Exhibit 8.1

                       [Letterhead of Barack Ferrazzano]



                                                                 August 20, 2003


Advantage National Bancorp, Inc.
75 East Turner Avenue
Elk Grove Village, Illinois  60007


         Re:      Opinion Regarding Material Federal Income Tax Consequences
                  ----------------------------------------------------------

Ladies and Gentlemen:

         We have acted as special counsel to Advantage  National Bancorp,  Inc.,
an Illinois  corporation  ("Company"),  in connection  with the  negotiation and
execution  of an  Agreement  and Plan of  Merger,  dated as of July 2, 2003 (the
"Agreement"),   by  and  among  Wintrust  Financial  Corporation,   an  Illinois
corporation  ("Acquiror"),  Wintrust  Merger Co., an  Illinois  corporation  and
wholly-owned subsidiary of Acquiror ("Sub"), and Company, whereby Sub will merge
with and into Company  with  Company  surviving  (the  "Merger"),  as more fully
described in the Registration  Statement on Form S-4, filed by Acquiror with the
Securities and Exchange  Commission (the  "Commission")  on August __, 2003 (the
"Registration  Statement")  under the  Securities  Act of 1933,  as amended (the
"Act"). This opinion is being delivered to you pursuant to Section 8.7(b) of the
Agreement.

         In  connection  with this  opinion,  we have  reviewed  the  Agreement,
including  all  exhibits  thereto,  and such other  documents  and records as we
deemed  necessary  or  appropriate  (collectively,   the  "Documents").  In  our
examination  of  the  Documents,   we  have  assumed  their   completeness   and
authenticity, and we have further assumed that each of the Documents has been or
will be duly  authorized  and executed in the form as examined by us and will be
binding upon all parties thereto.  We are expressly relying for purposes of this
opinion on the facts,  information,  representations,  warranties  and covenants
contained  in  the  Documents.  In  addition,  we  are  expressly  relying  upon
additional  representations  of fact made by Company  in a letter  dated of even
date  hereof  and by  Acquiror  and Sub in a letter  dated of even date  hereof,
delivered to us in  connection  with this  opinion,  as well as facts learned in
discussions  with  certain  officers of Company and  certain  other  assumptions
stated  herein.  We are  relying  upon the  accuracy of any  representations  or
statements made that are qualified by the maker's knowledge or belief as if such
representations or statements were made without such qualification. We have also
assumed that as to all matters for which a person or entity has represented that
such person or entity is not a party to, does not have,  or is not aware of, any
plan, intention,  understanding, or agreement, there is no such plan, intention,
understanding, or agreement. We have not been asked to and have not attempted to
verify any  facts,  information,  warranties  or  representations  (collectively





Advantage National Bancorp, Inc.
August 20, 2003
Page 2

"statements")  through  independent  investigation and are assuming that each is
true,  correct  and  complete  as  of  the  date  hereof  and  that  no  actions
inconsistent with such statements have occurred or will occur.

         In connection  with this opinion,  we have assumed that the Merger will
qualify as a merger under all applicable  state business  corporation  statutes,
and that the Merger will be effected  and  consummated  in  accordance  with the
terms and conditions of the Agreement,  including  satisfaction  of all material
covenants and conditions to the obligations of the parties without  amendment or
waiver  thereof.  We have also  assumed  that none of the parties  will take any
action  after the  Merger  that  would  cause the  Merger  not to  qualify  as a
reorganization within the meaning of Section 368(a) of the Internal Revenue Code
of 1986, as amended (the "Code").

         Based on and subject to the foregoing,  including,  without limitation,
the  qualifications,   exceptions  and  assumptions  set  forth  above  and  the
exceptions,  qualifications  and  limitations set forth below, it is our opinion
that (i) the Merger  will  constitute  a  reorganization  within the  meaning of
Section  368(a) of the Code,  (ii) each of Company and Acquiror will be a "party
to a reorganization" within the meaning of Section 368(b) of the Code, and (iii)
the discussion contained in the proxy  statement/prospectus  included as part of
the  Registration  Statement under the heading  "DESCRIPTION OF THE MERGER - Tax
consequences of the merger"  constitutes,  in all material respects,  a fair and
accurate  summary of the United States  federal income tax  consequences  of the
Merger to the parties described therein.

         We express no opinion as to the tax  treatment  of the Merger under the
provisions  of any  other  sections  of the Code or under  any  state,  local or
foreign tax laws which also may be  applicable  thereto or as to any other party
in the  Merger,  nor do we express  any  opinion as to  non-tax  issues  such as
corporate law or securities law matters.  In addition,  we express no opinion as
to the tax  treatment  of any  conditions  existing  at the time of, or  effects
resulting from,  transactions  which are not specifically  addressed  herein. We
express  no  opinion as to whether  the above  discussion  addresses  all of the
United States federal or state income tax consequences of the Merger that may be
applicable to Acquiror, Sub, Company, or the Company stockholders.

         The  opinions  stated  herein  represent  our legal  judgment as to the
described  federal income tax  consequences of the Merger.  Our opinion is based
upon the existing  Code,  Income Tax  Regulations  promulgated  thereunder,  and
administrative and judicial  determinations,  all of which are subject to change
either prospectively or retroactively,  and our knowledge of the facts as of the
date hereof. If either (i) the relevant facts at the time of closing differ from
those represented or stated to us or reflected by the Documents, (ii) the Merger
is completed  under terms not contained in the Agreement,  (iii) our assumptions
prove  to  be  untrue,  or  (iv)  the  existing   authorities  are  modified  by
legislative,  administrative or judicial action,  our conclusions may differ and
this  opinion  may not be relied  upon.  In such  event,  we do not  assume  any
responsibility  to provide a revised  opinion or other advice,  and we assume no
duty to  communicate  with you with  respect  to any  matter  that  comes to our
attention hereafter.





Advantage National Bancorp, Inc.
August 20, 2003
Page 3


         You should be aware that no ruling has been sought or obtained from the
Internal   Revenue  Service  (the  "Service")  as  to  the  federal  income  tax
consequences  of any aspect of the Merger and that our opinion is not binding on
the Service.  You should also be aware that there can be no assurance,  and none
is hereby  given,  that the  Service  will not take a position  contrary  to the
position reflected in the foregoing opinion,  or that our opinion will be upheld
by the courts if challenged by the Service.

         We hereby  consent to the use of this  opinion in  connection  with the
Registration  Statement.  In giving  such  consent,  however,  we do not  hereby
concede  that we are within the  category of persons  whose  consent is required
under  Section  7 of the Act or the  rules  and  regulations  of the  Commission
promulgated thereunder.

         We are  furnishing  this  opinion  to you  solely  for your  benefit in
connection with the transactions contemplated by the Agreement. This opinion may
not be relied upon by any other party without our prior written consent, nor may
it be used,  circulated,  quoted or otherwise  referred to for any other purpose
without our prior written consent.

                                                    Very truly yours,



                                                /s/ BARACK FERRAZZANO KIRSCHBAUM
                                                      PERLMAN & NAGELBERG LLC