I bet that Skydive place Chicago is on your no fly zone...isn't it closer to the Wisconsin border than the city? I don't remember exactly where it is. I have friends that have gone there several times. their last jump was part of their babymoon. She was like 4 or 5mo pregnant at the time.
There are few around. Skydive Chicago is in Ottawa (I used to live across the highway from their field). The one that I'm most wary of is Hinkley though. It sits in a spot that I fly through fairly often.