If hell could freeze over, it would be Chicago. Horrible public transportation - CTA sucks, if moving there, I suggest you take a car. The weather is miserable, and not just the winters. Oh yeah, and check out the grey, endless flat landscape, inspiring isn't it?
Oh, and don't get me started on the local politics, corruption at its worst. Its most famous gangster, Al Capone, was actually from Brooklyn, moved to Chicago and realized how easy it would be to take advantage of its people.
After hearing so much about how great Chicago was from friends, I came to find out that none of them actually lived in the city. They all live in the fucking suburbs. Hmm, I wonder why?
I must say though, the only redeeming feature of that city is lake Michigan, but I'm sure if given the chance they'll find a way to screw that up too.
Rudyard Kipling on Chicago - "Having seen it, I urgently desire never to see it again."