Wrigleyville,lots to eat,many good music venues.Google "the reader" a chicago,entertainment newspaper.It tells it all.I live an hour north ,but dont get down there much anymore.Was there any thing specific,you were looking for? PM if ya want.
Another good area to visit might be Lincoln Square, and although they are way over-trendy: Wicker Park, Logan Square and River North neighborhoods offer some cool stuff, too.
Museum of Science and Industry has a CSI exhibit going on where you can solve your own murder case, or something? I don't know, I've heard some weird stuff from people who went to it.
There's always a bunch of street festivals and mini outdoor concerts going on during any given weekend in the summer. Chicago Reader is the best place, as Seamus said, to get the scoop on all that - Concerts, restaurants, theater, stores, etc.
