I think Chicago and IL are slept on in general but have a lot of long term positives. IL (thanks to Pritzker and a post-Magidan House) is starting to shore up fiscally, Lake Michigan (for both recreation and water supply) and a decent public transit system make it very appealing.
Chicago is a good choice but a lot of people wouldn't be able to tolerate the winter.
It can be brutal to get through. The bonus on the other side of it is that the summers are amazing with all of the public beaches and summer events going on.