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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>As filed with the Securities and Exchange Commission
on May&nbsp;22, 2025</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right"><B>Registration No.&nbsp;333-</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNITED STATES</B></P>

<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SECURITIES AND EXCHANGE COMMISSION</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Washington, D.C. 20549</B></P>

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<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>FORM&nbsp;S-8</B></P>

<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>REGISTRATION STATEMENT</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B><I>UNDER</I></B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B><I>THE SECURITIES ACT OF 1933</I></B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><BR>
</FONT><FONT STYLE="font-size: 14pt"><B>WINTRUST FINANCIAL CORPORATION<BR>
</B></FONT>(Exact Name of Registrant as Specified in its Charter)</P>

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<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
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    <TD STYLE="width: 51%; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Illinois</B></FONT></TD>
    <TD STYLE="width: 49%; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>36-3873352</B></FONT></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(State or Other Jurisdiction of</FONT></TD>
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(I.R.S. Employer</FONT></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Incorporation or Organization)</FONT></TD>
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Identification Number)</FONT></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>9700 West Higgins Road, Suite&nbsp;800</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Rosemont,&nbsp;Illinois 60018</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Address, including zip code, of principal executive
offices)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Wintrust
Financial Corporation 2025 Stock Incentive Plan<BR>
</B></FONT>(Full title of the plan)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Kathleen M. Boege<BR>
Executive Vice President, Chief Legal Officer and Corporate Secretary<BR>
9700 West Higgins Road, Suite&nbsp;800<BR>
Rosemont,&nbsp;Illinois 60018<BR>
(847) 939-9000</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">(Name, address, and telephone number, including
area code, of agent for service)</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="border-top: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">Indicate by check mark whether the registrant is a large accelerated
filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of
 &ldquo;large accelerated filer,&rdquo; &ldquo;accelerated filer,&rdquo; &ldquo;smaller reporting company&rdquo; and &ldquo;emerging growth
company&rdquo; in Rule&nbsp;12b-2 of the Exchange Act.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 27%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Large accelerated filer</FONT></TD>
    <TD STYLE="width: 24%"><FONT STYLE="font-family: Wingdings; font-size: 10pt"><FONT STYLE="font-family: Wingdings">&#120;</FONT></FONT></TD>
    <TD STYLE="width: 25%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Accelerated filer</FONT></TD>
    <TD STYLE="width: 24%; text-align: center"><FONT STYLE="font-family: Wingdings; font-size: 10pt"><FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></TD></TR>
  <TR STYLE="vertical-align: top">
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Non-accelerated filer</FONT></TD>
    <TD><FONT STYLE="font-family: Wingdings; font-size: 10pt"><FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></TD>
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Smaller reporting company</FONT></TD>
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Wingdings; font-size: 10pt"><FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Emerging growth company</FONT></TD>
    <TD STYLE="vertical-align: top; text-align: center"><FONT STYLE="font-family: Wingdings; font-size: 10pt"><FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">If
an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying
with any new or revised financial accounting standards provided pursuant to Section&nbsp;7(a)(2)(B)&nbsp;of the Securities Act.&nbsp;</FONT><FONT STYLE="font-family: Wingdings"><FONT STYLE="font-family: Wingdings">&#168;</FONT></FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>PART&nbsp;I</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INFORMATION REQUIRED IN THE SECTION&nbsp;10(a)&nbsp;PROSPECTUS</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">All information required by Part&nbsp;I to be contained
in the prospectus is omitted from this Registration Statement in accordance with the explanatory note to Part&nbsp;I of Form&nbsp;S-8
and Rule&nbsp;428 under the Securities Act of 1933, as amended (the &ldquo;Securities Act&rdquo;). This Registration Statement on Form&nbsp;S-8
is filed by Wintrust Financial Corporation (the &ldquo;Registrant&rdquo;) regarding the Wintrust Financial Corporation 2025 Stock Incentive
Plan (the &ldquo;Plan&rdquo;). Documents containing the information required by Part&nbsp;I of the Registration Statement will be sent
