Each of Wintrust and the Company shall bear and pay
         one-half of the costs and expenses incurred in connection with the
         filing, printing and mailing of the Registration Statement, including
         filing fees to the Commission but excluding legal and accounting fees
         related thereto.

                  (b) In the event that this Agreement is terminated by Wintrust
         because the Company or the Bank committed a material breach of its
         material obligations under this Agreement, unless such breach is a
         result of the failure by Wintrust to perform and comply in all material
         respects with any of its material obligations under this Agreement
         which are to be performed or complied with by it prior to or on the
         date of such termination, then,


                                      A-27


         provided Wintrust is in material compliance with all of its material
         obligations under this Agreement, the Company shall reimburse Wintrust
         in an amount, not to exceed $150,000, for the out-of-pocket expenses
         and costs, subject to verification thereof, that Wintrust (i) has
         incurred in furtherance of this Agreement and the transactions
         contemplated herein and (ii) is reasonably expected to incur as a
         result of the Company's breach of this Agreement, including, but not
         limited to, reasonable fees of professionals engaged for such purpose
         by or on behalf of Wintrust; provided, however, that except as provided
         in Section 10.1(c), such sums shall constitute liquidated damages and
         the receipt thereof shall be Wintrust's sole and exclusive remedy under
         this Agreement. Notwithstanding the foregoing, if this Agreement is
         terminated by Wintrust as a result of the Company's willful breach of
         this Agreement, then in addition to recovery of its out-of-pocket
         expenses and costs, Wintrust shall be entitled to recover such other
         amounts as it may be entitled to receive at law or in equity.

                  (c) In the event that this Agreement is terminated (i) by
         Wintrust as a result of a breach by the Company of its covenant in
         Section 5.8(a), (ii) by the Company pursuant to Section 10.2(e), or
         (iii) pursuant to Sections 10.2(a) or 10.2(b) and within six months
         after the date of such termination the Company or the Bank has either
         consummated or entered into a definitive agreement relating to an
         Acquisition Proposal which was made known to any member of the Company
         Board and not disclosed to Wintrust prior to the date of such
         termination, then the Company shall pay to Wintrust a termination fee
         equal to $1,000,000.

                  (d) In the event that this Agreement is terminated by the
         Company because Wintrust committed a material breach of its material
         obligations under this Agreement, unless such breach is a result of the
         failure by the Company or the Bank to perform and comply in all
         material respects with any of its material obligations under this
         Agreement which are to be performed or complied with by it prior to or
         on the date of such termination, then, provided the Company and the
         Bank are each in material compliance with all of its material
         obligations under this Agreement, Wintrust shall reimburse the Company
         in an amount, not to exceed $150,000, for the out-of-pocket expenses,
         subject to verification thereof, that the Company (i) has incurred in
         furtherance of this Agreement and the transactions contemplated herein
         and (ii) is reasonably expected to incur as a result of Wintrust's
         breach of this Agreement, including, but not limited to, reasonable
         fees of professionals engaged for such purpose by or on behalf of the
         Company; provided, however, that such sums shall constitute liquidated
         damages and the receipt thereof shall be the Company's sole and
         exclusive remedy under this Agreement. Notwithstanding the foregoing,
         if this Agreement is terminated by the Company as a result of
         Wintrust's willful breach of this Agreement, then in addition to
         recovery of its out-of-pocket expenses and costs, the Company shall be
         entitled to recover such other amounts as it may be entitled to receive
         at law or in equity.

                  (e) In the event this Agreement is terminated pursuant to
         Section 10.2(b) because Wintrust fails to obtain all of the necessary
         regulatory approvals described in Sections 7.3 and 8.3 for any reason
         other than regulatory matters relating solely to the Company or the
         Bank, Wintrust shall pay to the Company $150,000, provided, however,
         that such sums shall constitute liquidated damages and the receipt
         thereof shall be the Company's sole and exclusive remedy under this
         Agreement.

                  (f) In the event this Agreement is terminated pursuant to
         Section 10.2(b) because Wintrust fails to obtain all of the necessary
         regulatory approvals described in Sections 7.3 and 8.3 because of
         regulatory matters relating solely to the Company or the Bank, the
         Company shall pay to Wintrust $150,000, provided, however, that except
         as provided in Section 10.1(c), such sums shall constitute liquidated
         damages and the receipt thereof shall be Wintrust's sole and exclusive
         remedy under this Agreement.

                  (g) In the event this Agreement is terminated pursuant to
         either Section 10.2(a) or Section 10.2(b) for reasons other than as
         contemplated by subsections (e) and (f) above, Wintrust shall pay to
         the Company $25,000, which amount is intended to compensate the Company
         for its out-of-pocket expenses and time and effort in connection with
         the Agreement, provided, however, that such sums shall constitute
         liquidated damages and the receipt thereof shall be the Company's sole
         and exclusive remedy under this Agreement.

All costs and expenses reasonably estimated to have been incurred by the Company
shall be either paid or accrued for on or prior to the Closing Date; provided,
however, that nothing in this Section 10.1 shall be deemed to relieve the
Company of its liability to pay any expenses incurred in connection with this
Agreement following the Closing.


                                      A-28


         10.2 Termination. This Agreement may be terminated:

                  (a) at any time by written agreement between Wintrust and the
         Company;

                  (b) by either Wintrust or the Company if the Closing has not
         occurred (other than through the failure of any Party seeking to
         terminate this Agreement to comply fully with its obligations under
         this Agreement) by December 31, 2003, or such later date agreed to by
         the Parties, provided, however, that such termination date shall
         automatically be extended until March 31, 2004, if the sole impediment
         to Closing is a delay in either (i) the determination of the
         effectiveness of the Registration Statement or (ii) the Federal
         Reserve's approval of the Federal Reserve Application;

                  (c) by Wintrust by written notice to the Company, if (i) any
         of the conditions in Article VII has not been satisfied as of the
         Closing Date or if satisfaction of such a condition is or becomes
         impossible (other than through the failure of Wintrust to comply with
         its obligations under this Agreement); and (ii) Wintrust has not waived
         such condition on or before the Closing Date;

                  (d) by the Company by written notice to Wintrust, if (i) any
         of the conditions in Article VIII has not been satisfied as of the
         Closing Date or if satisfaction of such a condition is or becomes
         impossible (other than through the failure of the Company or the Bank
         to comply with its obligations under this Agreement); and (ii) the
         Company has not waived such condition on or before the Closing Date; or

                  (e) by the Company, if pursuant to Section 5.8(b) the Company
         Board determines that its fiduciary duties require it to accept an
         unsolicited Acquisition Proposal from a third party, or by Wintrust if
         an Acquisition Proposal from a third party is accepted by the Company
         or consummated, in each case by written notice to the other party.

