And since nothing says love like mass murder, I'll start with the Tommy Gun's Garage re-enaction of the St. Valentine's Day Massacre!
On February 14, 1929 seven members of the Bugs Moran gang were brutally murdered in an event that made the country realize just how bad the Prohibition Era Chicago gang wars had gotten. Being that Tommy Gun's Garage is Prohibition Era speakeasy/dinner theater restaurant, they have reenacted this event every year for over 20 years.
After you experience the classic Tommy Gun's revue – skits, singing and dancing hosted by Vitto, “da gangsters” and “da flappers” – sit back and watch this display of Chicago history. One by one, actors portraying the unlucky men walk on to the scene, set to resemble the SMC Cartage Company where the tragic event occurred. (The garage has long since been torn down, but you can still visit the site at 2122 N Clark St.) As the narrator tells each man's story, actors portraying Al Capone's men dressed as "coppers" on a mock raid begin arresting the gangsters. But instead of cuffing them, they line them up and let the bullets fly. Whereas is was never proven that Al Capone was behind the massacre, it has always been assumed that this was a message from Capone to his long-time rival, Bugs Moran.
The show itself is great for families with older children (10-years old and up) but the re-enactment is extremely realistic, so leave the kids at home. It's so realistic, in fact, that it's been filmed for numerous St. Valentine's Day Massacre documentary films and television shows, including the History Channel.
The show runs throughout Valentine's Day weekend, and seating is limited so make a reservation. Ticket pricing is $60 - $75 and includes a multi-course dinner and the show.