Tours/Chicago/Chicago's Original Gangster Tour by Bus
Viator · group up to 10 pax

Chicago's Original Gangster Tour by Bus

4.6(150)Chicago1 hour
VIATOR4.5(71)TRIPADVISOR4.8(79)

Description

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it. Reservations are strongly recommended.

Tour Options

Untouchable Tour

Itinerary

Pass by

See the site where John Dillinger was killed.

10 min

See the famous cathedral where Dean O'Banion used to be a choir boy as a child. As an adult, his North Side Gang, owned a flower shop across the street named Schofield's which handled all of the flowers for the mob funerals. In 1924, O'Banion was killed in his flower shop.

Highlights

Raffles and Prizes

What's included

Included
Raffles and Prizes

Traveller Ratings

4.6
150 reviews
5
126
4
10
3
6
2
1
1
7

Important Information

  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

Reviews(150)

N
Navigator822911
July 3, 2026
Worth it.

Second time taking this tour over the last ten years. Last time we had our young adult sons with us, this time just me and my husband. Heard a lot more of the history, liked the pamphlet and photos to follow along with the mobsters history. Comfortable seats, sound was good, host was funny, and informative.

L
Leo_F
July 3, 2026
Don't book this tour they charged us even though we didn't get to go because they left us.

Charged for the tour but didn't even get to go. They left us at the curb waiting to go and called ahead too but they still left.

S
simonaH4712BA
July 2, 2026
Fun, but a little dicey on the truth

I’m a little disappointed in the level of research… several of the points made were incorrectly oversensationalized. However, my tour guide was awesome, and ‘ fairly sure had nothing to do with the less accurate aspects. She had great comedic timing, was so sweet and absolutely deserves praise. Big shout out to Marie Genko of the Genko pure olive oil company!

G
Guide769515
July 2, 2026
Very enjoyable informative experience

Very friendly driver and host. Funny and informative. Really enjoyed the experience and a plus my husband won a mug! 😁

P
Pauline_D
June 30, 2026
Cancelled before we started!

Sun 28th was a hot morning. We walked 45 min to get to start point. On arrival the agent said there was a problem with AC and the bus would be 5 min late. Anyway it went from 5-35 min before he told us he was cancelling the trip. Not a good service. There were at least 18 people let down. All payments were made and now we have to wait to get refunded.

Operator response

Hi Pauline, Sunday was indeed a hot day. We pride ourselves on providing an entertaining and comfortable tour for our patrons. Unfortunately, that morning there was a mechanical failure on the bus. The delay in repairing the AC took longer than the garage initially estimated. Ultimately we decided to cancel the 11am tour, as we did not feel right charging folks for a tour that would have to be shortened. Our guide on the scene explained this, and offered to transfer anyone that could to the 1pm tour that day at no charge. Most patrons were able to, and had a great time. We are sorry it didn’t work out for you this trip. As soon as you indicated you would not be able to transfer, we processed your reservation for a refund. We hope the next time you visit Chicago you’ll look us up, and give us the opportunity to show you a swell time. Cheers, Trixie

W
W8078SRtracyw
June 27, 2026
So entertaining!

Our female tour guide was amazing and so entertaining! We’ve been to Chicago a few times and this is hand down, our favorite tour!

T
Todd_M
June 22, 2026
Chicago tour

Travel was very smooth, driver was excellent. Info was good. Enjoyed the music and learning more about Chicago

C
clairetI9070NP
June 19, 2026
Great Gangster Tour!!

Shoutout to Two- Gap Johnny for being a fabulous guide and entertainer. It was fun learning about the history of the dark underbelly of Chicago during Prohibition. Definitely recommend a tour with them!

V
victoriahT9593DL
June 18, 2026
Gangster bus show

This was the highlight of my experience with this trip. Nelson was out "gangster guide." He was very knowledgeable and funny. He worked his audience and could ad lib very quickly. I love theater and this was the best. Yes Nelson sent me. He get 10 stars from me. I know they only get 5 for a great show but he deserves more! Thanks Nelson for a great show!

K
Karen_M
June 17, 2026
Great Guides

Great guides who are very knowledgeable and dress in costume. There is a lot to see on the tour, however, you don't stop to get off the bus for pictures. The bus does pulls over for a narrative of the location.

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