Edgar Filing: WINTRUST FINANCIAL CORP

PROSPECTUS Filed pursuant to Rule 424(b)(4)
---------- File No. 333-89606

1,185,000 SHARES
WINTRUST FINANCIAL CORPORATION
COMMON STOCK
-----------------------

Wintrust Financial Corporation is offering 1,185,000 shares of its common stock.

Our common stock is traded on the Nasdaq National Market under the symbol
"WTFC." The last reported sale price of our common stock as reported on Nasdaq
on June 10, 2002 was $28.85 per share.

INVESTING IN OUR COMMON STOCK INVOLVES RISKS THAT ARE DESCRIBED IN THE "RISK
FACTORS" SECTION BEGINNING ON PAGE 12.

----------------------
PRICE $28.70 PER SHARE
----------------------

PER SHARE TOTAL
----------- ------------

Public offering price...................... $28.70 $34,009,500
Underwriting discount...................... $ 1.72 $ 2,038,200
Proceeds, before expenses, to Wintrust.... $26.98 $31,971,300

The underwriters may also purchase up to an additional 177,750 shares of common
stock from us at the public offering price, less the underwriting discount,
within 30 days from the date of this prospectus to cover over-allotments, if
any.

NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
COMMISSION HAS APPROVED OR DISAPPROVED OF THESE SECURITIES OR DETERMINED IF THIS
PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.

The shares of common stock will be ready for delivery on or about June 14, 2002.

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

RBC CAPITAL MARKETS

U.S. BANCORP PIPER JAFFRAY

STIFEL, NICOLAUS & COMPANY
INCORPORATED

RAYMOND JAMES

-------------
June 11, 2002

[MAP SHOWING COMPANY'S FACILITIES]

TABLE OF CONTENTS

PAGE
----

Prospectus Summary............................................................1
Summary Consolidated Financial Data...........................................9
Risk Factors.................................................................12
Use of Proceeds..............................................................18
Capitalization...............................................................18
Price Range of Common Stock and Dividend Policy..............................19
Underwriting.................................................................20
Transfer Agent...............................................................21
Legal Matters................................................................22
Experts ....................................................................22
Where You Can Find More Information..........................................22
Documents Incorporated By Reference..........................................22

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

You should rely only on the information provided or incorporated by
reference in this prospectus. We have not, and the underwriters have not,
authorized any other person to provide you with different information. This
prospectus is not an offer to sell, nor is it seeking an offer to buy, our
common stock in any state where the offer or sale is not permitted. The
information in this prospectus is complete and accurate only as of the date of
this prospectus.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

We make certain forward-looking statements in this prospectus that are
based upon our current expectations and projections about current events. We
intend these forward-looking statements to be covered by the safe harbor
provisions for forward-looking statements contained in the Private Securities
Litigation Reform Act of 1995, and we are including this statement for purposes
of these safe harbor provisions. 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 our goals, intentions and expectations;

o our business plans and growth strategies; and

o estimates of our 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
"Risk Factors" beginning on page 12.

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

PROSPECTUS SUMMARY

The items in the following summary are described in more detail later
in this prospectus or in the other information incorporated by reference into
this prospectus. This summary provides an overview of selected information and
does not contain all of the information you should consider. Therefore, you
should also read the more detailed information included in this prospectus, our
consolidated financial statements and the other information that is incorporated
by reference in this prospectus before making a decision to invest in our common
stock. Unless otherwise indicated, the information in this prospectus assumes
that the underwriters will not exercise their option to purchase additional
shares to cover over-allotments.

WINTRUST FINANCIAL CORPORATION

We are a financial holding company headquartered in Lake Forest,
Illinois, with total assets of approximately $3.0 billion at March 31, 2002. We
operate seven community banks, all in affluent suburbs of Chicago, which provide
community-oriented, personal and commercial banking services primarily to
individuals and small to mid-size businesses through 31 banking facilities. Each
of our banks provides a full complement of commercial and consumer loan and
deposit products and services. Since late 1998, we have provided trust and
investment services through our asset management subsidiary to customers of our
banks. Through Wayne Hummer Investments LLC and Wayne Hummer Management Company,
firms we acquired in February 2002 to expand our asset management business, we
now provide brokerage and trust and investment services to over 35,000
customers, primarily in the Midwest, as well as to customers of our banks. In
addition, we are involved in specialty lending through operating subsidiaries or
divisions of certain of our banks. Our 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.

FINANCIAL SUMMARY

The following table highlights the financial growth and performance of
our organization for the five-year period ended December 31, 2001 and
three-month periods ended March 31, 2002 and March 31, 2001.

AS OF OR FOR THE
THREE MONTHS ENDED
MARCH 31, AS OF OR FOR THE YEAR ENDED DECEMBER 31,
------------------- ------------------------------------------------------------
2002 2001 2001 2000 1999 1998 1997
------ ------ ------ ------ ------ ------ ------
(DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)

Total revenue............... $ 34,920 $ 24,126 $ 102,812 $ 79,306 $ 57,542 $ 44,839 $ 31,716
Net income.................. 6,362 3,904 18,439 11,155 9,427 6,245 4,846
Earnings per share
(diluted)................ 0.40 0.29 1.27 0.83 0.73 0.49 0.40
Total assets................ 2,955,153 2,166,630 2,705,422 2,102,806 1,679,382 1,348,048 1,053,400
Loans....................... 2,167,550 1,625,979 2,018,479 1,547,596 1,270,126 974,031 702,700
Deposits.................... 2,417,315 1,916,756 2,314,636 1,826,576 1,463,622 1,229,154 917,701
Common shareholders'
equity................... 163,521 105,872 141,278 102,276 92,947 75,205 68,790
Return on average assets.... 0.92% 0.75% 0.79% 0.60% 0.63% 0.53% 0.56%
Return on average equity.... 17.12% 15.39% 15.24% 11.51% 11.58% 8.68% 7.88%

The following table shows the compound annual growth rates we achieved
over the one-, two-, three- and four-year periods ended December 31, 2001. Based
on our business strategy and growth plans, we expect to continue to post higher
than average growth rates in future periods.

COMPOUND ANNUAL GROWTH RATES
----------------------------------------
1 YEAR(1) 2 YEAR 3 YEAR 4 YEAR
---------- -------- --------- ---------
Total revenue..................... 29.6% 33.7% 31.9% 34.2%
Net income........................ 34.0 39.9 43.5 39.7
Earnings per share (diluted)...... 23.3 31.9 37.4 33.5
Total assets...................... 28.7 26.9 26.1 26.6
Loans............................. 30.4 26.1 27.5 30.2
Deposits.......................... 26.7 25.8 23.5 26.0
Common shareholders' equity....... 38.1 23.3 23.4 19.7

-----------------
(1) Net income and earnings per share exclude a non-recurring
after-tax charge of $2.6 million reported in 2000.

The following table provides information regarding each of our banks.

TOTAL ASSETS AT CURRENT
MARCH 31, 2002 NUMBER OF
BANK DATE OPENED (IN THOUSANDS) FACILITIES
---- ----------- -------------- ----------

Lake Forest........................... December 1991 $722,531 7
Hinsdale.............................. October 1993 533,083 5
North Shore Community................. September 1994 581,032 7
Libertyville.......................... October 1995 382,244 5
Barrington............................ December 1996 329,244 2
Crystal Lake.......................... December 1997 194,130 4
Northbrook............................ November 2000 116,972 1

COMMUNITY BANKING

Each of our banking subsidiaries was founded as a de novo, or new,
banking organization within the last approximately ten years. We have grown from
$1.1 billion in assets at December 31, 1997 to approximately $3.0 billion in
assets at March 31, 2002, and our diluted earnings per share have increased at a
compound annual growth rate of 33.5% over the four-year period ended December
31, 2001. Our historical financial performance has been affected by costs
associated with growing market share in deposits and loans, opening new banks
and branch facilities and building an experienced management team. Our recent
financial performance generally reflects the improved profitability of our
operating subsidiaries as they mature, offset by the costs of opening new banks
and branch facilities. Our experience has been that it generally takes from 13
to 24 months for new banks to first achieve operational profitability depending
on the number and timing of branch facilities added.

