bugtooth would be your best but since swapping his TLR for a Busa he doesn't drop in much any more. You might see if you can find his e-mail though. IN the meantime maybe someone else will speak up. There are some good clubs, music, museums, etc. there. It's been over 10 years since I lived there so I won't even try to pretend I have a clue anymore.
Heritage park, Buckingham fountain, Shedd Aquarium, Museum of Science & Industry, Museum of Natural History, Art Institute (check out the lion statues at the main entrance), Museum of Modern Art, B.L.U.E.S. club, Kingston Mines Blues Club on Halsted, the 95'th restaurant atop the Hancock, Chinatown for dim-sum, whoever's playing at the Auditorium Thearer (neat interior architecture), New World Theater (huge outdoor music venue), Navy Pier (entertainment area now, take a boat ride on the lake), a musical at Chicago Theater, Taste of Chicago festival (seasonal), Blues Fest (seasonal), Wrigley Field for Chicago Cubs baseball, Mother's (a bar on Division) UNO's Chicago-style Pizza, Michigan Avenue miracle mile. Short drive to Milwaukee for October Fest (seasonal). Depends what you're interested in.
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