As bad as Illinois is, at least it’s not Ohio
I'd say the biggest selling point for me is the area, outdoors, and culture around the Great Lakes (well, Superior, Michigan, and Huron at least - I haven't been to the others). With that in mind, if I could pick to move today, I'd move north - Wisconsin or Michigan, either. Yeah winter is cold, but that's why they invented coats. If it must be Northern Illinois, stay out of Cook County if you can. I'm in the NW burbs and we do have nice amenities, yet I'm far out enough to not have to deal with too much Chicago crap.
Aviation here is lighter than some of the meccas like FL, AZ, Denver, etc - but it's supported and respected. You won't find advocacy groups trying to shutter airports. Rather, the sad news is when no one sticks around to support airports and they get into disrepair or get sold off (C81, C02, 5K6, etc). As far as hangars - avoid the Chicago area. Airports that have availability are KPWK ($550 min), KDKB, KUGN, KENW, and maybe C81, 10C, C77. Anything closer has waitlists - KDPA is full, 06C has an 8 year waitlist. Sometimes one will come up for sale at 3CK. Plenty of community hangars and FBOs here though.. just need $$$$$.