Any termination of this Agreement shall not affect any rights accrued prior to
such termination.

         10.3 Confidential Information. Wintrust, Merger Co. and the Company
each covenant that, in the event the transactions contemplated by this Agreement
are not consummated, each such Party will keep in strict confidence and return
all documents containing any information concerning the properties, business,
and assets of the other Parties that may have been obtained in the course of
negotiations or examination of the affairs of each other Party either prior or
subsequent to the execution of this Agreement (other than such information as
shall be in the public domain or otherwise ascertainable from public or outside
sources), except to the extent that disclosure is required by judicial process
or governmental or regulatory authorities.

         10.4 Non-Assignment. Neither this Agreement nor any of the rights,
interests or obligations of the Parties under this Agreement shall be assigned
by any Party (whether by operation of law or otherwise) without the prior
written consent of the other Party. Notwithstanding the foregoing, Wintrust and
Merger Co. may assign their respective rights hereunder to another wholly owned
subsidiary of Wintrust. Subject to the foregoing, this Agreement shall be
binding upon and inure to the benefit of the respective successors and assigns
of the Parties.

         10.5 Notices. All notices, requests, demands, and other communications
provided for in this Agreement shall be in writing and shall be deemed to have
been given (a) when delivered in person, (b) the third business day after being
deposited in the United States mail, registered or certified mail (return
receipt requested), or (c) the first business day after being deposited with
Federal Express or any other recognized national overnight courier service, in
each case addressed as follows:

         (i)      If to the Company, addressed to:

                  Advantage National Bank
                  75 East Turner Avenue
                  Elk Grove Village, Illinois 60007
                  Attention:  Gerhardt E. Umlauf, President


                                      A-29



                  with a copy to:

                  Dennis R. Wendte
                  Barack, Ferrazzano, Kirschbaum, Perlman & Nagelberg LLC
                  333 West Wacker Drive, Suite 2700
                  Chicago, Illinois 60606

         (ii)     If to Wintrust or Merger Co., addressed to:

                  Wintrust Financial Corporation
                  727 North Bank Lane
                  Lake Forest, Illinois  60045
                  Attention:       David A. Dykstra
                                   Senior Executive Vice President and
                                   Chief Operating Officer

                  with a copy to:

                  Matthew G. Galo
                  Schiff Hardin & Waite
                  6600 Sears Tower
                  Chicago, IL 60606-6473

         10.6 Counterparts. This Agreement may be executed in any number of
counterparts with the same effect as if the signatures to each counterpart were
upon the same instrument.

         10.7 Knowledge. References in this Agreement to the "knowledge" of a
party shall mean, with respect to a natural person, the actual knowledge of such
person after reasonable investigation and with respect to an entity, the actual
knowledge of its officers and directors after reasonable investigation.

         10.8 Entire Agreement. This Agreement, including the Schedules and
agreements delivered pursuant hereto, and the Confidentiality Agreement sets
forth the entire understanding of the parties and supersedes all prior
agreements, arrangements, and communications, whether oral or written. This
Agreement shall not be modified or amended other than by written agreement of
the parties hereto. Captions appearing in this Agreement are for convenience
only and shall not be deemed to explain, limit, or amplify the provisions
hereof.

         10.9 Governing Law. This Agreement shall be governed by and construed
in accordance with the laws of the State of Illinois, without giving effect to
the conflicts of laws principles thereof.

         10.10 Severability. In the event that a court of competent jurisdiction
shall finally determine that any provision of this Agreement or any portion
thereof is unlawful or unenforceable, such provision or portion thereof shall be
deemed to be severed from this Agreement, and every other provision and portion
thereof that is not invalidated by such determination shall remain in full force
and effect. To the extent that a provision is deemed unenforceable by virtue of
its scope but may be made enforceable by limitation thereof, such provision
shall be enforceable to the fullest extent permitted under the laws and public
policies of the state whose laws are deemed to govern enforceability.


                          ** SIGNATURE PAGE FOLLOWS **


                                      A-30



         IN WITNESS WHEREOF, Wintrust Financial Corporation, Wintrust Merger
Co., and Advantage National Bancorp, Inc. have each executed this Agreement as
of the day and year first written above.

                                  WINTRUST FINANCIAL CORPORATION


                                  By: /s/ Edward J. Wehmer
                                      ------------------------------------------
                                          Edward J. Wehmer
                                          President and Chief Executive Officer


                                  WINTRUST MERGER CO.


                                  By: /s/ David A. Dykstra
                                      ------------------------------------------
                                          David A. Dykstra
                                          Vice President


                                  ADVANTAGE NATIONAL BANCORP, INC.


                                  By: /s/ Gerhardt E. Umlauf
                                      ------------------------------------------
                                          Gerhardt E. Umlauf
                                          President


                                      A-31



                                                                         ANNEX B


                           SECTIONS 11.65 AND 11.70 OF
                                       THE
                        ILLINOIS BUSINESS CORPORATION ACT

5/11.65 RIGHT TO DISSENT -- (a) A shareholder of a corporation is entitled to
dissent from, and obtain payment for his or her shares in the event of any of
the following corporate actions:

                  (1) consummation of a plan of merger or consolidation or a
         plan of share exchange to which the corporation is a party if (i)
         shareholder authorization is required for the merger or consolidation
         of the share exchange by Section 11.20 or the articles of incorporation
         or (ii) the corporation is a subsidiary that is merged with its parent
         or another subsidiary under Section 11.30;

                  (2) consummation of a sale, lease or exchange of all, or
         substantially all, of the property and assets of the corporation other
         than in the usual and regular course of business;

                  (3) an amendment of the articles of incorporation that
         materially and adversely affects rights in respect of a dissenter's
         shares because it:

                           (i) alters or abolishes a preferential right of such
                  shares;

                           (ii) alters or abolishes a right in respect of
                  redemption, including a provision respecting a sinking fund
                  for the redemption or repurchase, of such shares;

                           (iii) in the case of a corporation incorporated prior
                  to January 1, 1982, limits or eliminates cumulative voting
                  rights with respect to such shares; or

                  (4) any other corporate action taken pursuant to a shareholder
         vote if the articles of incorporation, by laws, or a resolution of the
         Board of Directors provide that shareholders are entitled to dissent
         and obtain payment for their shares in accordance with the procedures
         set forth in Section 11.70 or as may be otherwise provided in the
         articles, by-laws or resolution.