ASSET MANAGEMENT AND BROKERAGE SERVICES

Since late 1998, we have offered trust services in the communities
served by our banks through Wintrust Asset Management Company. We employ
experienced trust personnel and offer a full range of trust and investment
services at Lake Forest Bank, North Shore Community Bank, Hinsdale Bank,
Barrington Bank and Northbrook Bank. Prospective trust and investment customers
at our other two banks are currently being served on an appointment basis.

To expand our asset management business and to enter into the
securities brokerage business, on February 20, 2002, we completed our
acquisition of Wayne Hummer Investments, LLC, a registered broker-dealer, Wayne
Hummer Management Company, a registered investment adviser, and Focused
Investments LLC, a broker-dealer and wholly-owned subsidiary of Wayne Hummer
Investments, each based in Chicago. We collectively refer to the businesses we
acquired as the Wayne Hummer Companies. The acquisition has enabled us to
augment fee-based revenue and to diversify our revenue stream by adding
brokerage services as well as offering traditional banking products to the
customers of the Wayne Hummer Companies. We paid $28 million for the Wayne
Hummer Companies, consisting of $8 million in cash, 762,742 shares of common
stock (then valued at $15 million) and $5 million of deferred cash payments to
be made over a three-year period subsequent to the closing date. We also agreed
to pay additional consideration contingent upon the attainment of certain
performance measures over the next five years. We intend to continue to use the
Wayne Hummer name in our brokerage and asset management operations. Effective
May 20, 2002, the name of Wintrust Asset Management Company was changed to Wayne
Hummer Trust Company.

Through Wayne Hummer Investments, which we are currently operating as a
separate subsidiary of Wintrust, we provide a full range of private client and
securities brokerage services to approximately 35,000 customers, located
primarily in the Midwest, with client assets of approximately $4.0 billion at
March 31, 2002. Focused Investments provides a full range of investment services
to clients through a network of relationships with community-based financial
institutions primarily in Illinois. Wayne Hummer Management Company provides
money management services and advisory services to individuals and institutions,
municipal and tax-exempt organizations, and four proprietary mutual funds. Wayne
Hummer Management Company also provides portfolio management and financial
supervision for a wide range of pension and profit-sharing plans. Individual
accounts managed by Wayne Hummer Management Company totaled approximately $427
million at March 31, 2002, while the four managed funds had approximately $625
million in total assets at March 31, 2002. Wayne Hummer Management will continue
to manage its mutual funds. Subject to bank regulatory approval, we plan to
combine the individual account management part of this business with Wayne
Hummer Trust Company, which at March 31, 2002, managed approximately $447
million of assets.

SPECIALTY LENDING

We conduct our specialty lending businesses through direct and indirect
non-bank subsidiaries and divisions of our banks.

Through First Insurance Funding we make loans to businesses to finance
the insurance premiums they pay on their commercial insurance policies. The
loans are originated by First Insurance Funding working through independent
medium and large insurance agents and brokers located throughout the nation. The
insurance premiums we finance are primarily for commercial customers' purchases
of liability, property and casualty and other commercial insurance. This lending
involves relatively rapid turnover of the loan portfolio and high volume of loan
originations. Because of the indirect nature of this lending and because the
borrowers are located nationwide, this segment may be more susceptible to third
party fraud. The majority of these loans are purchased by our banks in order to
more fully utilize their lending capacity. These loans generally provide the
banks higher yields than alternative investments. Since the second quarter of
1999, we have also been selling some of the loan originations to an unrelated
third party with servicing retained. Based on limited industry data available in
certain state regulatory filings and First Insurance Funding management's
experience in and knowledge of the premium finance industry, management
estimates that, ranked by origination volumes, First Insurance Funding is one of
the top five premium finance companies operating in the United States, with loan
origination volume of approximately $1.3 billion during 2001. Our premium
finance loans as of March 31, 2002, were $414.3 million, or 19% of our loan
portfolio.

Through Tricom, Inc. we provide high-yielding, short-term accounts
receivable financing and value-added, outsourced administrative services, such
as data processing of payrolls, billing and cash management services to the
temporary staffing industry. Tricom's clients, located throughout the United
States, provide staffing services to businesses in diversified industries.
During 2001, Tricom processed payrolls with associated client billings of
approximately $248 million and contributed $7.5 million of revenues, net of
interest expense, to us.

We engage in other specialty lending through divisions of our banks,
including indirect auto lending which we conduct through a division of Hinsdale
Bank. The indirect automobile loans are diversified among many individual
borrowers, secured by new and used automobiles and are generated by a large
network of automobile dealers located in the Chicago area with which we have
established relationships. Like other consumer loans, the indirect auto loans
are subject to the banks' established credit standards. We regard substantially
all of these loans as prime quality loans. Management continually monitors the
dealer relationships to deter third party fraud, and the banks are not dependent
on any one dealer as a source of such loans. At March 31, 2002, our indirect
auto loans were $184.4 million and comprised approximately 9% of our loan
portfolio. Management is not pursuing growth in this segment and anticipates
that this portfolio will comprise a smaller portion of the net loan portfolio in
the future.

OPERATIONAL STRATEGY

Since our first bank was opened in 1991, we have been committed to the
same fundamental operational strategy, the key elements of which include the
following:

o MAINTAINING DECISION-MAKING AUTHORITY LOCALLY WITHIN EACH OF
OUR BANKS AND PROVIDING A HIGH LEVEL OF PERSONAL AND
PROFESSIONAL SERVICE. Our community banking philosophy is
driven by our emphasis on local independence and
decision-making authority within each of our banks. While
senior management of Wintrust provides expertise to each of
our subsidiaries in the areas of capital planning, long-term
strategic planning, marketing and advertising, financial
management, investment and asset/liability management, and
technology, the separate management teams of each of the
banks, as well as First Insurance, Wayne Hummer Trust Company,
Tricom and the Wayne Hummer Companies, have full managerial
responsibilities for customer service and the ongoing
day-to-day operations of their respective organizations,
subject to the oversight of our Board of Directors and the
boards of our subsidiaries. Our banks enjoy the competitive
advantages of being able to tailor products and services to
meet the differing needs of the customers that they serve, to
quickly make decisions affecting customers, and to participate
actively in their communities.

o EMPLOYING FEWER, BUT HIGHLY QUALIFIED AND PRODUCTIVE
INDIVIDUALS AT RELATIVELY HIGH COMPENSATION RATES AND FOCUSING
ON LOW NET OVERHEAD RATIOS. Key to our growth and
profitability is our management's extensive experience in
providing community banking services, and retaining highly
qualified managers is critical to our strategy. Our banks'
presidents and chief executive officers were selected not only
for their years of banking experience but also for their
business development skills and their strong ties to the
communities they serve. Our practice of employing fewer, but
highly qualified individuals at all levels of the organization
is key to maintaining a decentralized management structure.
Although our management compensation levels may be relatively
high, we believe our organizational structure allows us to
continue to improve and maintain favorable net overhead ratios
as the banks, First Insurance, Wayne Hummer Trust Company and
Tricom mature.

o MARKETING INNOVATIVE DEPOSIT AND LOAN PRODUCTS. Our banks
offer local residents competitive retail products designed to
attract customers and to provide the banks with the
opportunity to introduce and cross-sell their full range of
personalized banking services. Each of our banks has developed
a strong customer base within its communities through the
utilization of innovative community-oriented marketing
programs. Our banks market their products aggressively through
creative newspaper and other advertising, special promotions
and frequently sponsored community events. While competitive
pricing may create pressure on our net interest margin at
times, to be more responsive to the needs of consumers in
their specific markets, the banks have also introduced a
variety of innovative deposit and loan products to appeal to
the unique needs of different types of bank customers, such as
different age groups and other special segments of the target
markets. In addition, each of our banks has a large board of
directors comprised of influential business persons and
prominent individuals within their respective communities who
assist the banking officers with business development.
Consequently, we believe substantially all of our deposits are
relatively stable, core deposits. We have been successful in
growing our deposits at a compound annual growth rate of 26.0%
from December 31, 1997 through December 31, 2001.