or given to Plan participants as specified by Rule&nbsp;428(b)(1)&nbsp;under the Securities Act.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>PART&nbsp;II</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>INFORMATION REQUIRED IN THE REGISTRATION STATEMENT</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 3. Incorporation of Documents by Reference.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">The Registrant hereby incorporates
by reference in this Registration Statement the following documents and information previously filed with the Securities and Exchange
Commission (the &ldquo;Commission&rdquo;):</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="width: 1%"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000101532825000093/wtfc-20241231.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(a)&nbsp;</FONT></A></TD>
    <TD STYLE="width: 98%"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000101532825000093/wtfc-20241231.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">the Registrant&rsquo;s Annual Report on Form&nbsp;10-K for the year ended December&nbsp;31, 2024, filed with the Commission on February&nbsp;28, 2025</FONT>;</A></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="width: 1%"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000101532825000130/wtfc-20250331.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(b)</FONT></A></TD>
    <TD STYLE="width: 98%"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000101532825000130/wtfc-20250331.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">the Registrant&rsquo;s Quarterly Report on Form&nbsp;10-Q for the quarter ended March&nbsp;31, 2025, filed with the Commission on May&nbsp;5, 2025</FONT>;</A></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="width: 1%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(c)</FONT></TD>
    <TD STYLE="width: 98%; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">the
    Registrant&rsquo;s Current Reports on Form&nbsp;8-K, filed with the Commission&nbsp;on&nbsp;</FONT><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000110465925046807/tm2513736d5_8k.htm" STYLE="-sec-extract: exhibit">May&nbsp;9,
    2025</A>, <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000110465925048536/tm2515112d1_8k.htm" STYLE="-sec-extract: exhibit">May&nbsp;14,
    2025</A>, and <A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000110465925051990/tm2515739d3_8k.htm" STYLE="-sec-extract: exhibit">May 22, 2025</A>; and</TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
  <TR STYLE="vertical-align: top">
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="width: 2%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(d)</FONT></TD>
    <TD STYLE="width: 97%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">the description of the Registrant&rsquo;s common stock, no par value per share (the &ldquo;Common Stock&rdquo;), contained in the Registrant&rsquo;s Registration Statement on <A HREF="https://www.sec.gov/Archives/edgar/data/1015328/0000913849-97-000004-index.html" STYLE="-sec-extract: exhibit">Form&nbsp;8-A filed with the Commission on January&nbsp;3, 1997</A></FONT> under the Securities Exchange Act of 1934, as amended (the &ldquo;Exchange Act&rdquo;), including any amendments or reports filed for the purpose of updating such description, including <A HREF="https://www.sec.gov/Archives/edgar/data/1015328/000101532824000083/exhibit41registrantsecurit.htm" STYLE="-sec-extract: exhibit">Exhibit&nbsp;4.1 of the Registrant&rsquo;s Annual Report on Form&nbsp;10-K for the year ended December&nbsp;31, 2023, filed with the Commission on February&nbsp;28, 2024</A>.</TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">All documents subsequently filed by the Registrant
with the Commission pursuant to Sections 13(a), 13(c), 14, and 15(d)&nbsp;of the Exchange Act prior to the filing of a post-effective
amendment to this Registration Statement, which indicates that all securities offered hereby have been sold or which deregisters all securities
then remaining unsold, shall be deemed to be incorporated by reference into this Registration Statement and to be a part hereof from the
respective dates of filing of such documents (such documents, and the documents enumerated above, being hereinafter referred to as &ldquo;Incorporated
Documents&rdquo;).</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Any statement contained herein or in an Incorporated
Document shall be deemed to be modified or superseded for purposes of this Registration Statement or the related prospectus to the extent
that a statement contained herein or in any subsequently filed Incorporated Document modifies or supersedes such statement. Any such statement
so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Notwithstanding the foregoing, unless specifically
stated to the contrary, none of the information disclosed by the Registrant under Items 2.02 or 7.01 of any Current Report on Form&nbsp;8-K,
including the related exhibits under Item 9.01, that the Registrant may from time to time furnish to the Commission will be incorporated
by reference into, or otherwise included in, this Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 4. Description of Securities.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Not applicable.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 5. Interests of Named Experts and Counsel.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">The legality of the securities being registered
hereby has been passed on by Kathleen M, Boege, the Registrant&rsquo;s Executive Vice President, Chief Legal Officer, and Corporate Secretary.
