February, 2000

Dear Shareholders,

         This letter updates you on our financial performance through the fourth
quarter of 1999 and provides other news of Wintrust  Financial  Corporation.  We
are truly pleased with the progress  made in 1999 and think we have  significant
momentum to carry us forward into the coming years.

SUMMARY OF RESULTS

     o    Wintrust  generated  record earnings for the year (up 51%) and for the
          fourth quarter (up 35%);
     o    In 1999, our pre-tax operating  earnings  increased 201% over 1998 and
          were over 13 times higher than our pre-tax earnings in 1997;
     o    During  1999,  we grew our assets by 25% over a year ago and since the
          inception  of the first bank in  December  1991,  our annual  compound
          growth rate has been 54%.
     o    Accordingly, we continue to be one of the fastest growing de novo bank
          groups in the country, not only in assets, but in earnings as well;
     o    Our return on average  equity  increased 33% for the year and it stood
          at 12.66% for the fourth quarter;
     o    During 1999,  all of our community  banks reached  record asset levels
          and improved upon their profitability;
     o    First   Insurance   Funding  had  record  growth  in  premium  finance
          receivables volume;
     o    Wintrust  Asset  Management,  our  trust  and  investment  subsidiary,
          increased  its  assets  under  management  to $442  million  from $273
          million at the end of 1998;
     o    In October,  we acquired Tricom, Inc. which adds another earning asset
          niche,  bolsters  our fee revenue and is accretive to our earnings per
          share;
     o    Our asset  quality  remains  strong,  as the  level of  non-performing
          assets is very manageable and favorable compared to our peer group;
     o    We recently  announced the commencement of dividend  payments with our
          first ever semi-annual cash dividend of $0.05 per common share payable
          in February;
     o    We also  announced  the board's  approval of a stock  buyback  program
          authorizing  the  purchase  of up to 300,000  shares of the  Company's
          common stock.

         In summary,  it was a very good performance year for Wintrust Financial
Corporation.  While we feel that we have made excellent  progress on our journey
to improve profitability and

                                      - 1 -

franchise value, we feel in some respect like a mountain climber. That is, after
climbing  partially up the  "mountain"  we look down and realize how far we have
come in such a short  period  of time,  but we look up and see that  we've  only
begun our climb and have many more lofty goals to reach.


DIVIDEND DECLARATION

         We are  pleased  to  announce  that your  Board of  Directors  recently
approved the first  semi-annual  cash dividend in the amount of $0.05 per share.
The  dividend is payable on February  24, 2000 to  shareholders  of record as of
February 10, 2000. Given our increasing  profitability  levels and the fact that
some  investors  have  been  with  us for  eight  years,  we are  pleased  to be
commencing the payment of dividends.  As a growing  company,  we still intend to
retain the majority of our earnings to fund future  growth and continue to build
our franchise.

         The   commencement  of  a  dividend  payment  follows  through  on  our
commitment  that dividends  would be paid once we reached  consistent  levels of
profitability.  Annualized,  this dividend payment represents about 9% of 1999's
earnings. Most mature banking companies pay higher levels of dividends; however,
as a younger,  growth oriented  company,  our higher level of retained  earnings
will be utilized to support future growth.


STOCK BUYBACK AUTHORIZATION

         Additionally,  the Board approved a stock buyback  program  authorizing
the purchase of up to 300,000 shares of the Company's common stock, from time to
time, in open market or privately negotiated transactions. The shares authorized
to  be  repurchased  represent  approximately  3%  of  the  Company's  currently
outstanding shares. Shares repurchased,  if any, would be available for issuance
under the Company's stock incentive plan, employee stock purchase plan and other
corporate  purposes.  Such purchases,  at a time when our stock is statistically
cheap, would augment shareholder value.


FINANCIAL PROGRESS TO DATE

         Wintrust's  fourth quarter  earnings of 1999 increased to $2.8 million,
up from $2.1 million  during the same period in 1998,  an increase of 35%.  This
equates to $0.32 per diluted  common share for the three  months ended  December
31,  1999,  up from  $0.25 for the year ago  quarter.  The fourth  quarter  1999
earnings include a non-recurring  after-tax charge of approximately $100,000, or
$0.01 per common share, for a severance  payment related to the termination of a
former officer of one of our bank subsidiaries.