o PURSUING A NUMBER OF SPECIALTY LENDING NICHES. We currently
finance loans in several different specialty lending niches to
more fully utilize our lending capacity, to diversify our loan
portfolio, and to enhance the profitability of our banks. In
addition to premium finance loans originated by First
Insurance, short-term accounts receivables financed by Tricom,
and indirect auto loans, we also engage in mortgage warehouse
lending, medical and municipal equipment leasing, homeowners
and condominium association lending and, more recently, small
aircraft lending. Loans in our specialty lending niches tend
to be higher yielding than other commercial and consumer loans
in our banks' portfolios, but may involve greater credit risks
than generally associated with loan portfolios of more
traditional community banks due to marketability of the
collateral or because we do not have direct customer
relationships with the underlying borrowers.

o FOCUS ON GENERATING FEE INCOME TO AUGMENT NET INTEREST INCOME.
During 2001, we generated fee income from a variety of sources
including the origination and sale of mortgage loans, account
service charges, trust and asset management fees, premium
income from call option contracts, as well as gains on sales
of premium finance receivables and securities. In addition, we
earn administrative fees at Tricom related to its payroll
processing business. We have further diversified our sources
of fee income with the acquisition of the Wayne Hummer
Companies which will increase our noninterest income as a
percentage of net revenues in 2002. Non-interest income (not
including the $1.25 million we recovered during the quarter
relating to a nonrecurring loss incurred in 2000) as a
percentage of net revenues increased to 34% for the quarter
ended March 31, 2002, from 28% for the comparable period in
2001.

GROWTH STRATEGY

Key elements of our growth strategy include the following:

o INTERNAL GROWTH. Due to our de novo strategy, we believe we
have not yet realized the full deposit and asset generation
potential in the communities now served by our existing
banking facilities. We believe we can leverage our existing
infrastructure to support additional business while
maintaining a high level of personalized customer service and
responsiveness. As consolidation in the financial services
industry continues, management expects that more individuals
and small businesses will become disenchanted with the
perceived lower level of service offered by the larger
institutions, providing continuing market share opportunity
for

us. We may from time to time compete for deposits,
particularly in our newer markets, with aggressive pricing,
which may reduce our net interest margin. With management's
focus on balancing further asset growth with earnings growth,
our current strategy is to continue less aggressive deposit
pricing at those banks with significant market share and more
established customer bases.

As a result of our acquisition of the Wayne Hummer Companies,
we expect certain customer funds currently invested in money
market mutual funds at the Wayne Hummer Companies to become
deposits of our banks. We plan to begin soliciting these
deposits beginning about the end of the second quarter of
2002. We estimate that approximately $200 to $300 million may
migrate from the mutual funds into deposit accounts of the
banks by the end of 2002. This migration of funds to the banks
is subject to the desire of the customers to make the
transition of their funds into FDIC insured bank accounts, our
capital capacity and the availability of suitable investments
in which to deploy the funds. Pending reinvestment of these
funds in loans or other higher-yielding earning assets, we
plan to invest the deposit funds in assets suitable for bank
investment.

o EXPANDING INTO ATTRACTIVE MARKETS WITH LIMITED LOCAL BANKING
COMPETITION. We plan to continue our geographic expansion by
leveraging our existing banks and opening new branch
facilities in nearby communities where management believes
targeted customers would be attracted to a community banking
alternative. Consistent with this strategy, in 2001 we opened
two new locations. In February 2001, we opened a new branch of
Crystal Lake Bank in McHenry, Illinois, and in September 2001,
we opened Hoffman Estates Community Bank, a branch of
Barrington Bank. Additionally, in January 2002 we opened a new
branch of Hinsdale Bank in Riverside, Illinois; in May 2002,
we opened a Highland Park, Illinois branch of Lake Forest
Bank; and we will soon be opening a permanent facility for our
Wauconda, Illinois branch of Libertyville Bank. We also intend
to continue the formation of additional de novo banks in
attractive markets in and around the Chicago metropolitan
area. We will continue to be impacted by start-up costs to the
extent we undertake additional de novo bank, branch and
business formations. In addition, we intend to explore and
consider potential acquisitions of other community banks that
are already operating in desirable markets. We believe some
banks may be attracted to our commitment to local operational
autonomy and may desire to provide their investors the
liquidity that could be offered by our publicly traded stock.
However, because of competition from other potential bidders
or seller price expectations, we may not be successful in
acquiring other banks at prices we consider attractive.

o AUGMENTING THE LOAN PORTFOLIO WITH OUR SPECIALTY LENDING
NICHES TO ALLOW THE BANKS TO MORE FULLY UTILIZE THEIR LENDING
CAPACITY AND ADDING RELATED FINANCIAL SERVICES BUSINESSES TO
INCREASE FEE INCOME. Our specialty lending niches have
enhanced the profitability of our community banks by
optimizing their earning asset base and allowing them to
diversify their loan portfolios. Certain of our related
financial services businesses also contribute to higher fee
income, such as administrative service fees earned by Tricom
for payroll processing. We may pursue acquisitions or
development of additional specialty lending businesses engaged
in asset generation suitable for bank investment and/or
secondary market sales. We may also pursue acquisitions or
development of related financial services businesses to
augment fee income. Management intends to continue to explore
various commercial and consumer finance activities and to seek
attractive potential acquisition candidates. Acquisitions, if
any, could have a short-term dilutive effect on earnings per
share.

o GROWTH OF TRUST AND INVESTMENT SERVICES PROVIDED TO SMALL AND
MID-SIZED BUSINESSES AND AFFLUENT INDIVIDUALS. With the
formation of Wayne Hummer Trust Company, formerly known as
Wintrust Asset Management, in 1998, we began to market trust
and investment services more aggressively to bank customers in
an effort to expand our market share and increase our fee
income. Due to its relatively small size and start-up nature,
our trust business segment was not yet profitable in 2001, but
our recent acquisition of the Wayne Hummer Companies has
significantly expanded our investment services customer base
and enables us to diversify our revenue stream. We expect that
higher brokerage and asset management fees will allow us to
increase noninterest income from 28% of total net revenues in
2001 to approximately 40% in 2002. We believe we can further
expand our trust and investment services business by marketing
our newly expanded base of brokerage and investment management
products and services to our banking clients while offering
trust services and estate planning products, as well as
traditional banking services, to brokerage and asset
management clients. We also expect to seek to recruit
additional investment professionals to staff our banking
locations. As a result, we may continue to experience higher
expense ratios in this segment as we integrate the Wayne
Hummer Companies into our business.

o UTILIZING THE INTERNET AS A NEW DISTRIBUTION CHANNEL FOR BOTH
EXISTING AND FUTURE BANK PRODUCTS AND SERVICES. We maintain
community bank websites and a number of on-line financial
services, including on-line banking, bill pay and check
register, investment portfolio review, home mortgage
applications, a community calendar, links to key sites and
wireless access. We anticipate adding new products and
services in the future, and expect that the Internet may
become an increasingly important distribution channel for our
banks. This will likely require continued investment to keep
pace with technological change.

OFFICE LOCATION

Our principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045-1951, and our telephone number is (847) 615-4096.

THE OFFERING

Common stock offered............................................... 1,185,000 shares

Offering price per share........................................... $28.70

Common stock to be outstanding after the offering.................. 16,935,605 shares(1)

Use of proceeds.................................................... We will use the net proceeds of this offering to
increase the capital at our existing banks to
pursue growth opportunities and for general
corporate purposes.

Risk Factors...................................................... See "Risk Factors" beginning on page 12 and
other information included in this prospectus for
a discussion of factors you should consider
carefully before deciding to invest in our
common stock.

