<?xml version="1.0"?>
<edgarSubmission>

    <schemaVersion>X0705</schemaVersion>

    <submissionType>D/A</submissionType>

    <testOrLive>LIVE</testOrLive>

    <primaryIssuer>
        <cik>0001545430</cik>
        <entityName>Chicagoland Street Retail DST</entityName>
        <issuerAddress>
            <street1>2901 BUTTERFIELD ROAD</street1>
            <city>OAK BROOK</city>
            <stateOrCountry>IL</stateOrCountry>
            <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
            <zipCode>60523</zipCode>
        </issuerAddress>
        <issuerPhoneNumber>630-218-4916</issuerPhoneNumber>
        <jurisdictionOfInc>DELAWARE</jurisdictionOfInc>
        <issuerPreviousNameList>
            <value>None</value>
        </issuerPreviousNameList>
        <edgarPreviousNameList>
            <value>None</value>
        </edgarPreviousNameList>
        <entityType>Other</entityType>
        <entityTypeOtherDesc>Delaware Statutory Trust</entityTypeOtherDesc>
        <yearOfInc>
            <withinFiveYears>true</withinFiveYears>
            <value>2012</value>
        </yearOfInc>
    </primaryIssuer>

    <relatedPersonsList>
        <relatedPersonInfo>
            <relatedPersonName>
                <firstName>Capital Corporation</firstName>
                <lastName>Inland Private</lastName>
            </relatedPersonName>
            <relatedPersonAddress>
                <street1>2901 Butterfield Road</street1>
                <city>Oak Brook</city>
                <stateOrCountry>IL</stateOrCountry>
                <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                <zipCode>60523</zipCode>
            </relatedPersonAddress>
            <relatedPersonRelationshipList>
                <relationship>Promoter</relationship>
            </relatedPersonRelationshipList>
            <relationshipClarification></relationshipClarification>
        </relatedPersonInfo>
        <relatedPersonInfo>
            <relatedPersonName>
                <firstName>Retail, L.L.C.</firstName>
                <lastName>Chicagoland Street</lastName>
            </relatedPersonName>
            <relatedPersonAddress>
                <street1>2901 Butterfield Road</street1>
                <city>Oak Brook</city>
                <stateOrCountry>IL</stateOrCountry>
                <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                <zipCode>60523</zipCode>
            </relatedPersonAddress>
            <relatedPersonRelationshipList>
                <relationship>Promoter</relationship>
            </relatedPersonRelationshipList>
            <relationshipClarification></relationshipClarification>
        </relatedPersonInfo>
        <relatedPersonInfo>
            <relatedPersonName>
                <firstName>Retail Exchange, L.L.C.</firstName>
                <lastName>Chicagoland Street</lastName>
            </relatedPersonName>
            <relatedPersonAddress>
                <street1>2901 Butterfield Road</street1>
                <city>Oak Brook</city>
                <stateOrCountry>IL</stateOrCountry>
                <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                <zipCode>60523</zipCode>
            </relatedPersonAddress>
            <relatedPersonRelationshipList>
                <relationship>Promoter</relationship>
            </relatedPersonRelationshipList>
            <relationshipClarification></relationshipClarification>
        </relatedPersonInfo>
        <relatedPersonInfo>
            <relatedPersonName>
                <firstName>Keith</firstName>
                <lastName>Lampi</lastName>
            </relatedPersonName>
            <relatedPersonAddress>
                <street1>2901 Butterfield Road</street1>
                <city>Oak Brook</city>
                <stateOrCountry>IL</stateOrCountry>
                <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                <zipCode>60523</zipCode>
            </relatedPersonAddress>
            <relatedPersonRelationshipList>
                <relationship>Executive Officer</relationship>
            </relatedPersonRelationshipList>
            <relationshipClarification>Mr. Lampi is the Senior Vice President of Inland Private Capital Corporation, the Member of Chicagoland Street Retail Exchange, L.L.C., the Signatory Trustee of Chicagoland Street Retail DST.</relationshipClarification>
        </relatedPersonInfo>
    </relatedPersonsList>

