Chicago is a no-nonsense town with a bar on every corner, and often 3 or 4 in-between. It's got some of the best blues in the country. It's got pizza that weighs about 3 lbs a slice. The citizens take beer very, very seriously. It's a world-class city with a feel unlike anywhere else. There's not a lot of pretense there-- Chicago is legit.
Love it or hate it, you gotta spend a bit of time there. If you do-- go up to Wrigleyville to the Kingston Mines blues club. Prepare to be blown away.