Egad - don't forget to check in at the Old Town School of Folk Music.. the halls resound. I was there 10 minutes (to meet a friend) and dragged in to be audience/guinea pig for a dance teacher...nice friendly place. I even think they're online by now but you'll have to find out through www.google.com. Friendliest dern place in the city. Elaine in Michigan though 20+ years in Chicago.
Also Hogeye Music in Evanston does house concerts (teeny place, maybe room for 30 close friends) occasionally with dynamite "coffee bean" shop just down the block. Easy to get to on the "el", just (going north towards Howard)get on the Evanston train, then off at Central hang a left about 1 block.
Museum of Broadcast History has a station in the downtown Chicago Public library, complete with recreation of "fibber McGee's closet" if you're interested in old time radio. BTW, Jenny Armstrong lives in Evanston (or did) has a studio in the Evanston Arts Center, with a unique clause - no bagpipe playing...(well, as of 2 years ago when I left).