    <offeringData>
        <industryGroup>
            <industryGroupType>Other Real Estate</industryGroupType>
        </industryGroup>
        <issuerSize>
            <revenueRange>Decline to Disclose</revenueRange>
        </issuerSize>
        <federalExemptionsExclusions>
            <item>06</item>
        </federalExemptionsExclusions>
        <typeOfFiling>
            <newOrAmendment>
                <isAmendment>true</isAmendment>
                <previousAccessionNumber>0001545430-12-000004</previousAccessionNumber>
            </newOrAmendment>
            <dateOfFirstSale>
                <value>2012-03-28</value>
            </dateOfFirstSale>
        </typeOfFiling>
        <durationOfOffering>
            <moreThanOneYear>false</moreThanOneYear>
        </durationOfOffering>
        <typesOfSecuritiesOffered>
            <isOtherType>true</isOtherType>
            <descriptionOfOtherType>Beneficial interests in Delaware Statutory Trust reflecting beneficial interests in real estate.</descriptionOfOtherType>
        </typesOfSecuritiesOffered>
        <businessCombinationTransaction>
            <isBusinessCombinationTransaction>false</isBusinessCombinationTransaction>
            <clarificationOfResponse></clarificationOfResponse>
        </businessCombinationTransaction>
        <minimumInvestmentAccepted>25000</minimumInvestmentAccepted>
        <salesCompensationList>
            <recipient>
                <recipientName>Inland Securities Corporation</recipientName>
                <recipientCRDNumber>15807</recipientCRDNumber>
                <associatedBDName>Inland Securities Corporation</associatedBDName>
                <associatedBDCRDNumber>15807</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>2901 Butterfield Road</street1>
                    <city>Oak Brook</city>
                    <stateOrCountry>IL</stateOrCountry>
                    <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                    <zipCode>60523</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>IL</state>
                    <description>ILLINOIS</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Robert S. Smith</recipientName>
                <recipientCRDNumber>1412333</recipientCRDNumber>
                <associatedBDName>Concorde Investment Services, LLC</associatedBDName>
                <associatedBDCRDNumber>151604</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>8705 SW Nimbus Avenue, Suite 260</street1>
                    <city>Beaverton</city>
                    <stateOrCountry>OR</stateOrCountry>
                    <stateOrCountryDescription>OREGON</stateOrCountryDescription>
                    <zipCode>97008</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>OR</state>
                    <description>OREGON</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>James K. Johnston</recipientName>
                <recipientCRDNumber>1689783</recipientCRDNumber>
                <associatedBDName>Arete Wealth Management, LLC</associatedBDName>
                <associatedBDCRDNumber>44856</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>775 Ridge Lake Boulevard, Suite 150</street1>
                    <city>Memphis</city>
                    <stateOrCountry>TN</stateOrCountry>
                    <stateOrCountryDescription>TENNESSEE</stateOrCountryDescription>
                    <zipCode>38120</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>TN</state>
                    <description>TENNESSEE</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Clovis M. Morrison</recipientName>
                <recipientCRDNumber>1730240</recipientCRDNumber>
                <associatedBDName>Centaurus Financial, Inc.</associatedBDName>
                <associatedBDCRDNumber>30833</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>2570 FM 407, Suite 210</street1>
                    <city>Highland Village</city>
                    <stateOrCountry>TX</stateOrCountry>
                    <stateOrCountryDescription>TEXAS</stateOrCountryDescription>
                    <zipCode>75077</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>TX</state>
                    <description>TEXAS</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Nathaniel M. Kuhn</recipientName>
                <recipientCRDNumber>4624143</recipientCRDNumber>
                <associatedBDName>Investacorp, Inc.</associatedBDName>
                <associatedBDCRDNumber>7684</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>1100 West Northwest Highway, Suite 114</street1>
                    <city>Mt. Prospect</city>
                    <stateOrCountry>IL</stateOrCountry>
                    <stateOrCountryDescription>ILLINOIS</stateOrCountryDescription>
                    <zipCode>60056</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>IL</state>
                    <description>ILLINOIS</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Dwight K. Kay</recipientName>
                <recipientCRDNumber>5376903</recipientCRDNumber>
                <associatedBDName>Independent Financial Group, LLC</associatedBDName>
                <associatedBDCRDNumber>7717</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>1717 Palacious Drive</street1>
                    <city>San Pedro</city>
                    <stateOrCountry>CA</stateOrCountry>
                    <stateOrCountryDescription>CALIFORNIA</stateOrCountryDescription>
                    <zipCode>90274</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>CA</state>
                    <description>CALIFORNIA</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Kyle H. Imholte</recipientName>
                <recipientCRDNumber>5448950</recipientCRDNumber>
                <associatedBDName>1st Global Capital Corp.</associatedBDName>
                <associatedBDCRDNumber>30349</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>1215 Washington Avenue South</street1>
                    <city>Detroit Lakes</city>
                    <stateOrCountry>MN</stateOrCountry>
                    <stateOrCountryDescription>MINNESOTA</stateOrCountryDescription>
                    <zipCode>56502</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>MN</state>
                    <description>MINNESOTA</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Vic V. Mullet</recipientName>
                <recipientCRDNumber>4656976</recipientCRDNumber>
                <associatedBDName>Centaurus Financial, Inc.</associatedBDName>
                <associatedBDCRDNumber>30833</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>2822 3rd Avenue North, Suite 204</street1>
                    <city>Billings</city>
                    <stateOrCountry>MT</stateOrCountry>
                    <stateOrCountryDescription>MONTANA</stateOrCountryDescription>
                    <zipCode>59101</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>MT</state>
