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OK, here are some of my thoughts on things to do if your are under 21.
Bars and clubs are probably out.
Cubs or Sox game. Navy Pier has got bands in the summer. Beaches. Rent a bike and bike up/down lakeshore. Check out some of the summer block parties/concerts at metromix.com. (there is always some sort of festival going on) Some of the House of Blues shows are all ages, I think. There's theater, if that's something you are not opposed to going to. There are cruises on the lake, many are off the pier. Hancock building or Sears tower, going to Chinatown or Greektown for food and sightseeing - although I would go in a group. There are movie theaters downtown.
Hope this helps at least a little. It has been three years since I was 20, and when I was in Chicago I had an id saying I was a little older.
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