5 star rating: Highly Recommended 106 Reviews

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  • Location: Chicago, Illinois
  • Duration:  3 hours (approx.)

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!


  • Tommy Gun's Garage
  • Experience dinner theater in Chicago
  • Be transported back to the roaring twenties with gangsters and flappers
  • Non-stop comedy and dangerous fun, singing, dancing, and a LOT of audience participation!

Recent Photos of This Tour

What You Can Expect

Tommy Gun's Garage Dinner and Show

Tommy Gun's Garage Dinner and Show

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.


Sample menu (subject to change):

Lasagna with Meat or Marinara Sauce

Prime Rib

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

Customer Reviews

5 star rating: Highly Recommended August 2015

Brilliant show. Great interaction with the audience. Personally meet the characters in the show as they come around to your table and introduce themselves and insult you. This evening is a must for your visit to Chicago. 3 Hours of food, drink and brilliant entertainment Well worth the 70

5 star rating: Highly Recommended August 2015


5 star rating: Highly Recommended July 2015

Great show! Very entertaining! Performers were also waiters! Everyone came to our table and talked with us. Very personable! Food was great! My teenagers really enjoyed it! And they chose my husband for a skit. Very fun. Will do it again !

5 star rating: Highly Recommended June 2015

The show was very entertaining and the food was great. The staff was talented and lots of fun!

5 star rating: Highly Recommended June 2015

Such a great night! I would recommend this to everybody!
The night was a show from start to finish. The bar is reasonably priced. The mood is relaxed and the staff are all so warm and welcoming. I'm surprised this isn't in a tour book.

5 star rating: Highly Recommended May 2015

loved the show!!! Crew was great. I am in love with MUSCLE!!!

5 star rating: Highly Recommended May 2015

Had a great time! Delicious dinner and a fun show - singing, dancing, amazing magic act. It's one of the great memories we made on our first 9but not last trip to Chicago.

5 star rating: Highly Recommended March 2015

This tour was amazing!

5 star rating: Highly Recommended February 2015

Tommy Gun's is a definite must visit for anyone staying in Chicago. Everyone involved in this production are wonderful, an extremely hard working team. A big thanks to Sadie who looked after us so well.

5 star rating: Highly Recommended November 2014

Excellent - great show, good food but most of all, lovely people who run it - wasn't well in second half of show, members of the cast helped me out, escorted my mother (holding her arm) to a taxi they had ordered - very kind, genuine people. Thanks so much from Wales x

From USD $ 64.99

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Tour code: 3918DINNERSHOW


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