         (b) A shareholder entitled to dissent and obtain payment for his or her
shares under this Section may not challenge the corporate action creating his or
her entitlement unless the action is fraudulent with respect to the shareholder
or the corporation or constitutes a breach of a fiduciary duty owed to the
shareholder.

         (c) A record owner of shares may assert dissenters' rights as to fewer
than all the shares recorded in such person's name only if such person dissents
with respect to all shares beneficially owned by any one person and notifies the
corporation in writing of the name and address of each person on whose behalf
the record owner asserts dissenters' rights. The rights of a partial dissenter
are determined as if the shares as to which dissent is made and the other shares
are recorded in the names of different shareholders. A beneficial owner of
shares who is not the record owner may assert dissenters' rights as to shares
held on such person's behalf only if the beneficial owner submits to the
corporation the record owner's written consent to the dissent before or at the
same time the beneficial owner asserts dissenters' rights. (Last amended by P.A.
85-1269, L. `88, eff. 1-1-89.)

5/11.70 PROCEDURE TO DISSENT -- (a) If the corporate action giving rise to the
right to dissent is to be approved at a meeting of shareholders, the notice of
meeting shall inform the shareholders of their right to dissent and the
procedure to dissent. If, prior to the meeting, the corporation furnishes to the
shareholders material information with respect to the transaction that will
objectively enable a shareholder to vote on the transaction and to determine
whether or not to exercise dissenters' rights, a shareholder may assert
dissenters' rights only if the shareholder delivers to the corporation before
the vote is taken a written demand for payment for his or her shares if the
proposed action is consummated, and the shareholder does not vote in favor of
the proposed action.

         (b) If the corporate action giving rise to the right to dissent is not
to be approved at a meeting of shareholders, the notice to shareholders
describing the action taken under Section 11.30 or Section 7.10 shall inform the
shareholders of their right to dissent and the procedure to dissent. If, prior
to or concurrently with the notice, the


                                      B-1



corporation furnishes to the shareholders material information with respect to
the transaction that will objectively enable a shareholder to determine whether
or not to exercise dissenters' rights, a shareholder may assert dissenter's
rights only if he or she delivers to the corporation within 30 days from the
date of mailing the notice a written demand for payment for his or her shares.

         (c) Within 10 days after the date on which the corporate action giving
rise to the right to dissent is effective or 30 days after the shareholder
delivers to the corporation the written demand for payment, whichever is later,
the corporation shall send each shareholder who has delivered a written demand
for payment a statement setting forth the opinion of the corporation as to the
estimated fair value of the shares, the corporation's latest balance sheet as of
the end of a fiscal year ending not earlier than 16 months before the delivery
of the statement, together with the statement of income for that year and the
latest available interim financial statements, and either a commitment to pay
for the shares of the dissenting shareholder at the estimated fair value thereof
upon transmittal to the corporation of the certificate or certificates, or other
evidence of ownership, with respect to the shares, or instructions to the
dissenting shareholder to sell his or her shares within 10 days after delivery
of the corporation's statement to the shareholder. The corporation may instruct
the shareholder to sell only if there is a public market for the shares at which
the shares may be readily sold. If the shareholder does not sell within that 10
day period after being so instructed by the corporation, for purposes of this
Section the shareholder shall be deemed to have sold his or her shares at the
average closing price of the shares, if listed on a national exchange, or the
average of the bid and asked price with respect to the shares quoted by a
principal market maker, if not listed on a national exchange, during that 10 day
period.

         (d) A shareholder who makes written demand for payment under this
Section retains all other rights of a shareholder until those rights are
canceled or modified by the consummation of the proposed corporate action. Upon
consummation of that action, the corporation shall pay to each dissenter who
transmits to the corporation the certificate or other evidence of ownership of
the shares the amount the corporation estimates to be the fair value of the
shares, plus accrued interest, accompanied by a written explanation of how the
interest was calculated.

         (e) If the shareholder does not agree with the opinion of the
corporation as to the estimated fair value of the shares or the amount of
interest due, the shareholder, within 30 days from the delivery of the
corporation's statement of value, shall notify the corporation in writing of the
shareholder's estimated fair value and the amount of interest due and demand
payment for the difference between the shareholder's estimate of fair value and
interest due and the amount of the payment by the corporation or the proceeds of
sale by the shareholder, whichever is applicable because of the procedure for
which the corporation opted pursuant to subsection (c).

         (f) If, within 60 days from delivery to the corporation of the
shareholder notification of estimate of fair value of the shares and interest
due, the corporation and the dissenting shareholder have not agreed in writing
upon the fair value of the shares and interest due, the corporation shall either
pay the difference in value demanded by the shareholder, with interest, or file
a petition in the circuit court of the county in which either the registered
office or the principal office of the corporation is located, requesting the
court to determine the fair value of the shares and interest due. The
corporation shall make all dissenters, whether or not residents of this State,
whose demands remain unsettled parties to the proceeding as an action against
their shares and all parties shall be served with a copy of the petition.
Nonresidents may be served by registered or certified mail or by publication as
provided by law. Failure of the corporation to commence an action pursuant to
this Section shall not limit or affect the right of the dissenting shareholders
to otherwise commence an action as permitted by law.

         (g) The jurisdiction of the court in which the proceeding is commenced
under subsection (f) by a corporation is plenary and exclusive. The court may
appoint one or more persons as appraisers to receive evidence and recommend
decision on the question of fair value. The appraisers have the power described
in the order appointing them, or in any amendment to it.

