Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flappers, dancing the Charleston to the music of Cole Porter and George Gershwin. It's a night out in Chicago you'll never forget!
- All taxes, fuel surcharges and service fees included
- Tour is wheelchair accessible
- All entrance fees included
- Dinner included
Entering Tommy Gun's Garage through the "El" tracks, you'll swear you've time traveled back to the 1920s and the era of speakeasies! You'll see silent movies playing, memorabilia from the 1920s, the Boss's 1928 Model A Ford car, a replica of the wall from the St. Valentines Day Massacre and pictures of gangsters and coppers from those times.
The "Mugs" and "Molls" dance and sing to Cole Porter, George Gershwin, Fats Waller, Duke Ellington and more ... All played by Chicago's Sinfully Orchestra.
After a great dinner of pasta, steak, fish or chicken, join "Vito", "Gloves", the "Mugs" and the "Molls" for non-stop comedy and dangerous fun, as they entertain you with singing, dancing, and a LOT of audience participation!
You'll be raided by the cops, complete with raid sirens and flashing lights. Perhaps you'll even be pulled up onstage to perform a hilarious sobriety test given by Officer Murphy, and be "interviewed" by Vito!
Valentine's Day Weekend
During Valentine's weekend the dinner show will include a historical re-enactment of the Saint Valentine's Day Massacre, the 1929 murder of mob members part of the conflict between two criminal gangs in Chicago: the Italian gang led by Al Capone and the Irish Gang led by Bugs Moran.
Recent Photos of this Tour
Select a month to view a calendar of availability and departure details.
Tommy Gun's Garage
- Wednesday - 6:00pm
- Thursday - 6:00pm
- Friday - 7:00pm
- Saturday - 6:00pm
- Sunday - 5:30pm
Valentine's Day Weekend:
- February 13 - 7pm
- February 14 - 5pm
- February 15 - 1pm & 5:30pm
Click the link below to check pricing & availability on your preferred travel date. Our pricing is constantly updated to ensure you always receive the lowest price possible.
Tommy Gun's Garage Dinner and Show
- Local taxes
- Alcoholic drinks (available to purchase)
- Hotel pickup and drop off
- Confirmation of this show will be received within 48 hours of booking, subject to availability
- Wheelchair accessible
- Adult pricing applies to all travelers
- All kids 12 years and under receive a free Tommy Gun's Garage souvenir!
Sample menu (subject to change):
Lasagna with Meat or Marinara Sauce
Fish and Pork:
Salmon or Pork Chops
Chicken with Marsala or Lemon Herb Sauce
Ice Cream (served at intermission)
(Dinner also includes soup or salad, vegetable, potato, dessert and coffee, tea or soda)
New Year's Eve Show includes champagne toast and dancing
If you cancel between 3 and 6 day(s) in advance of the scheduled departure, there is a 50 percent cancellation fee.
If you cancel within 2 day(s) of the scheduled departure, there is a 100 percent cancellation fee.
Reviewed by: Corycat, Canada, August 2016
This was an amazing amazing time, the mob boss was awesome! You felt like you were back in the mob days, our waitress was awesome! Staff was great! The food was so good!! So much food!! So worth the time to go!! LOVED IT
Reviewed by: Keterri B, July 2016
This dinner and show was amazing. We loved it. So much fun.