Ms.&nbsp;Boege is eligible to participate in the Plan and beneficially owns or has rights to acquire an aggregate of less than 1.0% of
the Common Stock.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify"><B>Item 6. Indemnification of Directors and Officers.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Section&nbsp;8.75 of the Illinois Business Corporation
Act (the &ldquo;IBCA&rdquo;) provides generally and in pertinent parts that an Illinois corporation may indemnify its directors, officers,
employees and agents, or anyone serving at the request of the corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses (in the case of actions by or in the right of the corporation)
or against expenses, judgments, fines, and settlements (in all other cases) actually and reasonably incurred by them in connection with
any action, suit, or proceeding if, in connection with the matters in issue, they acted in good faith and in a manner they reasonably
believed to be in, or not opposed to, the best interests of the corporation and, in connection with any criminal suit or proceeding, if
in connection with the matters in issue, they had no reasonable cause to believe their conduct was unlawful, provided that no indemnification
shall be made with respect to any claim, issue, or matter as to which such person has been adjudged to have been liable to the corporation,
unless and only to the extent that the court in which such action or suit was brought shall determine upon application that, despite the
adjudication of liability, such person is fairly and reasonably entitled to indemnity. If a present or former director, officer or employee
of an Illinois corporation has been successful in the defense of any such action, suit or proceeding, claim, issue or matter, such person
shall be indemnified by the corporation against expenses if, in connection with the matters in issue, they acted in good faith and in
a manner they reasonably believed to be in, or not opposed to, the best interests of the corporation.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Section&nbsp;8.75 of the IBCA further permits an
Illinois corporation to pay expenses incurred by an officer or director in defending a civil or criminal action, suit or proceeding in
advance of the final disposition of such action, suit or proceeding if the director or officer undertakes to repay such amount if it is
ultimately determined that such person is not entitled to be indemnified by the corporation. An Illinois corporation may also grant additional
indemnification through its by-laws, agreements, votes of shareholders or disinterested directors, or otherwise, and may purchase and
maintain insurance on behalf of any indemnifiable person against any liability asserted against such person and incurred by such person
in his or her capacity as an indemnifiable person whether or not the corporation would have the power to indemnify such person against
liability under the terms of Section&nbsp;8.75 of the IBCA.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Article&nbsp;NINE of the Registrant&rsquo;s Amended
and Restated Articles of Incorporation, as amended, and Article&nbsp;VI of the Registrant&rsquo;s Amended and Restated By-Laws, as amended,
provide that the Registrant shall, to the full extent permitted by law, indemnify those persons whom the Registrant may indemnify pursuant
thereto, and contain provisions substantially similar to Section&nbsp;8.75 of the IBCA.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">The Registrant has entered into individual indemnification
agreements with each of its non-employee directors and certain of its executive officers, which implement with more specificity the indemnification
provisions provided by the Registrant&rsquo;s Amended and Restated By-Laws and provide, among other things, that to the fullest extent
permitted by applicable law, the Registrant will indemnify such director or officer against any and all losses, expenses and liabilities
arising out of such director&rsquo;s or officer&rsquo;s service as a director or officer of the Registrant, as the case may be. The indemnification
agreements also contain detailed provisions concerning expense advancement and reimbursement. The indemnification agreements are in addition
to any other rights each non-employee director or officer may be entitled to under the Registrant&rsquo;s Amended and Restated Articles
of Incorporation, Amended and Restated By-Laws and applicable law.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">The Registrant maintains insurance policies under
which its directors and officers are insured, within the limits and subject to the limitations of the policies, against certain expenses
in connection with the defense of actions, suits or proceedings, and certain liabilities which might be imposed as a result of such actions,
suits or proceedings, to which they are parties by reason of being or having been such directors or officers.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 7. Exemption from Registration Claimed.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Not applicable.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><B>Item 8. Exhibits.</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR>
    <TD STYLE="vertical-align: top; width: 14%; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Exhibit&nbsp;No.</FONT></TD>
    <TD STYLE="width: 2%">&nbsp;</TD>
    <TD STYLE="vertical-align: top; width: 84%; text-align: justify"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Description</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify">&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000110465925031671/tm252508-1_def14a.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">4.1</FONT></A></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="https://www.sec.gov/ix?doc=/Archives/edgar/data/1015328/000110465925031671/tm252508-1_def14a.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Wintrust Financial Corporation 2025 Stock Incentive Plan, incorporated herein by reference to Annex A to the Registrant&rsquo;s Definitive Proxy Statement, filed with the Commission on April&nbsp;3,&nbsp; 2025.</FONT></A></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex5-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">5.1*</FONT></A></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex5-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Opinion of Kathleen M. Boege,&nbsp;Esq., with respect to validity of issuance of securities.</FONT></A></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex5-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">23.1*</FONT></A></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex5-1.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent of Kathleen M. Boege,&nbsp;Esq. (included in Exhibit&nbsp;5.1).</FONT></A></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex23-2.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">23.2*</FONT></A></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="tm2515739d1_ex23-2.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Consent of Independent Registered Public Accounting Firm.</FONT></A></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="#a_001"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">24.1*</FONT></A></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: justify"><A HREF="#a_001"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Power of Attorney (contained in signature page&nbsp;to this Registration Statement).</FONT></A></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; padding-bottom: 1pt; text-align: justify"><A HREF="tm2515739d1_ex-filingfees.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">107*</FONT></A></TD>
