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Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.


  • Experience dinner theater in Chicago
  • Travel back to the roaring twenties with gangsters and flappers
  • Non-stop comedy and dangerous fun, singing, dancing, and a lot of audience participation

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What You Can Expect

Tommy Gun's Garage Dinner and Show

Tommy Gun's Garage Dinner and Show

Celebrate the 1920s in Chicago, an era of gangsters, jazz and flappers, during this dinner performance of Tommy Gun’s Garage in the Windy City. This lively, fun-filled show, complete with plenty of crowd interaction, is a sure-fire crowd pleaser.

Choose an evening performance time for your show that fits your schedule. Then head to the theater, located through the “El” train tracks, feeling like you’ve reemerged in the 1920s. The venue is decked out head to toe in period-appropriate decorations, including silent movies, 1920s memorabilia, a replica wall from the infamous St. Valentines Day Massacre, pictures of gangsters and cops and a 1928 Ford Model A.

Start your night watching the show’s cast of “Molls” and “Mugs” dance and sing along to famous period performers like Duke Ellington, Fats Waller, Cole Porter and George Gershwin, all accompanied by music from Chicago’s own Sinfully Orchestra. 

As you watch, tuck into a meal of steak, pasta, chicken or fish (see menu in the Itinerary below). Then follow along with “Gloves” and “Vito” for a comedy show that’s sure to delight, complete with lots of song, dance and audience participation. 

All of a sudden, your performance will be “raided” by the cops, accompanied by the appropriate sirens and flashing lights. You might even get called up on stage for a hilarious “sobriety test,” administered by Officer Murphy, and get “interviewed” by Vito. 

Valentine’s Day WeekendGuests you visit Tommy Gun’s Garage during Valentine’s weekend will enjoy a special historical re-enactment of the infamous 1929 St. Valentine’s Day Massacre, a grisly mob killing carried out as part of a larger war between the rival Italian syndicate of Al Capone and the Irish mobsters of Bugs Moran.


Customer Reviews


5 star rating: Highly Recommended December 2016

Fantastic city and wonderful people. So much to see and do. Travelled on cta which was great value for money. Lincoln zoo is a must especially with the Christmas lights. Chicago trolley and bus tour is packed with information and the drivers are great.
Tommy guns restaurant/show was tremendous fun and a great venue for celebrating my son's 21st birthday.
Chicago is not to be missed and we will definitely be returning.


5 star rating: Highly Recommended October 2016

The show was great - would recommend it!

peter s

5 star rating: Highly Recommended October 2016

Enjoyed the food,the show was well done and the staff excellent


5 star rating: Highly Recommended September 2016

What a great show! We really enjoyed ourselves! The food is super good as well as the service! I've already told many friends to check it out!

Philip S

5 star rating: Highly Recommended September 2016

Good entertainment. Food a bit basic as per all these where the staff do the show and waiting on tables. A good night had by all.

Peter T

5 star rating: Highly Recommended August 2016

Great fun and entertainment! Servers are your entertainers and they are all very good. Lots of singing, dancing and comedy. Opportunity for a photo shoot and plenty audience participation. Food and cocktails great too!

Amy S

5 star rating: Highly Recommended August 2016

Very Fun!

Diane S

5 star rating: Highly Recommended August 2016

Well worth the visit. Mobsters and flappers interacted with the audience. Exceptionally funny performance.


5 star rating: Highly Recommended August 2016

We were not sure what to expect, but were pleasantly pleased with our decision to attend the Tommy Gun's Garage Dinner and Show. The cast and staff were very talented and entertaining. We definitely recommend.

Corycat Canada

5 star rating: Highly Recommended 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

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