                                      - 2 -

         For the year ended December 31, 1999,  Wintrust generated net income of
$9.4 million compared to $6.2 million for the same period of 1998.  Earnings per
common share, on a fully diluted basis,  for the twelve months of 1999 increased
to $1.10 from $0.74 in 1998, a 49% increase.

         On the basis of pre-tax  operating  earnings,  our  performance is even
better. As you are aware,  prior to 1999 a large portion of our net income was a
result  of  recording  prior  net  operating  tax loss  benefits.  As such,  the
comparison of pre-tax earnings is more illuminating as it relates to progress in
our core  business.  Specifically,  pre-tax  operating  earnings  reached  $14.2
million for the twelve  months of 1999,  an increase of $9.4  million,  or 201%,
over the same  period a year ago and an  increase  of $13.1  million or 13 times
over the 1997 pre-tax earnings level.

         Our strategy of investing  heavily in the start-up of our de novo banks
continues  to pay off.  The  continuing  maturation  of our banks should lead to
accelerated  growth in our core earnings.  Also, our Tricom acquisition has been
immediately  accretive  to our  bottom  line  since its  addition  in the fourth
quarter of 1999.

         Growth in our major balance  sheet  categories  also  continues to look
good. As of December 31, 1999,  consolidated  assets increased to $1.68 billion,
or 25%, from $1.35 billion as of December 31, 1998. And since December 31, 1997,
our  consolidated  assets have grown $626 million,  or 59%. Our compound  growth
rate in assets over the past five years has averaged 37%.

         Loan demand  continues  to be strong.  Consolidated  net loans  reached
$1.28 billion as of December 31, 1999, an increase of $286 million,  or 29% over
the  prior  year.  This is a  result  of  steady  loan  origination  in our core
commercial  loan  portfolio,  strong  growth in our  insurance  premium  finance
business and the  receivables  generated by Tricom,  Inc. since the October 1999
acquisition. Also, as of year-end 1999, consolidated deposits increased to $1.46
billion from $1.23 billion a year ago, a 19% increase.

         In our third quarter update letter,  we stated that we had achieved our
objective of being an "asset  driven"  organization.  That is, the generation of
loans is outpacing  our growth in deposits.  This is  beneficial  to the Company
because it allows us to invest new  deposit  dollars in loans  which bear higher
interest rates than the alternative short-term  investments.  Being asset driven
also allows us to be more  competitive  in  designated  markets where we want to
increase  market share  because we are  generating  sufficient  higher  yielding
assets to invest the new  deposits.  Through  the fourth  quarter of 1999,  this
trend has continued. Because of our strong loan generation during the past three
quarters, we were able to provide the banks with additional liquidity by selling
approximately  $70  million  of  premium  finance  receivables  to an  unrelated
financial  institution  at a pre-tax gain of over $1.0  million.  We  anticipate
continuing this practice in the future as we balance growth and earnings.

                                      - 3 -

PERFORMANCE VERSUS GOALS

         Your Board of Directors and management set high standards for ourselves
and we want to be held accountable to you, the shareholders, for our performance
and the  attainment  of our goals.  Accordingly,  we  continue  to  publish  the
following goals for you to measure us by:

     o Core Net Interest Margin of 4 - 4 1/2 % o Net Overhead Ratio of 1 1/2 - 2
     % o Return on Assets of 1 1/2 % o Return on Equity of 20 - 25 %

         The following table tracks the performance of these goals and our asset
quality  position for each of the quarters in 1999 as well as the fourth quarter
of 1998. We have generally experienced improvement in these performance measures
and have actually surpassed some of our goals already.



