Oh I forgot, Chicago actually has some pretty interesting history, and if you're into architecture, museums, and theater, it is a great place.
What bums me out about Chicago:
Endless suburbs, the suburbs just suck in general, far away from wilderness, lack of cool roads, far away from good skiing, horrible attitudes of most of the people.
#1 rant: If you want to live somewhere cool, good luck parking your car and not having it ruined/vandalized. You can get a garage, but you better be lucky or rich to be able to afford it.