Filed Pursuant to Rule 424(b)(3)
                           Registration No. 333-84188

PROSPECTUS

                         WINTRUST FINANCIAL CORPORATION

                         912,734 SHARES OF COMMON STOCK


         Certain shareholders of Wintrust Financial Corporation are offering for
sale from time to time up to 912,734 shares of our common stock under this
prospectus. The selling shareholders may offer the shares:

         o        to or through one or more underwriters,

         o        directly to purchasers,

         o        on the Nasdaq National Market in typical brokerage
                  transactions,

         o        in negotiated transactions, or otherwise.

         The selling shareholders may sell the shares of common stock covered by
this prospectus:

         o        at market prices prevailing at the time of sale,

         o        at prices related to the then-prevailing market price, or

         o        at negotiated prices.

         We will not receive any proceeds from the sale of the shares of common
stock by the selling shareholders. No minimum purchase is required and no
arrangement has been made to have funds received by the selling shareholders
and/or any registered representatives placed in an escrow, trust or similar
account or arrangement.

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC." On May 30, 2002, the closing price of our common stock as
reported on Nasdaq was $28.80 per share.

         YOU SHOULD CONSIDER, AMONG OTHER THINGS, THE INFORMATION SET FORTH IN
"RISK FACTORS" BEGINNING ON PAGE 8 OF THIS PROSPECTUS.

         THE SHARES OF COMMON STOCK THAT ARE BEING OFFERED ARE NOT SAVINGS
ACCOUNTS OR DEPOSITS OR OTHER OBLIGATIONS OF A BANK AND ARE NOT INSURED BY THE
BANK INSURANCE FUND OR THE FEDERAL DEPOSIT INSURANCE CORPORATION OR ANY
GOVERNMENTAL AGENCY.

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


                  THE DATE OF THIS PROSPECTUS IS MAY 30, 2002.





                                TABLE OF CONTENTS

                                                                            PAGE

Summary Information............................................................1
Risk Factors...................................................................8
Use of Proceeds...............................................................14
Price Range of Common Stock and Dividend Policy...............................14
Selling Shareholders..........................................................15
Plan of Distribution..........................................................17
Transfer Agent................................................................18
Legal Matters.................................................................18
Experts  .....................................................................18
Where You Can Find More Information...........................................18
Documents Incorporated By Reference...........................................19


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

         You should rely only on the information provided or incorporated by
reference in this prospectus. We 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, these securities in any state where the offer or
sale is not permitted. The information in this prospectus is complete and
accurate as of the date on the front cover, but the information may have changed
since that date.

                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 8.

         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.

                                       i





                               SUMMARY INFORMATION

         This summary highlights information about Wintrust and our business and
should be read in conjunction with the documents incorporated by reference into
this prospectus. Because this is a summary, it may not contain all of the
information that is important to you. Therefore, you should also read the more
detailed information that is included in the documents incorporated by
reference, including our financial statements included in our Form 10-K report
for the year ended December 31, 2001, as well as the "Risk Factors" section of
this prospectus beginning on page 8, before making a decision to invest in our
common stock.

         This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 912,734 shares of common
stock. We newly issued 762,734 of these shares to the selling shareholders in
February 2002 in connection with our acquisition of the Wayne Hummer Companies.
We paid $28 million for the Wayne Hummer Companies, consisting of $8 million in
cash, 762,734 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. This
prospectus covers up to a total of 150,000 additional shares that we may issue
to the selling shareholders if they are eligible to receive these additional
purchase price amounts. Because the issuance of the shares in that transaction
was not registered with the SEC, the selling shareholders have "restricted
stock." All of the selling shareholders were former owners of the Wayne Hummer
Companies and each of them, other than Messrs. Kahlfeldt and Rogers, is
currently employed by us, pursuant to an employment agreement entered into in
connection with the transaction, as part of our asset management and securities
brokerage businesses. We are registering the shares to enable the selling
shareholders to resell the shares in the public market from time to time or on a
delayed basis and to permit secondary trading of the shares after they are sold
by the selling shareholders.

ABOUT WINTRUST FINANCIAL

         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 30 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.

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% 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 (collectively referred to in this prospectus as the Wayne Hummer
Companies), each based in Chicago. 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 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

                                       2





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.

                                       3





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 and productive 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%
                  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

                                       4





                  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 non-recurring 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
                  money market and time 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

                                       5





                  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

                                       6





                  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.

                                       7





                                  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 Trust 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

                                       8





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

                                       9





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 of $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

                                       10





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 could 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

                                       11





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.
Although currently the economy in the area is favorable, 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
became 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.