Nasdaq National Market symbol..................................... WTFC

------------------------------------
(1) The number of shares shown to be outstanding after the offering is based
on the number of shares of our common stock outstanding as of May 29,
2002, and does not include 4,346,395 shares reserved for issuance under
our stock option and other compensation plans or upon the exercise of
outstanding warrants. As of May 29, 2002, we had outstanding options to
purchase 2,812,207 shares and warrants to purchase 229,313 shares of our
common stock.

SUMMARY CONSOLIDATED FINANCIAL DATA

The summary consolidated financial data presented below as of or for
each of the years in the five-year period ended December 31, 2001, are derived
from our audited historical financial statements. The summary data presented
below as of or for the three-month periods ended March 31, 2002 and 2001, are
derived from unaudited consolidated financial statements. In our opinion, all
adjustments, consisting only of normal recurring adjustments, necessary for a
fair statement of results as of or for the three-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 our Annual Report on Form 10-K for the fiscal year ended
December 31, 2001, and our Quarterly Report on Form 10-Q for the quarter ended
March 31, 2002. Results for past periods are not necessarily indicative of
results that may be expected for any future period, and results for the
three-month period ended March 31, 2002 are not necessarily indicative of
results that may be expected for the entire year ending December 31, 2002.

THREE MONTHS ENDED
MARCH 31, YEARS ENDED DECEMBER 31,
------------------- -------------------------------------------------------
2002(1) 2001 2001 2000 1999 1998 1997
------- ---- ---- ---- ---- ---- ----
(IN THOUSANDS, EXCEPT PER SHARE AMOUNTS)

STATEMENT OF INCOME
DATA:
Total interest income...... $41,971 $41,782 $166,455 $148,184 $109,331 $87,979 $65,111
Total interest expense..... 19,803 24,506 92,441 87,184 61,597 51,215 38,339
------- ------- -------- -------- -------- ------- -------
Net interest income........ 22,168 17,276 74,014 61,000 47,734 36,764 26,772
Provision for loan losses.. 2,348 1,638 7,900 5,055 3,713 4,297 3,404
------- ------- -------- -------- -------- ------- -------
Net interest income after
provision for loan
losses................... 19,820 15,638 66,114 55,945 44,021 32,467 23,368

Non-interest Income:
Gain on sale of premium
finance receivables..... 766 942 4,564 3,831 1,033 -- --
Fees on mortgage loans
sold................. 2,017 1,524 7,831 2,911 3,206 5,569 2,341
Trust, asset management
and brokerage fees.. 4,570 450 1,996 1,971 1,171 788 626
Service charges on
deposit accounts..... 738 547 2,504 1,936 1,562 1,065 724
Administrative services
revenues............ 822 1,021 4,084 4,402 996 -- --
Premium finance
defalcation-partial
settlement(2)........ 1,250 -- -- -- -- -- --
Securities (losses)
gains, net........... (215) 286 337 (40) 5 -- 111
Other................... 2,804 2,080 7,482 3,295 1,835 653 1,142
------- ------- -------- -------- -------- ------- -------
Total non-interest
income(2).......... 12,752 6,850 28,798 18,306 9,808 8,075 4,944
------- ------- -------- -------- -------- ------- -------
(See footnotes on page 11)

Non-interest Expense:
Salaries and
employee benefits $ 13,362 $ 8,478 $ 35,628 $ 28,119 $ 20,808 $ 18,944 $ 14,204
Equipment expense..... 1,730 1,484 6,297 5,101 3,199 2,221 1,713
Occupancy expense,
net................ 1,544 1,244 4,821 4,252 2,991 2,435 1,896
Data processing....... 1,014 830 3,393 2,837 2,169 1,676 1,337
Advertising and
marketing.......... 524 307 1,604 1,309 1,402 1,612 1,309
Professional fees..... 611 531 2,055 1,681 1,203 1,654 1,343
Amortization of
intangibles........ 17 178 685 713 251 120 100
Premium finance
defalcation(2)..... -- -- -- 4,320 -- -- --
Other non-interest
expenses........... 3,877 2,919 11,300 9,471 7,655 7,171 5,352
---------- --------- ---------- ---------- ---------- ---------- ----------
Total
non-interest
expense(2)....... 22,679 15,971 65,783 57,803 39,678 35,833 27,254
---------- --------- ---------- ---------- ---------- ---------- ----------
Income before taxes
and cumulative
effective of
accounting change..... 9,893 6,517 29,129 16,448 14,151 4,709 1,058
Income tax expense
(benefit)............. 3,531 2,359 10,436 5,293 4,724 (1,536) (3,788)
---------- --------- ---------- ---------- ---------- ---------- ----------
Income before
cumulative effect
of accounting change.. 6,362 4,158 18,693 11,155 9,427 6,245 4,846
Cumulative effect of
change in accounting
for derivatives, net
of tax................ -- (254) (254) -- -- -- --
---------- --------- ---------- ---------- ---------- ---------- ----------
Net income............ $ 6,362 $ 3,904 $ 18,439 $ 11,155 $ 9,427 $ 6,245 $ 4,846
========== ========= ========== ========== ========== ========== ==========

COMMON SHARE DATA:
Earnings per share:
Basic................. $ 0.42 $ 0.30 $ 1.34 $ 0.85 $ 0.76 $ 0.51 $ 0.42
Diluted............... 0.40 0.29 1.27 0.83 0.73 0.49 0.40
Cash dividends per
common share(3)....... 0.060 0.047 0.093 0.067 -- -- --
Book value per share..... 10.41 8.19 9.72 7.92 7.06 6.15 5.65
Weighted average common
shares outstanding:
Basic................. 15,078 12,923 13,734 13,066 12,373 12,212 11,633
Diluted............... 15,991 13,377 14,545 13,411 12,837 12,742 12,129
SELECTED FINANCIAL
CONDITION DATA (AT
END OF PERIOD):
Total assets............. $2,955,153 $2,166,630 $2,705,422 $2,102,806 $1,679,382 $1,348,048 $1,053,400
Total loans.............. 2,167,550 1,625,979 2,018,479 1,547,596 1,270,126 974,031 702,700
Total deposits........... 2,417,315 1,916,756 2,314,636 1,826,576 1,463,622 1,229,154 917,701
Notes payable............ 66,125 38,875 46,575 27,575 8,350 -- 20,402
Long term debt - trust
preferred securities 51,050 51,050 51,050 51,050 31,050 31,050 --
Total shareholders'
equity................ 163,521 105,872 141,278 102,276 92,947 75,205 68,790

(See footnotes on following page)

SELECTED FINANCIAL
RATIOS AND OTHER DATA:
Performance Ratios:
Net interest
margin(4)(5)(6)... 3.48% 3.67% 3.49% 3.66% 3.54% 3.43% 3.41%
Core net interest
margin(4)(6)(7)... 3.68 3.94 3.73 3.91 3.75 3.50 3.41
Net interest
spread(4)(6)(8)... 3.15 3.26 3.08 3.29 3.23 3.00 2.92
Non-interest income
to average
assets(4)......... 1.84 1.32 1.24 0.99 0.66 0.69 0.58
Non-interest expense
average to
assets(2)(4)...... 3.28 3.07 2.83 3.12 2.65 3.04 3.18
Net overhead
ratio(2)(4)(9).... 1.43 1.75 1.59 2.13 2.00 2.36 2.60
Efficiency
ratio(2)(10)...... 64.2 66.4 63.7 66.9 68.6 77.5 86.0
Return on average
assets(2)(4)...... 0.92 0.75 0.79 0.60 0.63 0.53 0.56
Return on average
equity(2)(4)...... 17.12 15.39 15.24 11.51 11.58 8.68 7.88
Average
loan-to-average
deposit ratio..... 89.8 87.1 87.4 87.7 86.6 80.1 80.1
Dividend payout
ratio(3)(4)....... 7.5 8.0 7.4 8.0 -- -- --
Asset Quality Ratios:
Non-performing
loans to total
loans............. 0.53% 0.86% 0.64% 0.63% 0.55% 0.56% 0.60%
Allowance for loan
losses to:
Total loans....... 0.68 0.68 0.68 0.67 0.69 0.72 0.73
Non-performing
loans........... 128.07 79.35 105.63 107.75 126.10 129.66 121.64
Net charge-offs to
average
loans(2)(4)....... 0.26 0.25 0.26 0.24 0.19 0.28 0.31
Non-performing assets
to total assets... 0.39 0.64 0.48 0.46 0.41 0.45 0.40
Other data at end of
period:
Number of banking
facilities........ 30 29 29 28 24 21 17

