Great Idea, I Love diving, just not going to spend time/$ to dive a quarry.
Have always wanted to dive Lake Michigan or other Great Lakes.
From the limited research I've done, nearest 'decent' wreck diving to Chicago is off of Milwaukee. Most dives require drysuit which I've never used.
The other place of interest I've looked at is diving near Munising, Michigan:
http://www.exploringthenorth.com/scuba/diving.html
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