         (h) Each dissenter made a party to the proceeding is entitled to
judgment for the amount, if any, by which the court finds that the fair value of
his or her shares, plus interest, exceeds the amount paid by the corporation or
the proceeds of sale by the shareholder, whichever amount is applicable.

         (i) The court, in a proceeding commenced under subsection (f), shall
determine all costs of the proceeding, including the reasonable compensation and
expenses of the appraisers, if any, appointed by the court under subsection (g),
but shall exclude the fees and expenses of counsel and experts for the
respective parties. If the fair value of the shares as determined by the court
materially exceeds the amount which the corporation estimated to be the

                                      B-2


fair value of the shares or if no estimate was made in accordance with
subsection (c), then all or any part of the costs may be assessed against the
corporation. If the amount which any dissenter estimated to be the fair value of
the shares materially exceeds the fair value of the shares as determined by the
court, then all or any part of the costs may be assessed against that dissenter.
The court may also assess the fees and expenses of counsel and experts for the
respective parties, in amounts the court finds equitable, as follows:

                  (1) Against the corporation and in favor of any or all
         dissenters if the court finds that the corporation did not
         substantially comply with the requirements of subsections (a), (b),
         (c), (d), or (f).

                  (2) Against either the corporation or as a dissenter and in
         favor of any other party if the court finds that the party against whom
         the fees and expenses are assessed acted arbitrarily, vexatiously, or
         not in good faith with respect to the rights provided by this Section.

                  If the court finds that the services of counsel for any
         dissenter were of substantial benefit to other dissenters similarly
         situated and that the fees for those services should not be assessed
         against the corporation, the court may award to that counsel reasonable
         fees to be paid out of the amounts awarded to the dissenters who are
         benefited. Except as otherwise provided in this Section, the practice,
         procedure, judgment and costs shall be governed by the Code of Civil
         Procedure.

         (j) As used in this Section:

                  (1) "Fair value", with respect to a dissenter's shares, means
         the value of the shares immediately before the consummation of the
         corporate action to which the dissenter objects excluding any
         appreciation or depreciation in anticipation of the corporate action,
         unless exclusion would be inequitable.

                  (2) "Interest" means interest from the effective date of the
         corporate action until the date of payment, at the average rate
         currently paid by the corporation on its principal bank loans or, if
         none, at a rate that is fair and equitable under all the circumstances.
         (Last amended by P.A. 86-1156, L. `90, eff. 8-10-90.)


                                      B-3



                                                                         ANNEX C



                            FORM OF VOTING AGREEMENT

         THIS AGREEMENT ("Agreement") is made and entered into as of the 2nd day
of July, 2003, by and between the undersigned shareholders (each, a
"Shareholder," and collectively, the "Shareholders"), of ADVANTAGE NATIONAL
BANCORP, INC., an Illinois corporation ("ADVANTAGE"), and WINTRUST FINANCIAL
CORPORATION, an Illinois corporation ("WINTRUST").


                                   WITNESSETH:

         WHEREAS, ADVANTAGE, WINTRUST and WINTRUST MERGER CO., an Illinois
corporation ("WMC"), have entered into an Agreement and Plan of Merger dated as
of the date hereof (the "Merger Agreement");

         WHEREAS, it is a condition precedent to Wintrust's obligations under
the Merger Agreement that the Shareholders shall have executed and delivered
this Agreement; and

         WHEREAS, each Shareholder owns and is entitled to vote the number of
issued and outstanding shares of common stock of Advantage (the "Advantage
Common Shares") set forth opposite such Shareholder's name on Schedule 1
attached hereto and has agreed to vote such Shareholder's Advantage Common
Shares pursuant to the terms set forth in this Agreement.

         NOW, THEREFORE, in consideration of the premises and the respective
representations, warranties, covenants and agreements set forth herein, the
Shareholders and Wintrust hereby agree as follows:

           Section 1. Voting of Shares. Each Shareholder hereby agrees that at
any meeting of the shareholders of Advantage and in any action by written
consent of the shareholders of Advantage, such Shareholder shall vote the
Advantage Common Shares which such Shareholder owns and is entitled to vote (a)
in favor of the transactions contemplated by the Merger Agreement, (b) against
any action or agreement which would result in a breach of any term of, or any
other obligation of Advantage under, the Merger Agreement, and (c) against any
action or agreement which would impede, interfere with or attempt to discourage
the transactions contemplated by the Merger Agreement. Each Shareholder agrees
that Advantage shall be authorized to include in any proxy or material
transmitted to shareholders of Advantage, a statement to the effect that the
Shareholder is a party to this Agreement and has committed to vote in favor of
the transactions contemplated by the Merger Agreement.

           Section 2. Term of Agreement. This Agreement shall be effective from
the date hereof and shall terminate and be of no further force and effect upon
the earlier of (i) the Effective Time (as defined in the Merger Agreement), or
(ii) the termination of the Merger Agreement in accordance with its terms.

         Section 3. Covenants of Shareholders. Each Shareholder agrees not to:
except to the extent contained in this Agreement, grant any proxies, deposit any
Advantage Common Shares into a voting trust or enter into a voting agreement
with respect to any Advantage Common Shares; or without the prior written
approval of Wintrust, solicit, initiate or encourage any inquiries or proposals
for a merger or other business combination involving Advantage.

