We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Tommy Gun's Garage Dinner and Show

  • 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
Tommy Gun's Garage Dinner and Show
From US$67.00
Check Availability
  • Overview
  • What to Expect
  • Important Information
  • Reviews
Select Date and Travelers
Saturday Dinner and ShowMost Popular
Dinner and show start at 6:00pm
From US$77.00
Friday Dinner and Show
Dinner and show start at 7:00pm
From US$72.00
Thursday Dinner and Show
Dinner and show start at 6:00pm
From US$67.00
Show 3 more
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.
What to Expect
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.
Reviews (158)
1 - 5 of 5 reviews
Reviewed 14 November 2018
Our show was a no show

My friend and I planned our trip to Chicago back in April. One of the first things we planned was Tommy Gun's as a friend had been before and said it was a good night and that we should go. We booked it for November...More

Date of experience: November 2018
7  Thank HillsDundee
Reviewed 15 October 2018
Staff were very welcoming.

My daughter and I had tried to book this venue for the weekend but were unable to get a table, consequently we ended up going on a thursday night, and I did get the feeling that it would have more of an atmosphere if there...More

Date of experience: October 2018
5  Thank lizm54
Reviewed 28 August 2018
Great dinner and entertainment

We had prime rib dinners that were delicious and tender. Service was speedy by costumed and fun staff. The show had great music and period costumes, very entertaining. The place was packed and yet the food was as ordered.

Date of experience: July 2018
1  Thank DJH65
Reviewed 7 August 2018
Very Entertaining

From the beginning to end, it was very good. They even got me on stage for a little fun. I brought my employees for a night out and they loved it.

Date of experience: March 2018
Thank Michael C
Reviewed 6 August 2018
Fun Time

The food was not so good, choose the lasagna. Seeing the smile on my 20 year old grandson's face the whole time the show was going on, was enough to let me know it was a hit! It was cute, but definitely could have been...More

Date of experience: June 2018
1  Thank OhLynne2
View more reviews
Travelers Also Viewed
Chicago Prohibition Tour
128 Reviews
from US$45.00*
Gangsters and Ghosts Tour in Chicago
65 Reviews
from US$27.00*
Chicago Crime and Mob Tour
547 Reviews
from US$39.95*
Chicago Night Crimes Tour
10 Reviews
from US$45.00*
Frequently bought together
Chicago Crime and Mob Tour
547 Reviews
from US$39.95*
Special Offer
Skydeck Chicago Admission
632 Reviews
from US$22.00*
Chicago Architecture River Cruise
3,330 Reviews
from US$41.44*
Special Offer
Chicago Explorer Pass
184 Reviews
from US$76.00*