    <TD STYLE="padding-bottom: 1pt">&nbsp;</TD>
    <TD STYLE="vertical-align: top; padding-bottom: 1pt; text-align: justify"><A HREF="tm2515739d1_ex-filingfees.htm" STYLE="-sec-extract: exhibit"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Filing Fee Table.</FONT></A></TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">* Filed herewith.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Item 9.</B></FONT> <FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Undertakings.</B></FONT></P>


<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">(a)&nbsp;The Registrant hereby undertakes:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 0.5in">(1)&nbsp;To file, during any period in which offers or sales
are being made, a post-effective amendment to this Registration Statement:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 1in">(i)&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;To
include any prospectus required by Section&nbsp;10(a)(3)&nbsp;of the Securities Act;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 1in">(ii)&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;To
reflect in the prospectus any facts or events arising after the effective date of the Registration Statement (or the most recent post-effective
amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the Registration
Statement; and</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 1in">(iii)&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;To
include any material information with respect to the plan of distribution not previously disclosed in the Registration Statement or any
material change to such information in the Registration Statement;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><I>provided,
however,</I></FONT>&nbsp;that paragraphs (a)(1)(i)&nbsp;and (a)(1)(ii)&nbsp;do not apply if the information required to be included in
a post-effective amendment by those paragraphs is contained in reports filed with or furnished to the Commission by the Registrant pursuant
to Section&nbsp;13 or Section&nbsp;15(d)&nbsp;of the Exchange Act that are incorporated by reference in the Registration Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 0.5in">(2)&nbsp;That, for the purpose of determining any liability
under the Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities
offered therein, and the offering of such securities at that time shall be deemed to be the initial&nbsp;<I>bona fide</I>&nbsp;offering
thereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 0.5in">(3)&nbsp;To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the termination of the offering.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">(b)&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;The
Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act, each filing of the Registrant&rsquo;s
annual report pursuant to Section&nbsp;13(a)&nbsp;or Section&nbsp;15(d)&nbsp;of the Exchange Act (and, where applicable, each filing of
an employee benefit plan&rsquo;s annual report pursuant to Section&nbsp;15(d)&nbsp;of the Exchange Act) that is incorporated by reference
in the Registration Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering
of such securities at that time shall be deemed to be the initial&nbsp;<I>bona fide</I>&nbsp;offering thereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">(c)&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;&#8239;Insofar
as indemnification for liabilities arising under the Securities Act may be permitted to directors, officers and controlling persons of
the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Commission
such indemnification is against public policy as expressed in the Securities Act and is, therefore, unenforceable. In the event that a
claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director,
officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director,
officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel
the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification
by it is against public policy as expressed in the Securities Act and will be governed by the final adjudication of such issue.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"></P>

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    <DIV STYLE="break-before: page; margin-top: 6pt; margin-bottom: 12pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
    <!-- Field: /Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SIGNATURES</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Pursuant to the requirements of the Securities
Act of 1933, as amended, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for
filing on Form&nbsp;S-8 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the Village of Rosemont, State of Illinois, on May&nbsp;22, 2025.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD COLSPAN="2"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>WINTRUST FINANCIAL CORPORATION</B></FONT></TD></TR>
  <TR>
    <TD STYLE="width: 50%">&nbsp;</TD>
    <TD STYLE="width: 3%">&nbsp;</TD>
    <TD STYLE="width: 47%">&nbsp;</TD></TR>
  <TR STYLE="vertical-align: top">
    <TD>&nbsp;</TD>
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">By:</FONT></TD>
    <TD STYLE="border-bottom: Black 1pt solid"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Kathleen M. Boege</FONT></TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Kathleen
M. Boege</FONT></TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top">Executive Vice President, Chief Legal Officer, and Corporate Secretary</TD></TR>
  </TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><A NAME="a_001"></A><B>POWER OF ATTORNEY</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Each person whose signature appears below constitutes
and appoints each of Timothy S. Crane, David A. Dykstra and Kathleen M. Boege, as his or her true and lawful attorney-in-fact with full
power of substitution and resubstitution, in any and all capacities, to sign this registration statement or amendments thereto and to
file the same, with all exhibits thereto and other documents in connection therewith, with the Commission, granting unto each of said
