Simon's Tavern

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Steeped in Chicago history, the original 1930s mahogany bars and back bars are still the focal points at this Andersonville hangout. The owner became a bootlegger during Prohibition, and cashed people's paychecks while sitting in a bullet-proof booth, which is still there. Mosaic tables dot the space, which is surrounded with wood paneling. A mural, painted in the 1940s, depicts the owner and his friends partying after a deer hunt. After the death of the original owner, his son owned the bar until 1994. If you ask, the current owner may even take you on a tour. This is a very friendly place, where the clientele are folks that go to socialize and have interesting conversation, not get falling-down drunk.

Simon's Tavern is located at 5210 N. Clark St. in Chicago's Andersonville Neighborhood