           Section 4. Representations and Warranties of Shareholders. Each
Shareholder represents and warrants to Wintrust as follows: (a) such Shareholder
owns - and is entitled to vote in accordance with such Shareholder's commitments
under this Agreement - the number of Advantage Common Shares set forth opposite
his or her name on Schedule 1 hereto, and, except as disclosed on Schedule
3.3(a) of the Merger Agreement, does not own or have any right to acquire any
Advantage Common Shares not listed on Schedule 1; (b) such Shareholder has the
right, power and authority to execute, deliver and perform under this Agreement;
such execution, delivery and performance will not violate, or require any
consent, approval, or notice under any provision of law or result in the breach
of any outstanding agreements or instruments to which such Shareholder is a
party or is subject; and this Agreement has been duly executed and delivered by
such Shareholder and constitutes a legal, valid and binding agreement of such
Shareholder, enforceable in accordance with its terms; (c) such Shareholder's
Advantage Common Shares listed as owned on Schedule 1 hereto are now and will
remain owned by such Shareholder, free and clear of all voting trusts, voting
agreements, proxies, liens, claims, liabilities, security interests, marital
property rights or any other encumbrances whatsoever (other than (i) pledges for
loans entered into in the ordinary course and (ii) rights of Wintrust and


                                      C-1



encumbrances respecting such Advantage Common Shares created pursuant to this
Agreement or the Merger Agreement); and (d) other than this Agreement and the
Merger Agreement, there are no outstanding options, warrants or rights to
purchase or acquire, or agreements related to, such Shareholder's Advantage
Common Shares.

           Section 5. Representations and Warranties of Wintrust. Wintrust has
the right, power and authority to execute and deliver this Agreement; such
execution and delivery will not violate, or require any consent, approval, or
notice under any provision of law or result in the breach of any outstanding
agreements or instruments to which Wintrust is a party or is subject; and this
Agreement has been duly executed and delivered by Wintrust and constitutes a
legal, valid and binding agreement of Wintrust, enforceable in accordance with
its terms.

           Section 6. Transferability. Neither this Agreement nor any of the
rights, interests or obligations hereunder shall be assigned by any of the
parties hereto (whether by operation of law or otherwise) without the prior
written consent of the other parties, except that Wintrust may assign this
Agreement to a direct or indirect wholly-owned subsidiary or affiliate of
Wintrust, provided that no such assignment shall relieve Wintrust of its
obligations hereunder.

           Section 7. Specific Performance. The parties hereto agree that
irreparable damage would occur in the event that any of the provisions of this
Agreement was not performed by any of the Shareholders in accordance with its
specific terms or was otherwise breached. It is accordingly agreed that Wintrust
shall be entitled to an injunction(s) to prevent breaches of this Agreement by
the Shareholders and to enforce specifically the terms and provisions hereof in
addition to any other remedy to which Wintrust is entitled at law or in equity.

           Section 8. Further Assurances. Each Shareholder agrees to execute and
deliver all such further documents and instruments and take all such further
action as may be necessary or appropriate in order to consummate the
transactions contemplated hereby.

           Section 9. Entire Agreement and Amendment. (a) Except for the Merger
Agreement and its ancillary agreements and instruments, this Agreement contains
the entire agreement between the parties hereto with respect to the transactions
contemplated hereunder and supersedes all prior arrangements or understandings
with respect hereto.

         (b) This Agreement may not be modified, amended, altered or
supplemented except upon the execution and delivery of a written agreement
executed by the parties hereto.

          Section 10. Notices. Each notice, demand or other communication which
may be or is required to be given under this Agreement shall be in writing and
shall be deemed to have been properly given when delivered personally at the
address set forth herein for Wintrust or the address on Schedule 1 for each of
the Shareholders, when sent by facsimile or other electronic transmission to the
respective facsimile transmission numbers of the parties with telephone
confirmation of receipt, or the day after sending by recognized overnight
courier or if by the United States registered or certified mail, return receipt
requested, postage prepaid two days after deposit therein.

          Section 11. General Provisions. This Agreement shall be governed by
the laws of the State of Illinois. This Agreement may be executed in
counterparts, each of which shall be deemed to be an original. Headings are for
convenience only and shall not affect the meaning of this Agreement. Any term of
this Agreement which is invalid or unenforceable shall be ineffective only to
the extent of such invalidity or unenforceability without rendering invalid or
unenforceable the remaining terms of this Agreement.


                            [SIGNATURE PAGE FOLLOWS]


                                      C-2



          IN WITNESS WHEREOF, the parties hereto have executed this Agreement as
 of the day and year first above written.

WINTRUST FINANCIAL CORPORATION, an Illinois Corporation:

By: ______________________________________

Its:______________________________________

Address for Notices:                           With a copy to
  Wintrust Financial Corporation                 Matthew G. Galo
  727 North Bank Lane                            Schiff Hardin & Waite
  Lake Forest, Illinois  60045                   6600 Sears Tower
  Attn: David A. Dykstra                         Chicago, Illinois  60606-6473
        Senior Executive Vice President and
        Chief Operating Officer
  Facsimile No.:  (847) 615-4091                 Facsimile No.:  (312) 258-5700

SHAREHOLDERS:


___________________________________         ___________________________________
Chad Arthur                                 Pat De Moon

___________________________________         ___________________________________
Lee Garr                                    Hank Gianvecchio

___________________________________         ___________________________________
Keith Kotche                                Ed Levato

___________________________________         ___________________________________
Greg Newhuis                                Branka Poplonski

___________________________________         ___________________________________
Pat Ranallo                                 Ed Schwarzer

___________________________________         ___________________________________
Harvey Seybold                              Gayle Smolinski

___________________________________
Gary Umlauf


                                      C-3



                                   SCHEDULE 1


    NAME, ADDRESS AND            NUMBER OF ADVANTAGE        NUMBER OF ADVANTAGE
   FACSIMILE NUMBER OF         COMMON SHARES OWNED BY     COMMON SHARES ISSUABLE
     SHAREHOLDER                     SHAREHOLDER          UNDER OPTIONS/WARRANTS
                                                            HELD BY SHAREHOLDER

Chad Arthur                              170                           0

Lee Garr                              13,667                      16,334

Keith Kotche                          31,807                      29,667

Greg Newhuis                          16,999                      18,166

Pat Ranallo                           38,666                       1,500

Harvey Seybold                         7,000                       8,167

Gary Umlauf                           22,866                      37,387

Pat De Moon                            8,798                      19,667

Hank Gianvecchio                       9,001                      17,167

Ed Levato                             50,334                      53,000

Branka Poplonski                      16,573                      19,240

Ed Schwarzer                          48,667                      13,000

Gayle Smolinski                          333                       1,500

Mark Stetson                           4,145                      10,000

Paul Katauskas                             0                       7,225


                                      C-4





                                     PART II

                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 20.  INDEMNIFICATION OF OFFICERS AND DIRECTORS.