attorneys-in-fact and agents full power and authority to do and perform each and every act and thing requisite and necessary to be done
in and about the premises, as fully to all intents and purposes as he might or could do in person, hereby ratifying and conforming all
that said attorneys-in-fact and agents, or their substitutes, may lawfully do or cause to be done by virtue hereof.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-indent: 0.5in">Pursuant to the requirements of the Securities
Act, this Registration Statement has been signed by the following persons in the capacities indicated on May&nbsp;22, 2025.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR>
    <TD STYLE="vertical-align: top; width: 35%; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Name</B></FONT></TD>
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="vertical-align: top; width: 64%; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Title</B></FONT></TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ H. Patrick Hackett,&nbsp;Jr.</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Chairman of the Board of Directors</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">H. Patrick Hackett,&nbsp;Jr.</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Timothy S. Crane</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">President, Chief Executive Officer and Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Timothy S. Crane</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(Principal Executive Officer)</FONT></TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ David L. Stoehr</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Executive Vice President and Chief Financial Officer</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">David L. Stoehr</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(Principal Financial Officer)</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top">&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Jeffrey D. Hahnfeld</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Executive Vice President, Controller, and Chief Accounting Officer </FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Jeffrey D. Hahnfeld</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">(Principal Accounting Officer)</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top">&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-bottom: black 1pt solid"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Elizabeth H. Connelly</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Elizabeth H. Connelly</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Peter D. Crist</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Peter D. Crist</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ William J. Doyle</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">William J. Doyle</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Marla F. Glabe</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Marla F. Glabe</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
</TABLE>

<P STYLE="margin: 0"></P>

<!-- Field: Page; Sequence: 6 -->
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    <DIV STYLE="break-before: page; margin-top: 6pt; margin-bottom: 12pt"><P STYLE="margin: 0pt">&nbsp;</P></DIV>
    <!-- Field: /Page -->

<P STYLE="margin: 0">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%; border-collapse: collapse">
  <TR>
    <TD STYLE="vertical-align: top; width: 35%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"></FONT></TD>
    <TD STYLE="width: 1%">&nbsp;</TD>
    <TD STYLE="vertical-align: top; width: 64%"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Deborah L. Hall Lefevre</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; text-align: center">&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Brian A. Kenney</FONT></TD>
    <TD>&nbsp;</TD>
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Brian A. Kenney</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Suzet M. McKinney</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Suzet M. McKinney</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Richard L. Postma</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Richard L. Postma</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="border-bottom: Black 1pt solid"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Gregory A. Smith</FONT></TD>
    <TD>&nbsp;</TD>
    <TD><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Gregory A. Smith</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Karin Gustafson Teglia</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Karin Gustafson Teglia</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  <TR>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">/s/ Alex E. Washington,&nbsp;III</FONT></TD>
    <TD>&nbsp;</TD>
    <TD STYLE="vertical-align: top"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Director</FONT></TD></TR>
  <TR>
    <TD STYLE="vertical-align: top; border-top: black 1pt solid; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">Alex E. Washington,&nbsp;III</FONT></TD>
    <TD>&nbsp;</TD>
    <TD>&nbsp;</TD></TR>
  </TABLE>
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[{"type": "S-8", "sequence": "1", "filename": "tm2515739d1_s8.htm", "description": "FORM S-8", "secsgml_size_bytes": 52086}]
{"company-data": {"conformed-name": "WINTRUST FINANCIAL CORP", "cik": "0001015328", "assigned-sic": "6022", "organization-name": "02 Finance", "ein": "363873352", "state-of-incorporation": "IL", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-287524", "film-number": "25977935"}, "business-address": {"street1": "9700 WEST HIGGINS ROAD, 8TH FLOOR", "city": "ROSEMONT", "state": "IL", "zip": "60018", "phone": "8479399000"}, "mail-address": {"street1": "9700 WEST HIGGINS ROAD, 8TH FLOOR", "city": "ROSEMONT", "state": "IL", "zip": "60018"}}
As filed with the Securities and Exchange Commission
on May 22, 2025
Registration No. 333-
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM S-8
REGISTRATION STATEMENT
UNDER
THE SECURITIES ACT OF 1933
WINTRUST FINANCIAL CORPORATION
(Exact Name of Registrant as Specified in its Charter)
Illinois
36-3873352
(State or Other Jurisdiction of
(I.R.S. Employer
Incorporation or Organization)
Identification Number)
9700 West Higgins Road, Suite 800
Rosemont, Illinois 60018
(Address, including zip code, of principal executive
offices)
Wintrust
Financial Corporation 2025 Stock Incentive Plan
(Full title of the plan)
Kathleen M. Boege
Executive Vice President, Chief Legal Officer and Corporate Secretary
9700 West Higgins Road, Suite 800
Rosemont, Illinois 60018
(847) 939-9000
(Name, address, and telephone number, including
area code, of agent for service)
Indicate by check mark whether the registrant is a large accelerated
filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of
 "large accelerated filer," "accelerated filer," "smaller reporting company" and "emerging growth
company" in Rule 12b-2 of the Exchange Act.
