If your ancestor was a prominent Chicago citizen you might try The Chicago Historical Society. Otherwise, you are talking about genealogical research and your best bet will be to get in touch with others who may be researching the same family lines. Go online to USGenWeb for Cook CO IL, read the query postings, and post a message of your own. Also, go to GenForum where surname message boards can help you locate others researching your ancestors. Be sure to check all possible surnames including maiden names, names of other spouses, etc.. Someone may have pictures---and information---to share.
You can try the site "Dead Fred" www.deadfred.com. This site is searchable by surname and/or locality. It is a user contributed database aiding in reconnection people with lost photos of relatives.
You can also try message boards at ancestry.com and post inquiries.
Hope that helps!
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