         In accordance with the Illinois Business Corporation Act (being Chapter
805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of the
Registrant's Certificate of Incorporation provide as follows:

         ARTICLE EIGHT: No director of the corporation shall be liable to the
corporation or its shareholders for monetary damages for breach of fiduciary
duty as a director except for liability (a) for any breach of the director's
duty of loyalty to the corporation or its shareholders, (b) for acts or
omissions not in good faith or that involve intentional misconduct or a knowing
violation of law, (c) under Section 8.65 of the BCA, as the same exists or
hereafter may be amended, or (d) for any transaction from which the director
derived an improper personal benefit.

         ARTICLE NINE, PARAGRAPH 1: The corporation shall indemnify, to the full
extent that it shall have power under applicable law to do so and in a manner
permitted by such law, any person made or threatened to be made a party to any
threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative, by reason of the fact that he or she
is or was a director, officer, employee or agent of the corporation, or who is
or was serving at the request of the corporation as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust or
other enterprise against liabilities and expenses reasonably incurred or paid by
such person in connection with such action, suit or proceeding. The corporation
may indemnify, to the full extent that it shall have power under applicable law
to do so and in a manner permitted by such law, any person made or threatened to
be made a party to any threatened, pending or completed action, suit or
proceeding, whether civil, criminal, administrative or investigative, by reason
of the fact that he or she is or was a director, officer, employee or agent of
the corporation, or is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise against liabilities and expenses reasonably
incurred or paid by such person in connection with such action, suit or
proceeding. The words "liabilities" and "expenses" shall include, without
limitation: liabilities, losses, damages, judgments, fines, penalties, amounts
paid in settlement, expenses, attorneys' fees and costs. Expenses incurred in
defending a civil, criminal, administrative, investigative or other action, suit
or proceeding may be paid by the corporation in advance of the final disposition
of such action, suit or proceeding in accordance with the provisions of Section
8.75 of the BCA.

         The indemnification and advancement of expenses provided by this
Article shall not be deemed exclusive of any other rights to which any person
indemnified may be entitled under any statute, by-law, agreement, vote of
shareholders, or disinterested directors or otherwise, both as to action in his
official capacity and as to action in any other capacity while holding such
office, and shall continue as to a person who has ceased to be such director,
officer, employee or agent and shall inure to the benefit of the heirs,
executors and administrators of such person.

         PARAGRAPH 2: The corporation may purchase and maintain insurance on
behalf of any person referred to in the preceding paragraph against any
liability asserted against him or her and incurred by him or her in any such
capacity, or arising out of his or her status as such, whether or not the
corporation would have the power to indemnify him or her against such liability
under the provisions of this Article or otherwise.

         PARAGRAPH 3: For purposes of this Article, references to "the
corporation" shall include, in addition to the resulting corporation, any
constituent corporation (including any constituent of a constituent) absorbed in
a consolidation or merger which, if its separate existence had continued, would
have had power and authority to indemnify its directors, officers, employees or
agents, so that any person who is or was a director, officer, employee or agent
of such constituent corporation, or is or was serving at the request of such
constituent corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise, shall stand
in the same position under the provisions of this Article with respect to the
resulting or surviving corporation as he or she would have with respect to such
constituent corporation if its separate existence had continued.

         PARAGRAPH 4: The provisions of this Article shall be deemed to be a
contract between the corporation and each director or officer who serves in any
such capacity at any time while this Article and the relevant provisions of the
BCA, or other applicable law, if any, are in effect, and any repeal or
modification of any such law or of this


                                      II-1



Article shall not affect any rights or obligations then existing with respect to
any state of facts then or theretofore existing or any action, suit or
proceeding theretofore or thereafter brought or threatened based in whole or in
part upon any such state of facts.

         PARAGRAPH 5: For purposes of this Article, references to "other
enterprises" shall include employee benefit plans; references to "fines" shall
include any excise taxes assessed on a person with respect to any employee
benefit plan; and references to "serving at the request of the corporation"
shall include any service as a director, officer, employee or agent of the
corporation which imposes duties on, or involves services by, such director,
officer, employee or agent with respect to any employee benefit plan, its
participants, or beneficiaries; and a person who acted in good faith and in a
manner he or she reasonably believed to be in the interest of the participants
and beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner not opposed to the best interests of the corporation.

         Section 6.3 of the Registrant's By-laws provides as follows:

         SECTION 6.3. MANDATORY INDEMNIFICATION. To the extent that a director,
officer, employee or agent of a corporation, or any subsidiary or subsidiaries,
as the case may be, has been successful on the merits or otherwise in defense of
any action, suit or proceeding referred to in Sections 6.1 and 6.2, or in
defense of any claim, issue or matter therein, such person shall be indemnified
against expenses (including attorneys' fees) actually and reasonably incurred by
him or her in connection therewith.

         The Illinois Business Corporation Act provides for indemnification of
officers, directors, employees and agents as follows:

         5/8.75 INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS;
INSURANCE. (a) A corporation may indemnify any person who was or is a party, or
is threatened to be made a party to any threatened, pending or completed action,
suit or proceeding, whether civil, criminal, administrative or investigative
(other than an action by or in the right of the corporation) by reason of the
fact that he or she is or was a director, officer, employee or agent of the
corporation, or who is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise, against expenses (including attorneys'
fees), judgments, fines and amounts paid in settlement actually and reasonably
incurred by such person in connection with such action, suit or proceeding, if
such person acted in good faith and in a manner he or she reasonably believed to
be in, or not opposed to the best interests of the corporation, and, with
respect to any criminal action or proceeding, had no reasonable cause to believe
his or her conduct was unlawful. The termination of any action, suit or
proceeding by judgment, order, settlement, conviction, or upon a plea of nolo
contendere or its equivalent, shall not, of itself, create a presumption that
the person did not act in good faith and in a manner which he or she reasonably
believed to be in or not opposed to the best interests of the corporation or,
with respect to any criminal action or proceeding, that the person had
reasonable cause to believe that his or her conduct was unlawful.

