<?xml version="1.0" encoding="UTF-8"?><edgarSubmission xmlns="http://www.sec.gov/edgar/ownership" xmlns:com="http://www.sec.gov/edgar/common">
  <!-- Generated by Workiva -->
  <headerData>
    <submissionType>144</submissionType>
    <filerInfo>
      <filer>
        <filerCredentials>
          <cik>0001244290</cik>
          <ccc>XXXXXXXX</ccc>
        </filerCredentials>
      </filer>
      <liveTestFlag>LIVE</liveTestFlag>



    </filerInfo>
  </headerData>
  <formData>
    <issuerInfo>
      <issuerCik>0001015328</issuerCik>
      <issuerName>Wintrust Financial Corporation</issuerName>
      <secFileNumber>001-35077</secFileNumber>
      <issuerAddress>
        <com:street1>1719 Shore Acres Drive</com:street1>
        <com:city>Lake Forest</com:city>
        <com:stateOrCountry>IL</com:stateOrCountry>
        <com:zipCode>60044</com:zipCode>
      </issuerAddress>
      <issuerContactPhone>847-939-9000</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>Edward J. Wehmer</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>Chairman</relationshipToIssuer>
        <relationshipToIssuer>Director</relationshipToIssuer>
        <relationshipToIssuer>Executive Officer</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>Wintrust Investments, LLC</name>
        <address>
          <com:street1>231 S. LaSalle Street, 13th Floor</com:street1>
          <com:city>Chicago</com:city>
          <com:stateOrCountry>IL</com:stateOrCountry>
          <com:zipCode>60604</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>9500</noOfUnitsSold>
      <aggregateMarketValue>940500</aggregateMarketValue>
      <noOfUnitsOutstanding>108818</noOfUnitsOutstanding>
      <approxSaleDate>03/05/2024</approxSaleDate>
      <securitiesExchangeName>NASDAQ</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <acquiredDate>02/26/2024</acquiredDate>
      <natureOfAcquisitionTransaction>Purchase</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Wintrust Financial Corporation</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>9990</amountOfSecuritiesAcquired>
      <paymentDate>02/26/2024</paymentDate>
      <natureOfPayment>Cash</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>Y</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <noticeSignature>
      <noticeDate>03/06/2024</noticeDate>
      <signature>Edward J. Wehmer</signature>
    </noticeSignature>
  </formData>
</edgarSubmission>