                    <description>MONTANA</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Joseph M. Insalaco</recipientName>
                <recipientCRDNumber>2978175</recipientCRDNumber>
                <associatedBDName>Triad Advisors, Inc.</associatedBDName>
                <associatedBDCRDNumber>25803</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>1311 Jacksons Avenue, Suite 3A</street1>
                    <city>Long Island City</city>
                    <stateOrCountry>NY</stateOrCountry>
                    <stateOrCountryDescription>NEW YORK</stateOrCountryDescription>
                    <zipCode>11101</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>NY</state>
                    <description>NEW YORK</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Samuel C. Bridgers, III</recipientName>
                <recipientCRDNumber>1243406</recipientCRDNumber>
                <associatedBDName>VSR Financial Services, Inc.</associatedBDName>
                <associatedBDCRDNumber>14503</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>230 Marter Avenue</street1>
                    <city>Moorestown</city>
                    <stateOrCountry>NJ</stateOrCountry>
                    <stateOrCountryDescription>NEW JERSEY</stateOrCountryDescription>
                    <zipCode>08057</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>NJ</state>
                    <description>NEW JERSEY</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Robert A. Burch, Sr.</recipientName>
                <recipientCRDNumber>1045257</recipientCRDNumber>
                <associatedBDName>Proequities, Inc.</associatedBDName>
                <associatedBDCRDNumber>15708</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>2694 Bishop Drive, Suite 290</street1>
                    <city>San Ramon</city>
                    <stateOrCountry>CA</stateOrCountry>
                    <stateOrCountryDescription>CALIFORNIA</stateOrCountryDescription>
                    <zipCode>94583</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>CA</state>
                    <description>CALIFORNIA</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Timothy J. Sherer</recipientName>
                <recipientCRDNumber>833618</recipientCRDNumber>
                <associatedBDName>J.P. Turner &amp; Company, L.L.C.</associatedBDName>
                <associatedBDCRDNumber>43177</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>1754 Technology Drive, Suite 236</street1>
                    <city>San Jose</city>
                    <stateOrCountry>CA</stateOrCountry>
                    <stateOrCountryDescription>CALIFORNIA</stateOrCountryDescription>
                    <zipCode>95110</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>CA</state>
                    <description>CALIFORNIA</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>David M. Nelson</recipientName>
                <recipientCRDNumber>2120855</recipientCRDNumber>
                <associatedBDName>Cambridge Investment Research, Inc.</associatedBDName>
                <associatedBDCRDNumber>39543</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>880 13th Avenue North</street1>
                    <city>Clinton</city>
                    <stateOrCountry>IA</stateOrCountry>
                    <stateOrCountryDescription>IOWA</stateOrCountryDescription>
                    <zipCode>52732</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>IA</state>
                    <description>IOWA</description>
                    <state>UT</state>
                    <description>UTAH</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Kenneth M. Nelson</recipientName>
                <recipientCRDNumber>3231051</recipientCRDNumber>
                <associatedBDName>Cambridge Investment Research, Inc.</associatedBDName>
                <associatedBDCRDNumber>39543</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>880 13th Avenue North</street1>
                    <city>Clinton</city>
                    <stateOrCountry>IA</stateOrCountry>
                    <stateOrCountryDescription>IOWA</stateOrCountryDescription>
                    <zipCode>52732</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>IA</state>
                    <description>IOWA</description>
                    <state>UT</state>
                    <description>UTAH</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>Warren W. Woon</recipientName>
                <recipientCRDNumber>4115548</recipientCRDNumber>
                <associatedBDName>VSR Financial Services, Inc.</associatedBDName>
                <associatedBDCRDNumber>14503</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>745 Fort Street, Suite 1614</street1>
                    <city>Honolulu</city>
                    <stateOrCountry>HI</stateOrCountry>
                    <stateOrCountryDescription>HAWAII</stateOrCountryDescription>
                    <zipCode>96813</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>HI</state>
                    <description>HAWAII</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
        </salesCompensationList>
        <offeringSalesAmounts>
            <totalOfferingAmount>3426177</totalOfferingAmount>
            <totalAmountSold>3360218</totalAmountSold>
            <totalRemaining>65959</totalRemaining>
            <clarificationOfResponse></clarificationOfResponse>
        </offeringSalesAmounts>
        <investors>
            <hasNonAccreditedInvestors>false</hasNonAccreditedInvestors>
            <totalNumberAlreadyInvested>16</totalNumberAlreadyInvested>
        </investors>
        <salesCommissionsFindersFees>
            <salesCommissions>
                <dollarAmount>239832</dollarAmount>
                <isEstimate>true</isEstimate>
            </salesCommissions>
            <findersFees>
                <dollarAmount>0</dollarAmount>
            </findersFees>
            <clarificationOfResponse>This response is based on the assumption that the full amount of the potential sales commissions will be earned and paid.</clarificationOfResponse>
        </salesCommissionsFindersFees>
        <useOfProceeds>
            <grossProceedsUsed>
                <dollarAmount>386156</dollarAmount>
                <isEstimate>true</isEstimate>
            </grossProceedsUsed>
            <clarificationOfResponse></clarificationOfResponse>
        </useOfProceeds>
        <signatureBlock>
            <authorizedRepresentative>false</authorizedRepresentative>
            <signature>
                <issuerName>Chicagoland Street Retail DST</issuerName>
                <signatureName>/s/ Keith Lampi</signatureName>
                <nameOfSigner>Keith Lampi</nameOfSigner>
                <signatureTitle>Senior Vice President of the Member of the Signatory Trustee</signatureTitle>
                <signatureDate>2012-06-21</signatureDate>
            </signature>
        </signatureBlock>
    </offeringData>
</edgarSubmission>
