In the book "Chicago and Cook County Sources: A Genealogical and Historical Guide" by Loretto Dennis Szucs (publish date 1986), "Irish Sources" are recommended that may find helpful to you; are as follows:
Irish American Heritage Center Chicago
Chicago Irish Ancestry (CIA) c/o Newberry Library Chicago
The Chicago Genealogical Society
The Irish American News Chicago
Hope this is helpful.
See "The Jule Rose Conroy Collection" at : Beverly Branch of the Chicago Public Library
You could visit some South Side Irish neighborhoods and maybe learn about the history from the people themselves.
There is a tremendous amount of information on line. Also, The University of Notre Dame has a large collection on Irish American history. On the Internet type in the words, "Canaryville" or "Bridgeport, Chicago". Go to St. Gabrial's Church located in Canaryville. Call Gaelic Park in Oak Forest, Il. They may have some sources. Also the Chicago Historical Society has an extensive collection on immigrant groups.
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