                                                                    Quarter Ended
                                   ---------------------------------------------------------------------------------
                                     December 31,     September 30,      June 30,     March 31,      December 31,
                                         1999              1999            1999          1999            1998
                                         ----              ----            ----          ----            ----
                                                                                        
Core Net Interest Margin (1)            3.65%             3.59%           3.62%         3.66%           3.41%

Net Overhead Ratio                      1.89%             1.91%           2.04%         2.17%           2.24%

Return on Average Equity               12.66%            12.46%          11.55%         9.75%          11.09%

Return on Average Assets                0.68%             0.65%           0.62%         0.55%           0.63%

Non-Performing Assets
   as a percent of total assets         0.41%             0.38%           0.33%         0.37%           0.45%
 ------------------------
<FN>
(1) By definition,  our Core Net Interest Margin excludes certain  discretionary
investment  leveraging  transactions  and the net impact of the Company's  9.00%
Cumulative Trust Preferred Securities offering.
</FN>


         Our cost control and asset quality ratios  continue to improve.  During
the third  quarter of 1999,  we attained our goal of operating at a net overhead
ratio of less than 2%. And in the fourth quarter we made further  improvement on
that performance measure. As we continue to grow into our existing overhead,  we
are able to more  efficiently  leverage our  facilities  and staff.  We are also
pleased  with the low level of  problem  loans,  which  results  from  carefully
monitoring and diversifying our credit risks.

         In a period of rising rates,  growing the net interest margin continues
to be our biggest  challenge.  During the fourth quarter of 1999, the prime rate
increased  again (that  makes  three times in 1999) and yields on U.S.  Treasury
bills steadily increased  necessitating the need to raise certain deposit rates.
This put  increasing  pressure on our net  interest  margin as our  portfolio of
assets generally takes longer to re-price than our deposit base.  However,  over
time we believe that higher  interest  rates will be helpful to us in creating a
higher net  interest  margin.  Achieving  our goal is primarily  dependent  upon
controlling our funding costs and continuing to be a strong

                                      - 4 -

originator of a diversified  loan  portfolio.  The Company's new specialty asset
generation program (Community  Advantage(TM))  that provides lending and deposit
services to condominium,  homeowner and community  associations and our purchase
of Tricom,  Inc.  will assist in improving  our net interest  margin.  These new
sources of business will provide good growth for our  organization and diversify
our loan portfolio.

         As a result of this  progress,  for the year of 1999,  we have improved
our earnings and have  increased our return on equity to 11.6%,  up from 8.7% in
1998.  By balancing  our growth and  profitability,  we should  continue to make
progress towards attaining our financial goals.


OUR 4TH QUARTER "RUN RATE" PROJECTS CONTINUED EARNINGS GROWTH

         Our core earnings trend through the fourth quarter of 1999 continues to
improve.  If we were to annualize  the fourth  quarter's net income and earnings
per share, here's where we stand before any improvement in performance:

     o    Net income of $11.2 million
     o    Diluted earnings per share of $1.28

This  represents a 19% increase in net income and a 16% increase in earnings per
share over 1999 results,  before any improvement.  Most companies would be happy
with these increases in year-over-year  results but we have plans to continue to
grow the  earnings at a higher  rate.  If we were to factor in growth,  which is
reasonable  given  our  track  record,  the  continued  maturation  of our young
franchise and the positive impact that the Tricom  acquisition  will have on our
results,  we conclude that Wintrust  Financial  Corporation  should have another
impressive year in 2000.


GROWTH STRATEGIES

         You  have   seen   these   strategies   before,   but  they  are  worth
repeating--future growth will come from a variety of current and new strategies:

     o    Growing  our current  franchises  by adding new  customers  (increased
          market share) and new branches (new markets);

     o    Introducing new de novo banks in high opportunity markets that contain
          the right mix of demographic and  competitive  variables (high wealth,
          high big bank competition, low community bank competition);

     o    Acquiring  existing  community banks in high  opportunity  markets and
          acquiring  financial  services  firms to expand our portfolio of asset
          niches and fee revenues; and,

     o    Utilizing  the  internet  as a new  distribution  vehicle  for current
          products and a portal to marketing and distributing new products;

                                      - 5 -

         In 2000,  we have plans for new branch  openings for Lake Forest Bank &
Trust,  Hinsdale Bank & Trust,  Libertyville Bank & Trust, and Barrington Bank &
Trust.  Lake Forest Bank & Trust's newest branch in Highwood  serving  Highwood,
Fort Sheridan and Highland Park, should open during the first quarter of 2000 in
a temporary  facility while we begin  construction on a permanent  location.  We
also have an option to purchase a site for our seventh  separately  chartered de
novo bank. Not wanting to give the  competition  any  forewarning,  we will keep
that location a secret for the time being.

