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Greetings Professor Thompson,
Thank you for posting your inquiry to the History Hub!
Unfortunately, we're unaware of any complete listing of free Blacks residing in antebellum Chicago. Most likely your best bet will be to review federal and state census records. The most complete listing of federal and state census records for Illinois can be viewed online via Ancestry.com. Ancestry is a subscription-based website, but your university library may provide access to the site. You can find it here Ancestry® | Genealogy, Family Trees & Family History Records
We examined Tony Burroughs' guide "Black Roots: A Beginner's Guide to Tracing the African American Family Tree" for any references to such a listing without success. We're also unsure that all African-Americans were required to carry certificates, or freedom papers of some sort, although freed former slaves most likely would have documentation regarding their status.
In Illinois, you may wish to contact the Chicago History Museum https://www.chicagohistory.org/collections/explore-our-research-collections/, the Chicago Public Library's Special Collections Special Collections | Chicago Public Library the Illinois State Archives Illinois State Archives, and lastly, the Abraham Lincoln Presidential Library and Museum: Library
The Chicago area also is home to a dedicated and enthusiastic group of genealogical researchers: The Afro-American Genealogical and Historical Society of Chicago. You can contact them at AAGHSC
We hope these resources may be useful in your research.
Thank you for contacting the History Hub!