------------------------------------
(1) We completed our acquisition of the Wayne Hummer Companies effective as
of February 1, 2002. The results for the quarter ended March 31, 2002
include the results of the Wayne Hummer Companies since February 1,
2002.
(2) In 2000, we recorded a $4.3 million pre-tax charge ($2.6 million
after-tax) related to a fraudulent loan scheme perpetrated against our
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, we recovered $1.25 million
(pre-tax) of this amount ($754,000 after-tax).
(3) We declared our first semi-annual dividend payment in January 2000.
Dividend data reflected for the interim periods reflect semi-annual, not
quarterly, dividends.
(4) Certain financial ratios for interim periods have been annualized.
(5) Net interest income divided by average interest-earning assets.
(6) Calculated on a tax-equivalent basis.
(7) Core net interest margin excludes the interest expense associated with
the trust preferred securities.
(8) Yield earned on average interest-earning assets less rate paid on
average interest-bearing liabilities.
(9) Non-interest expense less non-interest income divided by average total
assets.
(10) Non-interest expense (excluding non-recurring items) divided by the sum
of net interest income on a tax equivalent basis plus non-interest
income (excluding securities gains and losses).

RISK FACTORS

You should carefully consider the following risk factors before you
decide to buy our common stock. You should also consider the other information
in this prospectus, as well as the documents incorporated by reference in this
prospectus.

DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY.

Our historical results have been impacted by our strategy of de novo
bank formations and branch openings. We have employed this strategy to build an
infrastructure that management believes can support additional internal growth
in our banks' respective markets. To expand into additional communities in and
around Chicago, we may undertake additional de novo bank formations or branch
openings. Based on our experience, 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 we have 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 we undertake additional de novo bank, branch and business formations, our
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
we are likely to continue to experience the effects of higher expenses relative
to operating income from the new operations. These expenses may be higher than
we expect or than our experience has shown. For example, Wayne Hummer Trust
Company, which we formed on September 30, 1998, as Wintrust Asset Management, is
not yet operating profitably.

WE MAY NOT BE ABLE TO SUCCESSFULLY IMPLEMENT OUR GROWTH STRATEGY.

Although we have historically grown primarily through de novo bank
formations and the establishment of new branch offices, our strategic plan also
includes potential acquisitions of other financial institutions in attractive
markets, trust and investment management services companies such as our recent
acquisition of the Wayne Hummer Companies and specialty lending or related
financial services businesses that offer unique earning asset niches or fee
income. We may not be successful in implementing our strategy for any number of
reasons, many beyond our control, including the following:

o if we are unable to identify attractive markets, locations or
opportunities, including attracting the necessary management,
to expand in the future, whether through de novo bank
formations, the addition of branch facilities or through
acquisitions of other community banks, specialty financial
services companies or fee-based businesses;

o if potential acquisitions are not available on terms
acceptable or favorable to us;

o if we are unable to obtain the required regulatory approvals
for any proposed acquisitions; or

o if we are unable to successfully integrate, operate and manage
any business that we acquire, including the Wayne Hummer
Companies.

WE DEPEND ON OUR ABILITY TO ATTRACT AND RETAIN KEY PERSONNEL; WE
RELY HEAVILY ON OUR MANAGEMENT TEAM, AND THE UNEXPECTED LOSS OF KEY MANAGERS MAY
ADVERSELY AFFECT OUR OPERATIONS.

Our success to date has been influenced strongly by our ability to
attract and to retain senior management experienced in banking and financial
services. Our ability to retain our executive officers

and the current senior management teams of each of our banks, First Insurance,
Tricom, Wayne Hummer Trust Company and the Wayne Hummer Companies, will continue
to be critical to the successful implementation of our strategies. We have
entered into employment contracts with four of our executive officers, including
Edward J. Wehmer, our President and Chief Executive Officer, David A. Dykstra,
our Senior Executive Vice President, Chief Operating Officer and Chief Financial
Officer, Robert F. Key, our Executive Vice President-Marketing, and Lloyd M.
Bowden, our Executive Vice President-Technology, as well as with approximately
48 of those senior officers who we consider to be key employees. It is also
important as we grow to be able to attract and retain additional qualified
senior and middle management. We do not currently maintain key-man life
insurance policies. The unexpected loss of services of any key management
personnel, or the inability to recruit and retain qualified personnel in the
future, could have an adverse effect on our business and financial results.

OUR ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB LOSSES THAT
MAY OCCUR IN OUR LOAN PORTFOLIO.

Our allowance for loan losses is established in consultation with
management of our operating subsidiaries and is maintained at a level considered
adequate by management to absorb loan losses that are inherent in the
portfolios. The amount of future losses is susceptible to changes in economic,
operating and other conditions, including changes in interest rates, that may be
beyond our 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 our 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 our 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.

OUR PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND COULD EXPOSE
US TO SIGNIFICANT LOSSES.

Of our total loans at March 31, 2002, 19% are comprised of commercial
insurance premium finance receivables that we generate through First Insurance.
These loans, intended to enhance the average yield of earning assets of our
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 is
less than $30,000.

Because we conduct 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 our banks. We may also be more
susceptible to third party fraud. Acts of fraud are difficult to detect and
deter, and we cannot assure investors that our risk management procedures and
controls will prevent losses from fraudulent activity. For example, in the third
quarter of 2000, we 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
we have since enhanced our internal control system at First Insurance, we may
continue to be exposed to the risk of significant loss in our premium finance
business.

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

party. We have recognized gains on the sales of the receivables, and the
proceeds of sales have provided us with additional liquidity. Consistent with
our strategy to be asset driven, we expect to pursue similar sales of premium
finance receivables in the future; however, we cannot assure you that there will
continue to be a market for sale of these loans and the extent of our future
sales of these loans will depend on the level of new volume growth in relation
to our capacity to retain the loans within our subsidiary banks' loan
portfolios. Because we have a recourse obligation to the purchaser of premium
finance loans that we sell, we 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
our estimate of losses at the time of sale.

OUR STRATEGY OF PURSUING SPECIALTY LENDING NICHES MAY EXPOSE US TO CREDIT RISKS
THAT ARE UNIQUE FOR A COMMUNITY BANKING ORGANIZATION OF OUR SIZE.

At March 31, 2002, 34% of our total loan portfolio consisted of loans
we make in what we consider to be specialty lending niches. In addition to our
premium finance loans, we engage in indirect auto lending, accounts receivable
financing, mortgage broker warehouse lending, and to a much lesser extent,
medical and municipal equipment leasing, loans to condominium, homeowner and
community associations, and small aircraft lending.

Our portfolio of automobile loans are originated indirectly through
unaffiliated automobile dealers located throughout the Chicago metropolitan
area. At March 31, 2002, our indirect auto loans were $184.4 million and
comprised approximately 9% of our loan portfolio. Because we are lending through
third-party originators, our indirect auto portfolio may be relatively riskier
than direct consumer lending. Also, because the indirect auto loan industry is
highly competitive, the cost of collection and repossession of the underlying
collateral may significantly reduce the profitability of this portfolio,
particularly in a recessionary environment.

