Tommy Gun's Garage, Chicago

It's still the 1920s inside Tommy Gun's Garage Dinner Theater, and they're openly flouting Prohibition laws. The venue features a full bar serving a variety of hooch, a flapper- and gangster-studded comedy and theater show, and waiters who drive 1928 Model Fords (or who at least tell you they do). It feels a bit like a perfectly preserved speakeasy.

The theater really is steeped in history, just not 90 or so years' worth of it. Originally founded by a Chicago policeman in 1987, it is the longest-running dinner theater show in Chicago. It's interactive, too, which means guests do more than just eat dinner and watch the show. They also interact with the performers, who are always in character as a flapper, gangster, or fringe salesman.