         Your  management  team and Board of  Directors  are  dedicated to being
disciplined with regard to pricing  potential  acquisitions so that they will be
accretive to earnings per share. We will not acquire financial institutions just
for the sake of growth through acquisition. Acquisition growth will need to fill
strategic goals as to franchise location,  additional  diversified earning asset
niches,  fee-based business niches to supplement  Wintrust's banking revenues or
other meaningful objectives.


INTERNET INITIATIVE

We are  pleased to  announce  that  considerable  progress  has been made on our
internet  initiative.  We  believe  that we will  offer  the most  sophisticated
internet  banking  service  of  any  community  bank.  We  also  have  a  unique
three-pronged   internet  strategy  that  is  feasible  given  our  asset-driven
operating philosophy:

     1.   Offer community  banking  financial  products and services to existing
          and new bank customers via each bank's internet web site.

     2.   Offer "private label" banking and financial  products via the internet
          to participating  affinity groups.  Our first such program is to offer
          First  Insurance  Funding  Corp.'s  network of  independent  insurance
          agents financial products for themselves and their customers.

     3.   Introduce a  free-standing  internet bank -  i-netbank.com  - to offer
          banking  products  outside of our market area. This should allow us to
          obtain  deposit  funding  at  targeted  rates  that will  assist us in
          managing  our  asset/liability  position,  as well as  offer  products
          through strategic alliances where we would receive fee income.

We have made good progress in the development of our internet financial services
web sites.  New web sites for our community  banks and First  Insurance  Funding
will be  completed  shortly  and  on-line  banking and bill pay are in the final
stages of testing.  A recent financial  services web site article indicates that
the three major  complaints  about current  banks' web sites are  "difficulty to
navigate",  "having  to  click  through  too  many  pages"  and  "confusing  and
distracting   materials".   We   believe   our   new   community   bank   sites'
state-of-the-art  navigation  system allows users to "get where they want to go"
quickly.  First  Insurance  Funding's  new web site  also  offers  products  and
services that are unmatched in the industry.

                                      - 6 -

         We are also dedicated to developing a top-notch operations and customer
service  group that will be  responsible  for  servicing our new bank web sites.
Since superior customer service is our mission, we believe providing unsurpassed
back office  customer  service  support is also  critical to making our internet
banking a success.

         This  internet  banking  technology  is the portal for future high tech
distribution initiatives by Wintrust's community banks, First Insurance Funding,
Wintrust  Asset  Management  and Tricom.  While most of our  customers  want the
benefits of our  old-fashioned  banking  service,  there is a growing  demand to
provide these same services via the  convenience of the internet.  Our banks and
other subsidiaries will be leaders in this area as well.


FIRST INSURANCE FUNDING CORP.

         First Insurance Funding Corp.  (FIRST) generated record volume in 1999.
With  approximately $690 million in volume for the twelve months ending December
31,  1999,  First  Insurance  Funding's  volume  grew  by 40%  over  1998.  This
unprecedented  growth comes as a result of continued  investments in technology,
improved  efficiency,  and  targeted  sales and  marketing.  In 2000,  we expect
continued  portfolio  growth to come from internal  growth and from our alliance
with Premium Finance  Holdings,  a sales  organization with which FIRST recently
entered into joint marketing agreement.

         FIRST's  new  internet  initiative  will bring its  customers a host of
services  currently  unavailable  in the  premium  finance  industry,  including
on-line  quoting,  account  information,   sales  and  marketing  materials  and
portfolio analysis.  The improved service and accessibility  offered by this new
web site will allow  FIRST's  customers  to more easily and  efficiently  quote,
process and record loans,  helping FIRST  maintain its low overhead  costs while
growing its  business.  And providing  financial  services to the agents and the
agent's customers is a value-added benefit that only FIRST can offer.