Through Tricom we finance payrolls of companies engaged in the
temporary staffing business. At March 31, 2002, these finance receivables
totaled $17.6 million and represented approximately 1% of our loan portfolio.
The principal source of repayments on the loans we make in this niche are
payments to our borrowers from their customers who are located throughout the
United States. While we employ lockboxes and other cash management techniques to
protect our interests, to the extent third parties fail to pay or fraudulently
engage in the conversion of funds through misuse or nonuse of the lockbox or the
creation of ghost payrolls, we may suffer losses.

Our lease financing niche may involve a higher degree of credit risk
than mortgage or consumer lending due primarily to the potential for relatively
rapid depreciation of medical equipment and other assets securing leases.
Similarly, in the event of a default of loans originated in our aircraft lending
program, the marketability of the collateral may make it more difficult to
convert this collateral to cash, especially in an adverse economic environment.
In our condominium and homeowner association lending niche, we may face
difficulties in securing repayment from our association borrowers to the extent
they are unable to collect assessments from their members, and we may suffer
losses if we are unable to enforce liens against homeowner properties.

OUR ASSET MANAGEMENT AND BROKER-DEALER BUSINESSES MAY BE AFFECTED BY
FLUCTUATIONS IN THE TRADING VOLUME AND PRICE LEVELS OF SECURITIES AND WE MAY BE
ADVERSELY AFFECTED BY A DOWNTURN IN THE U.S. SECURITIES MARKET.

The results of our brokerage and asset management subsidiaries depends
heavily on conditions in the financial markets and on economic conditions
generally, both domestically and abroad. Because a

significant portion of our revenue in these businesses is derived from
commissions, margin interest revenue and principal transactions, a decline in
stock prices, trading volumes or liquidity could result in the failure of buyers
and sellers of securities to fulfill their settlement obligations, and in the
failure of our brokerage clients to fulfill their credit obligations, which
would adversely affect our profitability.

We often permit our brokerage clients to purchase securities on margin
or, in other words, to borrow a portion of the purchase price from us and
collateralize the loan with a set percentage of the securities. During steep
declines in securities prices, the value of the collateral securing margin
purchases may drop below the amount of the purchaser's indebtedness. If a client
is unable to provide additional collateral for these loans, we may lose money on
these margin transactions. In addition, particularly during market downturns, we
may face additional expense defending or pursuing claims or litigation.

Many factors outside our control may directly affect the securities and
investment management industries, in many cases in an adverse manner. These
include economic and political conditions, broad trends in business and finance,
legislation and regulation affecting the national and international financial
communities, inflation, currency values, the level and volatility of interest
rates, market conditions, the availability and cost of short-term or long-term
funding and capital, and the credit capacity or perceived credit worthiness of
the securities industry in the marketplace.

WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

Our earnings are derived from the operations of our subsidiaries, and
we are principally dependent on net interest income, calculated as the
difference between interest earned on loans and investments and the interest
expense paid on deposits and other borrowings. Our 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
we have 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. If market interest rates should
move contrary to our "gap" position on interest earning assets and interest
bearing liabilities, the "gap" will work against us and our net interest income
may be negatively affected. The success of our covered call option strategy may
also be affected by changes in interest rates. With the decline in interest
rates over the last year to historically low levels, we have been able to
augment the total return of our investment securities portfolio by selling call
options on fixed-income securities we own. We recorded fee income of $4.3
million during 2001 and $1.6 million during the first quarter of 2002 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 we earn on these transactions will likely decline.

OUR FUTURE SUCCESS IS DEPENDENT ON OUR ABILITY TO COMPETE EFFECTIVELY IN THE
HIGHLY COMPETITIVE BANKING INDUSTRY.

The financial services business is highly competitive, and we encounter
strong direct competition for deposits, loans and other financial services in
all of our market areas. Our principal competitors include other commercial
banks, savings banks, savings and loan associations, mutual funds, money market
funds, finance companies, trust companies, insurers, leasing companies, credit
unions, mortgage companies, private issuers of debt obligations and suppliers of
other investment alternatives, such as securities firms. Many of our non-bank
competitors are not subject to the same degree of regulation as that imposed on
bank holding companies, federally insured banks and national or Illinois
chartered banks. As a result, such non-bank competitors have advantages over us
in providing certain services. In recent years, several major multi-bank holding
companies have entered or expanded in the Chicago metropolitan

market. Generally, these financial institutions are significantly larger than we
are and have greater access to capital and other resources. Our ability to
compete effectively in the marketplace is also dependent on our ability to adapt
successfully to technological changes within the banking and financial services
industries.

OUR BUSINESS MAY BE ADVERSELY AFFECTED BY THE HIGHLY REGULATED ENVIRONMENT IN
WHICH WE OPERATE.

We are subject to extensive federal and state legislation, regulation
and supervision. Recently enacted, proposed and future banking legislation and
regulations have had, will continue to have or may have a significant impact on
the financial services industry. Some of the legislative and regulatory changes
may increase our costs of doing business and, as a result, advantage our
competitors who may not be subject to similar legislative and regulatory
requirements. In addition, self regulatory organizations, such as the New York
Stock Exchange and the National Association of Securities Dealers, require our
securities brokerage subsidiaries to comply with their extensive rules and
regulations, and we could be adversely affected by applicable changes in such
legislation and regulation.

SINCE OUR BUSINESS IS CONCENTRATED IN THE CHICAGO METROPOLITAN AREA, A DOWNTURN
IN THE CHICAGO ECONOMY MAY ADVERSELY AFFECT OUR BUSINESS.

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

FUTURE SALES OF OUR COMMON STOCK OR OTHER SECURITIES MAY DILUTE THE VALUE OF THE
COMMON STOCK.

Our board of directors has the authority, without action or vote of the
shareholders, to issue all or part of any authorized but unissued shares of our
common stock and preferred stock, including common shares authorized to be
issued under our stock option plan, shares that employees may purchase at their
election pursuant to our Employee Stock Purchase Plan and shares that may be
issuable to our directors as compensation for attendance at Board meetings
pursuant to our Directors Deferred Fee and Stock Plan. In the future, we may
also issue additional securities, through public or private offerings, in order
to raise additional capital to support our growth or in connection with possible
acquisitions. Future issuances will dilute the percentage of ownership interest
of shareholders and may dilute the per share book value of the common stock. In
addition, option holders may exercise their options at a time when we would
otherwise be able to obtain additional equity capital on more favorable terms.

OUR ABILITY TO PAY DIVIDENDS ON OUR COMMON STOCK IS LIMITED BY LAW AND CONTRACT.

Our ability to pay dividends on our common stock largely depends on our
receipt of dividends from our banks. The amount of dividends that our banks may
pay to us is limited by federal and state banking laws and regulations. We
registered as a financial holding company in connection with our acquisition of
the Wayne Hummer Companies, and, as a result, our banks are now required to
maintain capital sufficient to meet the "well-capitalized" standards set by the
regulators and will be able to pay dividends to us only so long as their capital
continues to exceed these levels. We or our banks may decide to limit the
payment of dividends even when we or they have the legal ability to pay them in
order to retain earnings for use in our or our banks' business. We are also
prohibited from paying dividends on our common stock if we have not made
distributions or required payments on our outstanding trust preferred securities
and debt securities.

THERE IS A LIMITED TRADING MARKET FOR OUR COMMON STOCK; YOU MAY NOT BE ABLE TO
RESELL YOUR SHARES AT OR ABOVE THE PRICE YOU PAY FOR THEM.

The price of our shares of common stock subject to this offering may be
greater than the market price for our common stock following the offering. The
price of our common stock has been, and will likely continue to be, subject to
fluctuations based on, among other things, economic and market conditions for
financial services companies and the stock market in general, as well as changes
in investor perceptions of our company.

Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The development and maintenance of an active public trading
market depends, however, upon the existence of willing buyers and sellers, the
presence of which is beyond our control or the control of any market maker.
While we are a publicly traded company, the volume of trading activity in our
stock is relatively limited. Even if a more active market develops, there can be
no assurance that such a market will continue, or that our shareholders will be
able to sell their shares at or above the offering price. All of the 762,734
shares of our common stock issued in connection with the acquisition of the
Wayne Hummer Companies, as well as certain other shares, are covered by resale
registration statements and some of these shares have not yet been sold. These
remaining shares can be freely sold from time to time in the market. The market
price of our common stock could drop significantly if shareholders sell or are
perceived by the market as intending to sell large blocks of our shares.

OUR SHAREHOLDER RIGHTS PLAN AND PROVISIONS IN OUR ARTICLES OF INCORPORATION AND
OUR BY-LAWS MAY DELAY OR PREVENT AN ACQUISITION OF US BY A THIRD PARTY.

Our board of directors has implemented a shareholder rights plan. The
rights, which are attached to our shares and trade together with our 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 our
shares without negotiating with our board of directors or to launch a proxy
contest or to acquire control of a larger block of our shares. If triggered, the
rights will cause substantial dilution to a person or group that attempts to
acquire us without approval of our 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 incumbent directors and key management. In addition,
our executive officers may be more likely to retain their positions with us as a
result of the plan, even if their removal would be beneficial to shareholders
generally.

Our articles of incorporation and our by-laws contain provisions,
including a staggered board provision, that make it more difficult for a third
party to gain control or acquire us without the consent of our 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 our 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 our shareholders.

USE OF PROCEEDS

Our net proceeds from the sale of 1,185,000 shares of our common stock
in this offering are estimated to be approximately $31.7 million after deducting
the underwriting discount and aggregate offering expenses payable by us. The
offering expenses are estimated to be approximately $250,000. If the
underwriters' over-allotment option is exercised in full, the net proceeds will
be approximately $36.5 million.

We will use the net proceeds of this offering to increase the capital
at our existing banks to pursue growth opportunities and for general corporate
purposes.

CAPITALIZATION

The following table sets forth our total indebtedness and
capitalization at March 31, 2002, on an historical basis and as adjusted for the
offering (assuming no exercise of the underwriters' over-allotment option) as if
such sale had been consummated on March 31, 2002. This data should be read in
conjunction with the consolidated financial statements and notes thereto
incorporated by reference into this prospectus from our Annual Report on Form
10-K for the fiscal year ended December 31, 2001, and from our Quarterly Report
on Form 10-Q for the quarter ended March 31, 2002.

MARCH 31, 2002
------------------------
ACTUAL AS ADJUSTED
------ -----------
(DOLLARS IN THOUSANDS)

INDEBTEDNESS:
Other borrowings (including securities sold under agreement to repurchase,
federal funds purchased and Federal Home Loan Bank advances)................. $203,624 $203,624
Notes payable under revolving credit line with an unaffiliated commercial bank.. 66,125 66,125
Long-term debt--trust preferred securities....................................... 51,050 51,050
-------- --------
Total indebtedness........................................................... 320,799 320,799
-------- --------

SHAREHOLDERS' EQUITY:
Preferred stock, no par value; 20,000,000 shares authorized, of which 100,000
shares are designated Junior Serial Preferred Stock A; no shares
issued and outstanding....................................................... -- --
Common stock, no par value; 30,000,000 shares authorized; 15,711,641 shares
issued and outstanding; 16,896,641 shares issued and outstanding as adjusted. 15,712 16,897
Surplus......................................................................... 116,201 146,737
Common stock warrants to acquire 231,209 shares(1).............................. 98 98
Retained earnings............................................................... 36,482 36,482
Accumulated other comprehensive loss............................................ (4,972) (4,972)
-------- --------
Total shareholders' equity................................................... 163,521 195,242
-------- --------
Total capitalization......................................................... $484,320 $516,041
======== ========

CAPITAL RATIOS:
Leverage ratio(2)............................................................... 7.0% 8.1%
Tier 1 capital ratio............................................................ 7.6 8.9
Total risk based capital ratio.................................................. 8.2 9.5

------------------------------------
(1) The warrants are exercisable at prices ranging from $9.90 to $10.00 per
share and expire between December 2002 and November 2005.
(2) The leverage ratio is Tier 1 capital divided by average quarterly
assets, after deducting intangible assets and net deferred tax assets in
excess of regulatory maximum limits.

PRICE RANGE OF COMMON STOCK AND DIVIDEND POLICY

Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The following table sets forth the high and low sales prices
reported on the Nasdaq National Market for our common stock for the periods
indicated and the semi-annual dividends paid by us during such periods. The
following information gives effect to a 3-for-2 stock split effective as of
March 14, 2002.

HIGH LOW DIVIDEND
---- --- --------
2000
----
First Quarter....................... $10.67 $ 8.92 $0.0333
Second Quarter...................... 10.83 9.17 --
Third Quarter....................... 11.88 10.17 0.0333
Fourth Quarter...................... 11.33 10.25 --

2001
----
First Quarter....................... $12.75 $10.54 $0.0467
Second Quarter...................... 17.62 11.67 --
Third Quarter....................... 21.41 16.27 0.0467
Fourth Quarter...................... 22.13 17.93 --

2002
----
First Quarter....................... $22.99 $18.33 $0.0600
Second Quarter (through June 10).... 29.30 22.22 --

As of May 29, 2002, there were 1,245 shareholders of record of our
common stock.

COMMON STOCK DIVIDEND POLICY

In January 2000, our board of directors approved the payment of our
first semi-annual cash dividend on our common stock. We have continued to pay a
semi-annual cash dividend since that time. The final determination of timing,
amount and payment of dividends on our common stock is at the discretion of our
board of directors and will depend upon our profitability, financial condition,
capital requirements and other relevant factors, including the restrictions
described below.

Because the principal source of our income at the holding company level
is dividends from our banks, our ability to pay dividends on common stock is
dependent on the banks' ability to pay dividends to us. The payment of dividends
by the banks is subject to certain restrictions imposed by federal and state
banking laws and regulations. During 2001 and 2000, our banks paid us dividends
of $13.5 million and $16.0 million, respectively. During 1999, the banks paid no
dividends. De novo banks are prohibited from paying dividends during the first
three years of operations. Currently, Northbrook Bank, which began operations in
November 2000, is our only bank subject to this dividend restriction; this
restriction will lapse in November 2003.

Our ability to pay cash dividends on our common stock is also subject
to statutory restrictions and restrictions arising under the terms of our
outstanding and any future debt securities and trust preferred securities. The
terms of such securities generally restrict payment of dividends on common stock
until required payments and distributions are made on those securities and may
impose additional restrictions in the future. Under applicable corporate law, we
are permitted to pay dividends only to the extent of our shareholders' equity.
Federal regulation of bank holding companies may also impose restrictions on the
ability of a bank holding company to pay dividends.

UNDERWRITING

Subject to the terms and conditions set forth in the underwriting
agreement, the underwriters named below have severally agreed to purchase from
us an aggregate of 1,185,000 shares of common stock in the amount set forth
opposite their respective names.

NUMBER OF
UNDERWRITERS SHARES
------------ ------
RBC Dain Rauscher Inc................................... 412,300
U.S. Bancorp Piper Jaffray Inc......................... 282,100
Stifel, Nicolaus & Company, Incorporated............... 282,100
Raymond James & Associates, Inc........................ 108,500
Advest, Inc............................................ 50,000
Howe Barnes Investments, Inc........................... 50,000
---------
Total............................................... 1,185,000
=========

The underwriting agreement provides that the underwriters' obligations
are subject to specified conditions precedent and that the underwriters are
committed to purchase all of the shares of our common stock offered hereby if
the underwriters purchase any of such shares of common stock.

The underwriters have advised us that they propose to offer the shares
of common stock to the public at the public offering price set forth on the
cover page of this prospectus and to selected dealers at such price less a
concession not in excess of $1.00 per share. The underwriters may allow and such
dealers may reallow a discount not in excess of $0.10 per share to certain other
brokers and dealers. After the offering, the public offering price, concession,
discount and other selling terms may be changed by the underwriters.

