• Location: Chicago, Illinois
  • Duration: 3 hours (approx.)
From USD $ 67.00 View price calendar

Low Price Guarantee

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

Why Our Insiders Chose This Tour

What You Can Expect

Tommy Gun's Garage Dinner and Show

Tommy Gun's Garage

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.


Customer Reviews


5 star rating: Highly Recommended February 2018

Food was great, we had prime steak, really enjoyed the whole experience.

Ronald G

5 star rating: Highly Recommended December 2017

5 star rating all 8 in our party are still talking about the show and surprisingly the food was great too. When we go again we will go in period clothing to enhance the experience

Amélie B

5 star rating: Highly Recommended November 2017

I took my 17 year old cousin here during our recent trip to Chicago. We had a great evening, a lot of fun, food and drinks!
The staff is amazing, especially our waitress/singer/dancer Ruby :

Michael W

5 star rating: Highly Recommended October 2017

A must see and do when in Chicago. Great show and talented performers.


5 star rating: Highly Recommended October 2017

What a night. Fantastic food, great entertainment. I would definetly do this again if i am in Chicago.

Rick B

5 star rating: Highly Recommended October 2017

Lots of fun and a great meal. The whole cast was wonderful

Adrian M

5 star rating: Highly Recommended October 2017

Simply Awsome, fantastic night, would recomend everyone goes, it's really important to soak up the atmosphere and the mood, get involved and you will love it.


5 star rating: Highly Recommended August 2017

Although we were late getting there in our RV they were very surprized to find to old girls travelling in an RV so they treated us very well and really looked after us. Show was great and so was the food. Hope they read this review to see we ended doing roughly 12500 miles when we had to leave for home. Make sure you do this show you will enjoy it. Paula and Jocelyn from Australia. Thank you.

Roxanne S

5 star rating: Highly Recommended August 2017

The show was fantastic. A must see in Chicago. A great family experience. The performers were all very talented and fun. The dinner was excellent except for the prime rib. It was huge, but hard as a rock. Everyone's prime rib was over cooked. But the show was great.


5 star rating: Highly Recommended July 2017

We had 3 generations celebrating a 50th anniversary. Everyone had a great time! Our server/singer/dancer, Mona, could have doubled for Roseanne Barr. The food was very good and the interactive entertainment was a lot of fun. Parking is free and right next to the venue which is a real plus in Chicago. I woulfd recommend Tommy Gun's Garage to anyone who wants a fun filled evening.

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