ASSET MANAGEMENT AND TRUST UPDATE

         Our trust and investment subsidiary, Wintrust Asset Management Company,
continues  to  increase  its  assets  under  management  and its  march  towards
profitability.  By the end of the fourth quarter,  assets under  management were
just over $440  million.  For the year,  we have  generated  approximately  $1.2
million in fee income and are now  generating  in excess of  $120,000 in monthly
fee income.  We have assembled a very qualified  staff of experienced  trust and
investment  professionals  at  Wintrust  Asset  Management  Company and they are
poised  to move  the  company  to a higher  level  of  growth  in  assets  under
management.  Income  generated  from our trust and  investment  activities is an
important  source of fee income that will help  Wintrust  diversify  its revenue
base.

                                      - 7 -

TRICOM, INC.

         Our  newest  member of the  Wintrust  family,  Tricom,  Inc.,  finances
temporary help companies and administers their payrolls. This has been a growing
business  throughout the economic cycle, and the potential for further growth is
outstanding.  The credit loss experience of Tricom's strong  management team has
been  excellent.  We are very pleased to welcome the Tricom team aboard and look
forward to their contributions to Wintrust's success.


STOCK PRICE PERFORMANCE

         The  following  graph  depicts  the  significant  annual  growth in net
income, net revenues and assets achieved by Wintrust Financial  Corporation over
the course of the past two years.  Couple these growth results with solid credit
quality,  improving cost efficiencies and the unique story of our young company,
and you would  expect  that our stock  price  would be ahead of its level of one
year ago. Unfortunately, it is not. As the graph also shows, our stock price has
performed  in line with the  composite  Nasdaq Bank Index over the course of the
last two years in spite of our well above average growth record.  Wintrust, like
other financial and small-cap stocks,  has been left behind in this market which
has favored high technology, internet, and ".com" companies.

         Companies  historically  are rewarded for consistent  growth in profits
and we think the market will  recognize our  performance  as we continue to post
positive trends. Our management,  bank directors and their families own over 25%
of our outstanding  stock,  so making Wintrust a rewarding  investment is a high
priority.

The graph included in this section portrays the percentage change of certain key
performance  data over a two year period from  December 31, 1997 to December 31,
1999, as follows:

Net Income - growth of 95 percent
Net  Revenues - growth of 81 percent
Assets - growth of 59 percent

WTFC  Stock  Price - decline  of 10 percent
Nasdaq  Bank Index - decline of 19 percent



                                      - 8 -


SUMMARY

         We  are  grateful  for  your  support  of  our   organization  and  are
enthusiastic  about making the year 2000 another good year in terms of growth in
earnings and assets.


                                  Yours truly,




                  John S. Lillard              Edward J. Wehmer
                  Chairman                     President and CEO







- --------------------------------------------------------------------------------
FORWARD-LOOKING STATEMENTS
- --------------------------------------------------------------------------------

This  letter  contains  forward-looking  statements  within  the  meaning of the
Private  Securities  Litigation Reform Act of 1995 with respect to the Company's
projected growth,  anticipated earnings,  earnings per share and other financial
measure  improvements,  and stock price  performance,  all of which are based on
estimates.  Actual results could differ  materially  from those addressed in the
forward-looking   statements   due  to  factors  such  as  changes  in  economic
conditions,  unanticipated changes in interest rates that negatively impact loan
growth,  net interest  income and the net interest  margin,  competition and the
related  pricing of loan and  deposit  products,  future  events  that may cause
unforeseen  loan  or  lease  losses,  slower  than  anticipated  growth  of  the
loan/receivables  portfolios  and the  deposit  base,  slower  than  anticipated
development and growth of Tricom's  business and of the new trust and investment
business,   unforeseen  difficulties  in  integrating  the  Tricom  acquisition,
unforeseen changes in the temporary staffing industry,  difficulties in adapting
successfully to  technological  changes as needed to compete  effectively in the
marketplace,  effectiveness  of the  Company's  and  its  vendors'  preparedness
efforts toward processing date sensitive data associated with the Year 2000, and
the  ability to attract and retain  experienced  senior  management.  Therefore,
there can be no assurances  that future actual results will  correspond to these
forward-looking statements.
- --------------------------------------------------------------------------------

                                      - 9 -