         (b) A corporation may indemnify any person who was or is a party,
or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in
its favor by reason of the fact that such person is or was a director, officer,
employee or agent of the corporation, or is or was serving at the request of the
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees) actually and reasonably incurred by such person in
connection with the defense or settlement of such action or suit, if such person
acted in good faith and in a manner he or she reasonably believed to be in, or
not opposed to, the best interests of the corporation, provided that no
indemnification shall be made with respect to any claim, issue, or matter as to
which such person has been adjudged to have been liable to the corporation,
unless, and only to the extent that the court in which such action or suit was
brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, such person is
fairly and reasonably entitled to indemnity for such expenses as the court shall
deem proper.

         (c) To the extent that a present or former director, officer or
employee of a corporation has been successful, on the merits or otherwise, in
the defense of any action, suit or proceeding referred to in subsections (a) and
(b), or in defense of any claim, issue or matter therein, such person shall be
indemnified against expenses (including attorneys' fees) actually and reasonably
incurred by such person in connection therewith if the person


                                      II-2



acted in good faith and in a manner he or she reasonably believed to be in, or
not opposed to, the best interests of the corporation.

         (d) Any indemnification under subsections (a) and (b) (unless ordered
by a court) shall be made by the corporation only as authorized in the specific
case, upon a determination that indemnification of the present or former
director, officer, employee or agent is proper in the circumstances because he
or she has met the applicable standard of conduct set forth in subsections (a)
or (b). Such determination shall be made with respect to a person who is a
director or officer at the time of the determination: (1) by the majority vote
of the directors who are not parties to such action, suit or proceeding, even
though less than a quorum, (2) by a committee of the directors designated by a
majority vote of the directors, even though less than a quorum, (3) if there are
no such directors, or if the directors so direct, by independent legal counsel
in a written opinion, or (4) by the shareholders.

         (e) Expenses (including attorney's fees) incurred by an officer or
director in defending a civil or criminal action, suit or proceeding may be paid
by the corporation in advance of the final disposition of such action, suit or
proceeding upon receipt of an undertaking by or on behalf of the director or
officer to repay such amount if it shall ultimately be determined that such
person is not entitled to be indemnified by the corporation as authorized in
this Section. Such expenses (including attorneys' fees) incurred by former
directors and officers or other employees and agents may be so paid on such
terms and conditions, if any, as the corporation deems appropriate.

         (f) The indemnification and advancement of expenses provided by or
granted under the other subsections of this Section shall not be deemed
exclusive of any other rights to which those seeking indemnification or
advancement of expenses may be entitled under any by-law, agreement, vote of
shareholders or disinterested directors, or otherwise, both as to action in his
or her official capacity and as to action in another capacity while holding such
office.

         (g) A corporation may purchase and maintain insurance on behalf of any
person who is or was a director, officer, employee or agent of the corporation,
or who is or was serving at the request of the corporation as a director,
officer, employee or agent of another corporation, partnership, joint venture,
trust or other enterprise, against any liability asserted against such person
and incurred by such person in any such capacity, or arising out of his or her
status as such, whether or not the corporation would have the power to indemnify
such person against such liability under the provisions of this Section.

         (h) If a corporation indemnifies or advances expenses to a director or
officer under subsection (b) of this Section, the corporation shall report the
indemnification or advance in writing to the shareholders with or before the
notice of the next shareholders meeting.

         (i) For purposes of this Section, references to "the corporation" shall
include, in addition to the surviving corporation, any merging corporation
(including any corporation having merged with a merging corporation) absorbed in
a merger which, if its separate existence had continued, would have had the
power and authority to indemnify its directors, officers, and employees or
agents, so that any person who was a director, officer, employee or agent of
such merging corporation, or was serving at the request of such merging
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, shall stand in the same
position under the provisions of this Section with respect to the surviving
corporation as such person would have with respect to such merging corporation
if its separate existence had continued.

         (j) For purposes of this Section, reference to "other enterprises"
shall include employee benefit plans; references to "fines" shall include any
excise taxes assessed on a person with respect to an employee benefit plan; and
references to "serving at the request of the corporation" shall include any
service as a director, officer, employee or agent of the corporation which
imposes duties on, or involves services by such director, officer, employee, or
agent with respect to an employee benefit plan, its participants, or
beneficiaries. A person who acted in good faith and in a manner he or she
reasonably believed to be in the best interests of the participants and
beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner "not opposed to the best interest of the corporation" as referred to in
this Section.

         (k) The indemnification and advancement of expenses provided by or
granted under this Section shall, unless otherwise provided when authorized or
ratified, continue as to a person who has ceased to be a director, officer,
employee, or agent and shall inure to the benefit of the heirs, executors, and
administrators of that person.


                                      II-3



         (l) The changes to this Section made by this amendatory Act of the 92nd
General Assembly apply only to actions commenced on or after the effective date
of this amendatory Act of the 92nd General Assembly. (Last amended by P.A.
92-0033, L. '01, eff. 7-1-01.)

         Wintrust has purchased $30 million of insurance policies which insure
Wintrust's directors and officers against liability which they may incur as a
result of actions taken in such capacities. In addition, Wintrust maintains
fiduciary liability coverage up to a $5 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 21.  EXHIBITS AND FINANCIAL STATEMENT SCHEDULES.

         (a) Exhibits:

         A list of the exhibits included as part of this registration statement
is set forth on the list of exhibits immediately preceding such exhibits and is
incorporated herein by reference.

         (b) Financial Statement Schedules:

         All schedules for which provision is made in the applicable accounting
regulations of the Securities and Exchange Commission have been omitted because
they are not required, amounts which would otherwise be required to be shown
with respect to any item are not material, are inapplicable or the required
information has already been provided elsewhere or incorporated by reference in
the registration statement.

ITEM 22:  UNDERTAKINGS.

         (a) The undersigned registrant hereby undertakes to respond to requests
for information  that is incorporated by reference into the prospectus  pursuant
to Item 4, 10(b), 11, or 13 of this form,  within one business day of receipt of
such  request,  and to send the  incorporated  documents  by first class mail or
other equally  prompt means.  This includes  information  contained in documents
filed subsequent to the effective date of the registration statement through the
date of responding to the request.