                                       12





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.

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.

                                       13





                                USE OF PROCEEDS

         We will not receive any of the proceeds from the sale of the shares of
common stock by the selling shareholders. We expect to incur expenses in
connection with this offering in the amount of approximately $30,000 for
registration, legal, accounting and miscellaneous fees and expenses. We will not
pay for expenses such as commissions and discounts of brokers, dealers or agents
or the fees and expenses of counsel, if any, for the selling shareholders. See
"Selling Shareholders" and "Plan of Distribution."

                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
                                              ----             ---            --------
                                                                      
2002
----
First Quarter.......................         $22.99           $18.33           $0.0600
Second Quarter (through May 30).....         $29.30           $22.22              --

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              --

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              --



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

                                       14





         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.

                              SELLING SHAREHOLDERS

         This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 912,734 shares of common
stock. We newly issued 762,734 of these shares to the selling shareholders in
February 2002 in payment of part of the $28 million purchase price in our
acquisition of the Wayne Hummer Companies. This prospectus also covers up to a
total of 150,000 additional shares that may be issuable to the selling
shareholders if they are eligible to receive additional purchase price amounts
that are contingent upon the future financial performance of the businesses
acquired. Because the issuance of the shares in that transaction was not
registered with the SEC, the selling shareholders have "restricted stock." All
of the selling shareholders were former owners of the Wayne Hummer Companies and
each of them, other than Messrs. Kahlfeldt and Rogers, is currently employed by
us, pursuant to an employment agreement entered into in connection with the
transaction, as part of our asset management and brokerage subsidiaries. Mr.
Kratzer, who holds the position of President and Chief Executive Officer of
Wayne Hummer Investments, also now serves as a member of our board of directors.
Messrs. Steven R. Becker, Kratzer and Wholey and Ms. Kogut serve as directors of
Wintrust Asset Management.

         We are registering the shares to enable the selling shareholders to
resell the shares in the public market from time to time or on a delayed basis
and to permit secondary trading of the shares after they are sold by the selling
shareholders. We are paying for the registration of such securities but will not
pay for the fees, commissions, and other similar expenses, if any, of the
selling shareholders, their attorneys or other representatives, as a result of
the sale of such securities by the selling shareholders. See "Use of Proceeds"
and "Plan of Distribution."

                                       15





         The following table sets forth, to the best of our knowledge,
information concerning the selling shareholders, the number of shares to be
offered and sold by the selling shareholders and the amount of common stock that
will be owned by the selling shareholders following the offering (assuming sale
of all shares of common stock being offered hereby).




                             NUMBER OF SHARES                           NUMBER OF SHARES      PERCENTAGE OF SHARES
                              OWNED PRIOR TO      NUMBER OF SHARES     TO BE OWNED AFTER       TO BE OWNED AFTER
   SELLING SHAREHOLDER           OFFERING         TO BE OFFERED(1)          OFFERING                OFFERING
   -------------------       ---------------      ----------------     -----------------      --------------------
                                                                                         
H. Flagg Baum.........            27,802               27,802                 --                     *
George T. Becker......            45,618               45,618                 --                     *
Linda C. Becker.......            40,027               40,027                 --                     *
Steven R. Becker......            49,867               49,867                 --                     *
Philip M. Bruno.......            26,908               26,908                 --                     *
W. Douglas Carroll....            50,836               50,836                 --                     *
Peder H. Culver.......            17,143               17,143                 --                     *
Mark H. Dierkes.......             7,453                7,453                 --                     *
Daniel G. Hack........            25,269               25,269                 --                     *
Philip W. Hummer......            48,078               48,078                 --                     *
William B. Hummer.....            41,965               41,965                 --                     *
Laura A. Kogut........            34,138               34,138                 --                     *
Richard J. Kosarek....            34,735               34,735                 --                     *
Raymond L. Kratzer....            51,880               51,880                 --                     *
Philip Scott Park.....            11,181               11,181                 --                     *
Joseph A. Piekarczyk..            39,432               39,432                 --                     *
David P. Poitras......            25,194               25,194                 --                     *
Thomas J. Rowland.....            30,114               30,114                 --                     *
Floyd E. Siegel.......            29,815               29,815                 --                     *
Ronald A. Tyrpin......            25,342               25,342                 --                     *
Laurence H. Weisz.....            23,851               23,851                 --                     *
Richard Wholey, Jr....            39,580               39,580                 --                     *
Jean E. Williams......            19,156               19,156                 --                     *
Robert F. Kahlfeldt...             2,922                2,922                 --                     *
William A. Rogers.....            14,428               14,428                 --                     *
                                 -------              -------            -------
   Total..............           762,734              762,734                 --                     *
                                 =======              =======            =======

------------------
*       Less than 1%
(1)     This prospectus also covers up to a total of 150,000 additional shares
        that may be issuable to the selling shareholders if they are eligible to
        receive additional purchase price amounts that are contingent upon the
        future financial performance of the businesses acquired.