Large accelerated filer
x
Accelerated filer
¨
Non-accelerated filer
¨
Smaller reporting company
¨
Emerging growth company
¨
If
an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying
with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act.
¨
PART I
INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS
All information required by Part I to be contained
in the prospectus is omitted from this Registration Statement in accordance with the explanatory note to Part I of Form S-8
and Rule 428 under the Securities Act of 1933, as amended (the "Securities Act"). This Registration Statement on Form S-8
is filed by Wintrust Financial Corporation (the "Registrant") regarding the Wintrust Financial Corporation 2025 Stock Incentive
Plan (the "Plan"). Documents containing the information required by Part I of the Registration Statement will be sent
or given to Plan participants as specified by Rule 428(b)(1) under the Securities Act.
PART II
INFORMATION REQUIRED IN THE REGISTRATION STATEMENT
Item 3. Incorporation of Documents by Reference.
The Registrant hereby incorporates
by reference in this Registration Statement the following documents and information previously filed with the Securities and Exchange
Commission (the "Commission"):
(a)
the Registrant's Annual Report on Form 10-K for the year ended December 31, 2024, filed with the Commission on February 28, 2025
;
(b)
the Registrant's Quarterly Report on Form 10-Q for the quarter ended March 31, 2025, filed with the Commission on May 5, 2025
;
(c)
the
    Registrant's Current Reports on Form 8-K, filed with the Commission on
May 9,
    2025
,
May 14,
    2025
, and
May 22, 2025
; and
(d)
the description of the Registrant's common stock, no par value per share (the "Common Stock"), contained in the Registrant's Registration Statement on
Form 8-A filed with the Commission on January 3, 1997
under the Securities Exchange Act of 1934, as amended (the "Exchange Act"), including any amendments or reports filed for the purpose of updating such description, including
Exhibit 4.1 of the Registrant's Annual Report on Form 10-K for the year ended December 31, 2023, filed with the Commission on February 28, 2024
.
All documents subsequently filed by the Registrant
with the Commission pursuant to Sections 13(a), 13(c), 14, and 15(d) of the Exchange Act prior to the filing of a post-effective
amendment to this Registration Statement, which indicates that all securities offered hereby have been sold or which deregisters all securities
then remaining unsold, shall be deemed to be incorporated by reference into this Registration Statement and to be a part hereof from the
respective dates of filing of such documents (such documents, and the documents enumerated above, being hereinafter referred to as "Incorporated
Documents").
Any statement contained herein or in an Incorporated
Document shall be deemed to be modified or superseded for purposes of this Registration Statement or the related prospectus to the extent
that a statement contained herein or in any subsequently filed Incorporated Document modifies or supersedes such statement. Any such statement
so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.
Notwithstanding the foregoing, unless specifically
stated to the contrary, none of the information disclosed by the Registrant under Items 2.02 or 7.01 of any Current Report on Form 8-K,
including the related exhibits under Item 9.01, that the Registrant may from time to time furnish to the Commission will be incorporated
by reference into, or otherwise included in, this Registration Statement.
Item 4. Description of Securities.