         (b) The undersigned  registrant hereby undertakes to supply by means of
a post-effective  amendment all information  concerning a transaction,  and the
company  being  acquired  involved  therein,  that  was not the  subject  of and
included in the registration statement when it became effective.

         (c) The undersigned  registrant hereby undertakes that, for purposes of
determining  any liability  under the Securities Act of 1933, each filing of the
registrant's  annual  report  pursuant to Section  13(a) or Section 15(d) of the
Securities  Exchange Act of 1934, as amended,  that is incorporated by reference
in  this  Registration  Statement  shall  be  deemed  to be a  new  registration
statement  relating to the securities  offered herein,  and the offering of such
securities  at that time shall be deemed to be the  initial  bona fide  offering
thereof.

         (d)  Insofar  as  indemnification  for  liabilities  arising  under the
Securities Act of 1933 may be permitted to directors,  officers and  controlling
persons of the registrant  pursuant to the foregoing  provisions,  or otherwise,
the  registrant  has been  advised  that in the  opinion of the  Securities  and
Exchange  Commission such  indemnification is against public policy as expressed
in the Act and is,  therefore,  unenforceable.  In the  event  that a claim  for
indemnification  against  such  liabilities  (other  than  the  payment  by  the
registrant of expenses  incurred or paid by a director,  officer or  controlling
person of the  registrant  in the  successful  defense  of any  action,  suit or
proceeding)  is  asserted by such  director,  officer or  controlling  person in
connection with the securities being registered,  the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit  to a  court  of  appropriate  jurisdiction  the  question  whether  such
indemnification  by it is  against  policy as  expressed  in the Act and will be
governed by the final adjudication of such issue.

         (e)      The undersigned registrant hereby undertakes that:

                  (1) For purposes of determining any liability under the
         Securities Act of 1933, the information omitted from the form of
         prospectus filed as part of this registration statement in reliance
         upon Rule 430A and contained in a form of prospectus filed by the
         registrant pursuant to Rule 424(b)(1) or (4) or


                                      II-4



         497(h) under the Securities Act shall be deemed to be part of this
         registration statement as of the time it was declared effective.

                  (2) For the purpose of determining any liability under the
         Securities Act of 1933, each post-effective amendment that contains a
         form of prospectus shall be deemed to be a new registration statement
         relating to the securities offered therein, and the offering of such
         securities at that time shall be deemed to be the initial bona fide
         offering thereof.

                                      II-5



                                   SIGNATURES


         Pursuant to the requirements of the Securities Act of 1933, as amended,
the registrant has duly caused this Amendment No. 1 to the Registration
Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the City of Lake Forest, State of Illinois, on this 2nd day of
September, 2003.


                                  WINTRUST FINANCIAL CORPORATION

                                  By:/s/ David A. Dykstra
                                     -------------------------------------------
                                     David A. Dykstra
                                     Senior Executive Vice President and Chief
                                     Operating Officer






         Pursuant to the requirements of the Securities Act of 1933, as amended,
this Registration Statement has been signed by the following persons in the
capacities and on the date indicated.



                 NAME                                          TITLE                                  DATE
                 ----                                          -----                                  ----
                                                                                           


/s/ Edward J. Wehmer                                  President, Chief Executive                 September 2, 2003
---------------------------------------                 Officer and Director
Edward J. Wehmer

/s/ David L. Stoehr                                  Executive Vice President and                September 2, 2003
---------------------------------------               Chief Financial Officer
David L. Stoehr                                    (Principal Accounting Officer)


/s/John S. Lillard*                                     Chairman and Director                    September 2, 2003
---------------------------------------
John S. Lillard

/s/ Peter D. Crist*                                            Director                          September 2, 2003
---------------------------------------
Peter D. Crist

/s/ Bruce K. Crowther*                                         Director                          September 2, 2003
---------------------------------------
Bruce K. Crowther

/s/ Bert A. Getz, Jr.*                                         Director                          September 2, 2003
---------------------------------------
Bert A. Getz, Jr.

/s/ Philip W. Hummer*                                          Director                          September 2, 2003
---------------------------------------
Philip W. Hummer

/s/ James B. McCarthy*                                         Director                          September 2, 2003
---------------------------------------
James B. McCarthy

/s/ Marguerite Savard McKenna*                                Director                           September 2, 2003
---------------------------------------
Marguerite Savard McKenna

/s/ Albin F. Moschner*                                        Director                           September 2, 2003
---------------------------------------
Albin F. Moschner

/s/ Thomas J. Neis*                                           Director                           September 2, 2003
---------------------------------------
Thomas J. Neis


                                       S-1



                 NAME                                          TITLE                                  DATE
                 ----                                          -----                                  ----


/s/ Hollis W. Rademacher*                                     Director                           September 2, 2003
---------------------------------------
Hollis W. Rademacher

J. Christopher Reyes*                                         Director                           September 2, 2003
---------------------------------------
J. Christopher Reyes

/s/ John J. Schornack*                                        Director                           September 2, 2003
---------------------------------------
John J. Schornack

Ingrid S. Stafford*                                           Director                           September 2, 2003
---------------------------------------
Ingrid S. Stafford


------------------
* Signed pursuant to power of attorney.

By:  /s/ David A. Dykstra
     ----------------------------------
     David A. Dykstra
     Attorney-in-fact


                                       S-2



                                INDEX TO EXHIBITS

EXHIBIT
NUMBER   DESCRIPTION OF EXHIBIT
----     ----------------------


2.1      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, Wintrust Merger Co. and Advantage National Bancorp, Inc.
         dated July 2, 2003 (Included as Annex A to this proxy
         statement/prospectus).

2.2      Agreement and Plan of Merger by and among Wintrust Financial
         Corporation, WTFC Merger Co., and Village Bancorp, Inc. dated August 7,
         2003.+

3.1      Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

3.2      Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

3.3      Amended and Restated By-laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q
         for the quarter ended March 31, 2003).

4.1      Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C.*

8.1      Tax Opinion of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLC.+

23.1     Consent of Ernst & Young LLP.+

24.1     Power of Attorney (contained in signature page to the registration
         statement).

99.1     Form of Proxy for Special Meeting of Advantage*


---------------------------
+       Filed herewith.


*       Previously filed.