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  <!-- Generated by Workiva -->
  <headerData>
    <submissionType>144</submissionType>
    <filerInfo>
      <filer>
        <filerCredentials>
          <cik>0001349132</cik>
          <ccc>XXXXXXXX</ccc>
        </filerCredentials>
      </filer>
      <liveTestFlag>LIVE</liveTestFlag>



    </filerInfo>
  </headerData>
  <formData>
    <issuerInfo>
      <issuerCik>0001133311</issuerCik>
      <issuerName>Travelzoo</issuerName>
      <secFileNumber>000-50171</secFileNumber>
      <issuerAddress>
        <com:street1>590 Madison Avenue</com:street1>
        <com:street2>35th Floor</com:street2>
        <com:city>New York</com:city>
        <com:stateOrCountry>NY</com:stateOrCountry>
        <com:zipCode>10022</com:zipCode>
      </issuerAddress>
      <issuerContactPhone>2124844900</issuerContactPhone>
      <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>Azzurro Capital Inc.</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
      <relationshipsToIssuer>
        <relationshipToIssuer>10% Stockholder</relationshipToIssuer>
      </relationshipsToIssuer>
    </issuerInfo>
    <securitiesInformation>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <brokerOrMarketmakerDetails>
        <name>E*Trade Securities LLC</name>
        <address>
          <com:street1>200 Hudson Street</com:street1>
          <com:street2>Harborside 2, Suite 501</com:street2>
          <com:city>Jersey City</com:city>
          <com:stateOrCountry>NJ</com:stateOrCountry>
          <com:zipCode>07311</com:zipCode>
        </address>
      </brokerOrMarketmakerDetails>
      <noOfUnitsSold>50000</noOfUnitsSold>
      <aggregateMarketValue>626000</aggregateMarketValue>
      <noOfUnitsOutstanding>11095078</noOfUnitsOutstanding>
      <approxSaleDate>06/20/2025</approxSaleDate>
      <securitiesExchangeName>NASDAQ</securitiesExchangeName>
    </securitiesInformation>
    <securitiesToBeSold>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <acquiredDate>01/22/2001</acquiredDate>
      <natureOfAcquisitionTransaction>Contribution of all outstanding shares of Silicon Channels Corporation in exchange for shares in Travelzoo</natureOfAcquisitionTransaction>
      <nameOfPersonfromWhomAcquired>Travelzoo</nameOfPersonfromWhomAcquired>
      <isGiftTransaction>N</isGiftTransaction>
      <amountOfSecuritiesAcquired>50000</amountOfSecuritiesAcquired>
      <paymentDate>01/22/2001</paymentDate>
      <natureOfPayment>Exchange</natureOfPayment>
    </securitiesToBeSold>
    <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/16/2025</saleDate>
      <amountOfSecuritiesSold>10000</amountOfSecuritiesSold>
      <grossProceeds>126600</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/11/2025</saleDate>
      <amountOfSecuritiesSold>25000</amountOfSecuritiesSold>
      <grossProceeds>346000</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
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          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>06/02/2025</saleDate>
      <amountOfSecuritiesSold>5000</amountOfSecuritiesSold>
      <grossProceeds>63650</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/30/2025</saleDate>
      <amountOfSecuritiesSold>22500</amountOfSecuritiesSold>
      <grossProceeds>310725</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/29/2025</saleDate>
      <amountOfSecuritiesSold>18500</amountOfSecuritiesSold>
      <grossProceeds>248085</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/28/2025</saleDate>
      <amountOfSecuritiesSold>2000</amountOfSecuritiesSold>
      <grossProceeds>27080</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/15/2025</saleDate>
      <amountOfSecuritiesSold>2000</amountOfSecuritiesSold>
      <grossProceeds>27820</grossProceeds>
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    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/14/2025</saleDate>
      <amountOfSecuritiesSold>2500</amountOfSecuritiesSold>
      <grossProceeds>36425</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/13/2025</saleDate>
      <amountOfSecuritiesSold>11250</amountOfSecuritiesSold>
      <grossProceeds>163012.5</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/02/2025</saleDate>
      <amountOfSecuritiesSold>33750</amountOfSecuritiesSold>
      <grossProceeds>479925</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>05/01/2025</saleDate>
      <amountOfSecuritiesSold>2500</amountOfSecuritiesSold>
      <grossProceeds>36075</grossProceeds>
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    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/31/2025</saleDate>
      <amountOfSecuritiesSold>25000</amountOfSecuritiesSold>
      <grossProceeds>333750</grossProceeds>
    </securitiesSoldInPast3Months>
    <securitiesSoldInPast3Months>
      <sellerDetails>
        <name>Azzurro Capital Inc.</name>
        <address>
          <com:street1>c/o Sovereign Management Limited</com:street1>
          <com:street2>PO Box 564 Sovereign Place</com:street2>
          <com:city>Gibraltar</com:city>
          <com:stateOrCountry>J1</com:stateOrCountry>
          <com:zipCode>GX11 1AA</com:zipCode>
        </address>
      </sellerDetails>
      <securitiesClassTitle>Common Stock</securitiesClassTitle>
      <saleDate>03/24/2025</saleDate>
      <amountOfSecuritiesSold>32500</amountOfSecuritiesSold>
      <grossProceeds>465725</grossProceeds>
    </securitiesSoldInPast3Months>
    <noticeSignature>
      <noticeDate>06/20/2025</noticeDate>
      <signature>/s/ Ralph Bartel, Authorized Signatory</signature>
    </noticeSignature>
  </formData>
</edgarSubmission>
