Chicago is awesome. I live in Wrigleyville and it's a great neighborhood - there is a ton of things to do no matter what your interests are. The only downfall is the weather. It does get too cold in the winter, although this winter has been surprisingly warm.
The summers are great, though. The beach is awesome - there is beach volleyball, an outside gym right on the beach, the boat house is an outdoor restaurant and bar. It's always a big party.
If Chicago was in a warmer climate, it would be one of the best cities on earth.