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Second City is, of course, the granddaddy of comedy-themed date nights, but good times can also be had for fewer dollars (and fewer people from Iowa) at indie comedy venues like the Cornservatory or regular stand-up nights like Timothy O’Toole’s “Comedians You Should Know” (see full list here).

Fortunately, comedy shows tend to be pretty cheap dates.

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There is perhaps no easier summer date than at one of Chicago's fine tiki bars: immediately fun and tropical, the only way you can screw this up is to start talking politics.

The fun part is, Wrigley and Guaranteed Rate couldn’t be more different, so there’s a ballpark experience for everyone.

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