Not applicable.
Item 5. Interests of Named Experts and Counsel.
The legality of the securities being registered
hereby has been passed on by Kathleen M, Boege, the Registrant's Executive Vice President, Chief Legal Officer, and Corporate Secretary.
Ms. Boege is eligible to participate in the Plan and beneficially owns or has rights to acquire an aggregate of less than 1.0% of
the Common Stock.
Item 6. Indemnification of Directors and Officers.
Section 8.75 of the Illinois Business Corporation
Act (the "IBCA") provides generally and in pertinent parts that an Illinois corporation may indemnify its directors, officers,
employees and agents, or anyone serving at the request of the corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses (in the case of actions by or in the right of the corporation)
or against expenses, judgments, fines, and settlements (in all other cases) actually and reasonably incurred by them in connection with
any action, suit, or proceeding if, in connection with the matters in issue, they acted in good faith and in a manner they reasonably
believed to be in, or not opposed to, the best interests of the corporation and, in connection with any criminal suit or proceeding, if
in connection with the matters in issue, they had no reasonable cause to believe their conduct was unlawful, provided that no indemnification
shall be made with respect to any claim, issue, or matter as to which such person has been adjudged to have been liable to the corporation,
unless and only to the extent that the court in which such action or suit was brought shall determine upon application that, despite the
adjudication of liability, such person is fairly and reasonably entitled to indemnity. If a present or former director, officer or employee
of an Illinois corporation has been successful in the defense of any such action, suit or proceeding, claim, issue or matter, such person
shall be indemnified by the corporation against expenses if, in connection with the matters in issue, they acted in good faith and in
a manner they reasonably believed to be in, or not opposed to, the best interests of the corporation.
Section 8.75 of the IBCA further permits an
Illinois corporation to pay expenses incurred by an officer or director in defending a civil or criminal action, suit or proceeding in
advance of the final disposition of such action, suit or proceeding if the director or officer undertakes to repay such amount if it is
ultimately determined that such person is not entitled to be indemnified by the corporation. An Illinois corporation may also grant additional
indemnification through its by-laws, agreements, votes of shareholders or disinterested directors, or otherwise, and may purchase and
maintain insurance on behalf of any indemnifiable person against any liability asserted against such person and incurred by such person
in his or her capacity as an indemnifiable person whether or not the corporation would have the power to indemnify such person against
liability under the terms of Section 8.75 of the IBCA.
Article NINE of the Registrant's Amended
and Restated Articles of Incorporation, as amended, and Article VI of the Registrant's Amended and Restated By-Laws, as amended,
provide that the Registrant shall, to the full extent permitted by law, indemnify those persons whom the Registrant may indemnify pursuant
thereto, and contain provisions substantially similar to Section 8.75 of the IBCA.
The Registrant has entered into individual indemnification
agreements with each of its non-employee directors and certain of its executive officers, which implement with more specificity the indemnification
provisions provided by the Registrant's Amended and Restated By-Laws and provide, among other things, that to the fullest extent
permitted by applicable law, the Registrant will indemnify such director or officer against any and all losses, expenses and liabilities
arising out of such director's or officer's service as a director or officer of the Registrant, as the case may be. The indemnification
agreements also contain detailed provisions concerning expense advancement and reimbursement. The indemnification agreements are in addition
to any other rights each non-employee director or officer may be entitled to under the Registrant's Amended and Restated Articles
of Incorporation, Amended and Restated By-Laws and applicable law.
The Registrant maintains insurance policies under
which its directors and officers are insured, within the limits and subject to the limitations of the policies, against certain expenses
in connection with the defense of actions, suits or proceedings, and certain liabilities which might be imposed as a result of such actions,
suits or proceedings, to which they are parties by reason of being or having been such directors or officers.
Item 7. Exemption from Registration Claimed.
Not applicable.
Item 8. Exhibits.
Exhibit No.
Description
4.1
Wintrust Financial Corporation 2025 Stock Incentive Plan, incorporated herein by reference to Annex A to the Registrant's Definitive Proxy Statement, filed with the Commission on April 3,  2025.
5.1*
Opinion of Kathleen M. Boege, Esq., with respect to validity of issuance of securities.
23.1*
Consent of Kathleen M. Boege, Esq. (included in Exhibit 5.1).
23.2*
Consent of Independent Registered Public Accounting Firm.
24.1*
Power of Attorney (contained in signature page to this Registration Statement).
