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  • Languages Offered: English
Itinerary
Your tour meets in Chicago’s Near North Side, across from the Water Tower Place shopping mall. Hop aboard an air-conditioned coach bus, and get ready to learn about the city’s shady past.

Your driver provides a smooth ride through the city, bypassing traffic when possible, while your guide points out main landmarks that play a part in the area’s gangster history. Hear stories about big-time mobsters—including Al Capone, Tommy O’Conner, Bugs Moran, and Hymie Weiss—as well as The Untouchables, who helped bring them down.

You’ll see locations where well-known crimes happened and the courthouses where the bad guys were tried for their crimes. Some parts of this tour allow you to get off and wander around important attractions on foot.

Your tour ends with a drop-off at the departure point.
Locations visited
The Loop
The Magnificent Mile
Lincoln Park
See all 6 locations
Overview
Chicago has a past filled with big gangster names such as John Dillinger and the infamous Al Capone. Dive deep into the city’s mobster ways with a guide who knows where “the business” was done. Stay comfortable during this bus tour, which is perfect for any type of weather, and choose from multiple departure times to best suit your schedule.
Highlights
  • Guarantee your spot on this tour by booking ahead—perfect for big groups
  • Learn about Chicago’s mobster past from your guide 
  • Multiple departure times available to fit your busy sightseeing schedule 
  • Charge your cell phone on the go with outlets on the bus
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LanguageEnglish
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Show reviews that mention
All reviewsjohn dillingercool thingsour tour guidethe buscome alivebooked this tourenjoyable tourthree timesinteresting factsgreat guidehistory lessonlots of funsmall groupthe magnificent milecaponebenbasement
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1 - 5 of 112 reviews
Reviewed 2 days ago
Very Fun!

My girlfriend booked this as an activity and I was skeptical at first, but it ended up being very fun and informative. Our tour guide was great (dont remember his name) and him being a Chicago native and history guy, he was really able to...More

Thank JP L
Reviewed 6 days ago
Ben was very informative

Learn about people and place in Chicago we never knew. Ben was our tour guide and he did a wonderful job. We would recommend to anyone going to Chicago. I have been going to Chicago many years ( over 25 +) shopping, this was my...More

1  Thank Donna E
Reviewed 1 week ago
Ben is

Fun and informative. Ben was our tour guide and did a FANTASTIC job. BOTH my husband and I enjoyed the tour and would recommend it! Try and book with BEN to ensure a great time. (I think these types of tours are heavily dependent on...More

Thank rrrandi
Reviewed 1 week ago
Fun and Informative

I was pleasantly surprised by this tour. Another review said it was mostly about Chicago crime rather than mobsters, but I found it to be the exact opposite. A little more about famous and influential mobsters rather than random crimes. And even so, the crimes...More

1  Thank TyrisFlare
Reviewed 1 week ago
Fair at Best

Took this tour a week ago with Stanley O as our guide. First of all, I thought we should all have had audio pieces so we could hear him when we got off the bus. At our first stop, where Dillinger was murdered, we had...More

3  Thank Travelor758
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Questions & Answers
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winter2016a
6 August 2018|
AnswerShow all 2 answers
Response from wendygalasso | Reviewed this property |
I used park whiz app and parked at a hotel with valet very nearby
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winter2016a
6 August 2018|
AnswerShow all 6 answers
Response from John S | Reviewed this property |
If you are staying at a hotel close to downtown or the theater district, a cab is less than $10. We didn't rent a car, or drive to Chicago.
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Yayayayayayaya
14 May 2018|
Answer
Response from wendygalasso | Reviewed this property |
1-1/2 to 2 hours, departs severssl times a day
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