I have a love/ hate relationship with the city. I grew up on the NW side of the city (Norwood Park/ Edison Park). Within a couple of hours and without a car I could go ANYWHERE (either airport, the loop, Evanston, Navy Pier); and I've had more annoyances here and there but in all the public transportation is awesome.
Just recently the city has hit its Beer Awakening. Metropolitan, Goose Island, Piece, Half Acre, and Revolution are all in the city. Another great plus.
It's been said before (and hopefully it will change with the changing of the guard/ Daley), but it's corrupt. And let's be specific. It's nepotism. I grew up in an area where people only w/ HS diploma were city employees and made near a $100k; and the only way to get in was to be a Daley crony. It's hard to believe that so many people are sucking off the city tit that they don't want to see a change, but that's how Daley was able to keep himself nice and secure.
Traffic also blows, but I don't think NY or LA are any better (actually have heard that LA is worse).