please forgive a selfish and non-music thread, but is anyone from or familiar with the city? i've been a few times but i always kind of end up in wicker park just browsing record and book stores. if you know of any good dive bars, low-key blues/jazz clubs, restaurants or other parts of town worth exploring, tell me! i will be there next week for about 5 days and have almost nothing to do!
at the very least, i should probably catch a cubs game, huh?
I lived in Chicago two and half years. I was a graduate student, so I didn't always have a lot of time, and your questions remind me of all the Chicago exploring I never got to do!
My entertainment centered around Wicker Park, which is still a cool place to catch mostly indie rock / hard rock shows. The neighborhood is changing though, and some cooler places have shut down and are often being replaced with ugly banks. Just South of Wicker Park on Division Street are a couple of low-key jazz clubs that I think are still in business.
I would look into the Edgewater/Uptown neighborhood, which has a variety of music venues and is interesting to explore. A show at the Metro in Wrigleyville is always a good experience, combine that with a Cubs game and you can have quite a day. If you want to go really far North and you like Indian food, try Devon Avenue for all sorts of exotic restaurants.
There are also some authentic blues places off the beaten path, but unfortunately I never had the chance to go to much of them. On a small strip of North Halstead road there are two blues clubs across from each other, Blues on Halstead and Kinston Mines. Rosa's Blues Longue on the Far West side of Chicago could be good, as well as numerous South Side places.
It's not a strict blues club, but Abbey Pub is also a nice place.
Have fun! I bet Harold Wexler would have a lot more ideas.
Actually, I don't have too many more ideas - I'm kind of woefully behind on my explorations of the city, considering that I've lived here all but two years of my life. I tend to stick to the same places a lot.
One that hasn't come up in this thread: there's a terrific independent record store in Lincoln Square, right off the Western L stop, called Laurie's Planet of Sound. It's one of the few smaller record stores in town that's managed to survive the massive bloodletting in the bricks-and-mortar industry over the last couple of years.