                                       16





                              PLAN OF DISTRIBUTION

         The common stock offered by this prospectus may be offered and sold
from time to time by the selling shareholders. As used in this prospectus,
"selling shareholders" includes those individuals or entities who may have had
shares of common stock given to them as a gift by a named selling shareholder
after the date of this prospectus and any individuals or entities who may have
shares of common stock pledged to them as collateral by a named selling
shareholder after the date of this prospectus. See "Selling Shareholders." The
shares of common stock covered by this prospectus may be sold, from time to
time, by the selling shareholders in one or more types of transactions (which
may include block transactions) on Nasdaq, in the over-the-counter market, in
negotiated transactions, through put or call options transactions relating to
the shares of common stock, through short sales of shares of common stock, or a
combination of such methods of sale, or otherwise at prices and at terms then
prevailing or at prices related to the then current market price, or in
negotiated transactions. The shares of common stock may be sold by one or more
of the following methods: (a) a block trade in which the broker or dealer so
engaged will attempt to sell the shares of common stock as agent but may
position and resell a portion of the block as principal in order to facilitate
the transaction; (b) a purchase by a broker or dealer as principal, and the
resale by such broker or dealer for its account pursuant to this prospectus,
including resale to another broker or dealer; or (c) ordinary brokerage
transactions and transactions in which the broker solicits purchasers. Thus, the
period of distribution of these shares of common stock may occur over an
extended period of time.

         The selling shareholders may effect such transactions by selling the
shares of common stock directly to purchasers or to or through a broker or
dealer, who may act as an agent or principal. Such broker or dealer may receive
compensation in the form of discounts, concessions, or commissions from the
selling shareholders and/or the purchasers of shares of common stock for whom
such broker or dealer may act as agent or to whom he sells as principal, or both
(which compensation as to a particular broker or dealer might be in excess of
customary commissions). We know of no existing agreements, understandings or
arrangements between any selling shareholder, broker, dealer, underwriter or
agent relating to the sale or distribution of the shares of common stock.

         The selling shareholders will not pay any of the proceeds from the sale
of the shares of common stock to us. We expect to incur expenses in connection
with this offering in the amount of approximately $30,000 for registration,
legal, accounting and miscellaneous fees and expenses. The selling shareholders
will be solely responsible for commissions and discounts of brokers, dealers or
agents, other selling expenses and the fees and expenses of their own counsel,
if any, none of which will be borne by us.

         In offering the securities, the selling shareholders and any
broker-dealers and any other participating broker-dealers who execute sales for
the selling shareholders may be deemed to be "underwriters" within the meaning
of Section 2(11) of the Securities Act of 1933 in connection with such sales,
and any profits realized by the selling shareholders and the compensation of
such broker-dealers may be deemed to be underwriting discounts and commissions.
In addition, any shares covered by this prospectus which qualify for sale
pursuant to Rule 144 may be sold under Rule 144 rather than pursuant to this
prospectus. Also, if we are notified by a selling shareholder that a donee or
pledgee intends to sell more than 500 shares, a supplement to this prospectus
will be filed naming any donee or pledgee offering the shares before such a sale
is permissible under this prospectus.

         We have informed the selling shareholders that while they are selling
the securities, they (1) are required to comply with Regulation M under the
Securities Exchange Act of 1934 (as described in more detail below), (2) may not
engage in any stabilization activity, except as permitted under the Exchange
Act, (3) are required to furnish each broker-dealer (who may offer this common
stock) copies of this

                                       17





prospectus, and (4) may not bid for or purchase any securities of Wintrust or
attempt to induce any person to purchase any such securities except as permitted
under the Exchange Act.

         Regulation M under the Exchange Act prohibits, with certain exceptions,
participants in a distribution from bidding for or purchasing, for an account in
which the participant has a beneficial interest, any of the securities that are
the subject of the distribution. Regulation M also governs bids and purchases
made in order to stabilize the price of a security in connection with a
distribution of the security.

                                 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 have been passed upon for us by Vedder, Price, Kaufman & Kammholz,
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.

                                       18





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

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

         o        our Current Report on Form 8-K filed with the SEC on May 3,
                  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 (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 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

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