We have granted to the underwriters an option, exercisable for 30 days
after the date of this prospectus, to purchase up to 177,750 additional shares
of our common stock solely to cover over-allotments, if any, at the same price
per share to be paid by the underwriters for the other shares of common stock
offered hereby.

The underwriters' commissions are shown in the following table. These
amounts are shown assuming both no exercise and full exercise of the
underwriters' option to purchase additional shares of common stock.

NO EXERCISE FULL EXERCISE
----------- -------------
Per share....................................... $ 1.72 $ 1.72
Total........................................... $2,038,200 $2,343,930

In connection with the offering of the shares of our common stock, the
underwriters and any selling group members and their respective affiliates may
engage in transactions effected in accordance with Rule 104 of the SEC's
Regulation M that are intended to stabilize, maintain or otherwise affect the
market price of the shares of our common stock. Such transactions may include
over-allotment transactions in which an underwriter creates a short position for
its own account by selling more shares of our common stock than it is committed
to purchase from us. In such a case, to cover all or part of the short position,
the underwriters may purchase shares of our common stock in the open market
following completion of the initial offering of the shares of our common stock.
The underwriters also may engage in stabilizing transactions in which they bid
for, and purchase, shares of our common stock at a level above that which might
otherwise prevail in the open market for the purpose of preventing or retarding
a decline in the market price of the shares of our common stock. The
underwriters may also reclaim any

selling concession allowed to a dealer if the underwriters repurchase shares
distributed by that dealer. Any of the foregoing transactions may result in the
maintenance of a price for the shares of our common stock at a level above that
which might otherwise prevail in the open market. Neither we nor the
underwriters makes any representation or prediction as to the direction or
magnitude of any effect that the transactions described above may have on the
price of the shares of our common stock. The underwriters are not required to
engage in any of the foregoing transactions and, if commenced, such transactions
may be discontinued at any time without notice. These transactions may be
effected on the Nasdaq National Market, in the over-the-counter market or
otherwise.

In connection with this offering, some underwriters may also engage in
passive market making transactions in our common stock on the Nasdaq National
Market. Passive market making consists of displaying bids on the Nasdaq National
Market limited by the prices of independent market makers and effecting
purchases limited by those prices in response to order flow. Rule 103 of
Regulation M promulgated by the SEC limits the amount of net purchases that each
passive market maker may make and the displayed size of each bid. Passive market
making may stabilize the market price of our common stock at a level above that
which might otherwise prevail in the open market and, if commenced, may be
discontinued at any time.

We agreed to indemnify the underwriters and their controlling persons
against specified liabilities, including liabilities under the Securities Act of
1933, or to contribute to payments the underwriters may be required to make in
respect thereof.

We and our executive officers and directors have agreed for a period of
90 days after the date of this prospectus, we and they will not, without the
prior written consent of RBC Dain Rauscher Inc. on behalf of the underwriters,
directly or indirectly, (1) offer, pledge (except for pledges granted prior to
the date of this prospectus), sell, contract to sell, sell any option or
contract to purchase, purchase any option or contract to sell, grant any option,
right or warrant to purchase, lend or otherwise transfer or dispose of (subject
to some exceptions) any shares of our common stock, or any securities
convertible into, or exercisable or exchangeable for, our common stock (other
than approximately 441,000 shares with respect to which one of our directors
shares voting and investment power) or (2) enter into any swap or other
agreement that transfers, in whole or in part, any economic equivalent of
ownership of shares of our common stock.

We have agreed that, except pursuant to a publicly announced stock
repurchase program to purchase shares of our common stock or under our stock
option plan or employee stock purchase plan, we will not for a period of 180
days after the date of this prospectus, without the prior written consent of RBC
Dain Rauscher Inc. on behalf of the underwriters, purchase, redeem or call for
redemption, or prepay or give notice of prepayment (or announce any redemption
or call for redemption, or any prepayment or notice of prepayment) of, any of
our securities.

The underwriters have informed us that they do not intend to confirm
sales to any discretionary account without the prior written approval of the
customer in compliance with NASD Rule 2720(l).

TRANSFER AGENT

The transfer agent for our common stock is Illinois Stock Transfer
Company, 209 West Jackson Boulevard, Suite 903, Chicago, Illinois 60606.

LEGAL MATTERS

Certain legal matters relating to the common stock offered by this
prospectus, including the validity of the common stock, have been passed upon
for us by Vedder, Price, Kaufman & Kammholz, Chicago, Illinois. Certain legal
matters have been passed upon for the underwriters by Jones, Day, Reavis &
Pogue, Chicago, Illinois.

EXPERTS

Our consolidated financial statements incorporated by reference in our
Annual Report on Form 10-K for the year ended December 31, 2001, have been
audited by Ernst & Young LLP, independent auditors, as set forth in their report
thereon incorporated by reference in our Annual Report and in this prospectus.
These consolidated financial statements are incorporated by reference in this
prospectus in reliance upon the report given on the authority of Ernst & Young
LLP as experts in accounting and auditing.

WHERE YOU CAN FIND MORE INFORMATION

This prospectus is a part of a Registration Statement on Form S-3 that
we filed with the SEC under the Securities Act. This prospectus does not contain
all the information set forth in the registration statement, certain parts of
which are omitted in accordance with the rules and regulations of the SEC. For
further information with respect to us and the securities offered by this
prospectus, reference is made to the registration statement, including the
exhibits to the registration statement and the documents incorporated by
reference.

We file annual, quarterly and special reports, proxy statements and
other information with the SEC. Our filings are available to the public over the
Internet at the SEC's web site at http://www.sec.gov. You may also read and copy
any document we file with the SEC at its public reference facilities at 450
Fifth Street, N.W., Washington, D.C. 20549. You can also obtain copies of the
documents at prescribed rates by writing to the Public Reference Section of the
SEC at 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at
1-800-SEC-0330 for further information on the operation of the public reference
facilities. Our SEC filings are also available on our web site at
http://www.wintrust.com, and at the office of the Nasdaq National Market. For
further information on obtaining copies of our public filings at the Nasdaq
National Market, you should call (212) 656-5060.

DOCUMENTS INCORPORATED BY REFERENCE

We "incorporate by reference" into this prospectus the information we
file with the SEC, which means that we can disclose important information to you
by referring you to those documents. The information incorporated by reference
is an important part of this prospectus.

Some information contained in this prospectus updates and supersedes
the information incorporated by reference and some information that we file
subsequently with the SEC will automatically update this prospectus. We
incorporate by reference the documents listed below:

o our Annual Report on Form 10-K for the fiscal year ended
December 31, 2001, filed with the SEC on April 1, 2002 (File
No. 0-21923);

o our Quarterly Report on Form 10-Q for the quarter ended March
31, 2002, filed with the SEC

on May 15, 2002, as amended to provide additional exhibits by
our Form 10-Q/A filed with the SEC on June 7, 2002 (File No.
0-21923);

o our Current Report on Form 8-K dated January 17, 2002, filed
with the SEC on February 8, 2002 (File No. 0-21923);

o our Current Report on Form 8-K dated February 20, 2002, filed
with the SEC on February 22, 2002 (File No. 0-21923);

o our Current Report on Form 8-K dated April 19, 2002, filed
with the SEC on May 3, 2002 (File No. 0-21923); and

o the descriptions of (a) our Common Stock contained in our
Registration Statement on Form 8-A dated January 3, 1997 (File
No. 0-21923), and (b) the associated preferred share purchase
rights contained in our Registration Statement on Form 8-A
dated August 28, 1998 (File No. 0-21923).

We also incorporate by reference any filings we make with the SEC under
Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934 after
the initial filing of the first registration statement that contains this
prospectus and before the time that all of the shares offered by this prospectus
are sold.

You may request, either orally or in writing, and we will provide, a
copy of these filings at no cost by contacting David A. Dykstra, our Chief
Operating Officer, at the following address and phone number:

Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois 60045-1951
(847) 615-4096

1,185,000 SHARES