107*
Filing Fee Table.
* Filed herewith.
Item 9.
Undertakings.
(a) The Registrant hereby undertakes:
(1) To file, during any period in which offers or sales
are being made, a post-effective amendment to this Registration Statement:
(i)             To
include any prospectus required by Section 10(a)(3) of the Securities Act;
(ii)            To
reflect in the prospectus any facts or events arising after the effective date of the Registration Statement (or the most recent post-effective
amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the Registration
Statement; and
(iii)           To
include any material information with respect to the plan of distribution not previously disclosed in the Registration Statement or any
material change to such information in the Registration Statement;
provided,
however,
that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if the information required to be included in
a post-effective amendment by those paragraphs is contained in reports filed with or furnished to the Commission by the Registrant pursuant
to Section 13 or Section 15(d) of the Exchange Act that are incorporated by reference in the Registration Statement.
(2) That, for the purpose of determining any liability
under the Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities
offered therein, and the offering of such securities at that time shall be deemed to be the initial
bona fide
offering
thereof.
(3) To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the termination of the offering.
(b)             The
Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act, each filing of the Registrant's
annual report pursuant to Section 13(a) or Section 15(d) of the Exchange Act (and, where applicable, each filing of
an employee benefit plan's annual report pursuant to Section 15(d) of the Exchange Act) that is incorporated by reference
in the Registration Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering
of such securities at that time shall be deemed to be the initial
bona fide
offering thereof.
(c)            Insofar
as indemnification for liabilities arising under the Securities Act may be permitted to directors, officers and controlling persons of
the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Commission
such indemnification is against public policy as expressed in the Securities Act and is, therefore, unenforceable. In the event that a
claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director,
officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director,
officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel
the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification
by it is against public policy as expressed in the Securities Act and will be governed by the final adjudication of such issue.
SIGNATURES
Pursuant to the requirements of the Securities
Act of 1933, as amended, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for
filing on Form S-8 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the Village of Rosemont, State of Illinois, on May 22, 2025.
WINTRUST FINANCIAL CORPORATION
By:
/s/ Kathleen M. Boege
Kathleen
M. Boege
Executive Vice President, Chief Legal Officer, and Corporate Secretary
POWER OF ATTORNEY
Each person whose signature appears below constitutes
and appoints each of Timothy S. Crane, David A. Dykstra and Kathleen M. Boege, as his or her true and lawful attorney-in-fact with full
power of substitution and resubstitution, in any and all capacities, to sign this registration statement or amendments thereto and to
file the same, with all exhibits thereto and other documents in connection therewith, with the Commission, granting unto each of said
attorneys-in-fact and agents full power and authority to do and perform each and every act and thing requisite and necessary to be done
in and about the premises, as fully to all intents and purposes as he might or could do in person, hereby ratifying and conforming all
that said attorneys-in-fact and agents, or their substitutes, may lawfully do or cause to be done by virtue hereof.
Pursuant to the requirements of the Securities
Act, this Registration Statement has been signed by the following persons in the capacities indicated on May 22, 2025.
Name
Title
/s/ H. Patrick Hackett, Jr.
Chairman of the Board of Directors
H. Patrick Hackett, Jr.
/s/ Timothy S. Crane
President, Chief Executive Officer and Director
Timothy S. Crane
(Principal Executive Officer)
/s/ David L. Stoehr
Executive Vice President and Chief Financial Officer
David L. Stoehr
(Principal Financial Officer)
/s/ Jeffrey D. Hahnfeld
Executive Vice President, Controller, and Chief Accounting Officer
Jeffrey D. Hahnfeld
(Principal Accounting Officer)
/s/ Elizabeth H. Connelly
Director
Elizabeth H. Connelly
/s/ Peter D. Crist
Director
Peter D. Crist
/s/ William J. Doyle
Director
William J. Doyle
/s/ Marla F. Glabe
Director
Marla F. Glabe
Director
Deborah L. Hall Lefevre
/s/ Brian A. Kenney
Director
Brian A. Kenney
/s/ Suzet M. McKinney
Director
Suzet M. McKinney
/s/ Richard L. Postma
Director
Richard L. Postma
/s/ Gregory A. Smith
Director
Gregory A. Smith
/s/ Karin Gustafson Teglia
Director
Karin Gustafson Teglia
/s/ Alex E. Washington, III
Director
Alex E. Washington, III