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Get away from Rush and Division and go to some more local type bars. Most interesting place: Southport Lanes - manual set bowling pins, pool hall - really neat place, like an upscale pool hall.
After close: Weiner Circle - hot dogs in Lincoln park I think. In playboy last month as best after hours food. Food sucks, but it is a crazy time.
Matchbox - chicago's smallest/narrowest bar - really classy. Great for afterdinner drinks - good martini's.
go to Metromix.com - and search - I used that site and you can find great stuff. Have fun.
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