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Explore Chicago's gangster past on this 1.5-hour mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, the Clark Street bridge, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites. 


  • Chicago crime tour by luxury air-conditioned coach
  • Explore Chicago’s most storied crime-related areas in the Gold Coast, Lincoln Park, Old Town, the Loop and Magnificent Mile
  • Hear stories about Chicago’s most notorious criminals and mobsters including Al Capone and John Dillinger
  • Witness the sites of history’s most infamous crime scenes including the St Valentine’s Day Massacre
  • Hop off to explore some places by foot with your guide

Why Our Insiders Chose This Tour

This unique tour takes you to the actual places where famous gangsters and mobsters carried out their evil and mischievous activities. You even get to explore a few of the places by foot, taking real steps into history!

Recent Photos of This Tour

What You Can Expect

Chicago Crime and Mob Tour

Chicago Crime Tour

Your tour will begin in Chicago’s Near North Side, across the street from Water Tower Place, where you will board your coach vehicle.  On board, an experienced guide narrates during your 1.5-hour tour of Chicago’s famed criminal and historical sights. Listen to thrilling stories of mobsters, violence and crime as your coach winds through Chicago’s historic River North, Gold Cost, Lincoln Park, Old Town, Loop and Magnificent Mile. Snap pictures and enjoy little-known tales of legendary mobsters Al Capone, ‘Terrible’ Tommy O’Conner, and Bugs Moran.  

Your mafia tour highlights Chicago’s most notorious crime scenes, including the courthouse where some of the most famed mob cases were tried, and the site of the grisly 1929 St. Valentine’s Day Massacre. Other notorious mob haunts you do a drive-by on are the Biograph Theater, Holy Name Cathedral, Clark Street Bridge, and Lake Street EL.  (Along the way, you can hop out of your ride for pictures.) When it's all over, you'll get a ride back to the Near North Side to end the tour.  

Customer Reviews

Natalie P

5 star rating: Highly Recommended October 2016

My friends and I had so much fun on this tour! Shelia was such a great story teller and we would have happily spent all day listening to the historical stories! We had so much fun that we returned to Harry Carey's after the tour for happy hour just to get more time to look at the old newspaper stories and artifacts! A must do!

Janis P

5 star rating: Highly Recommended October 2016

Love this tour and there is so much information. The highlight was going to Harry Cary and viewing all the old mob articles and pictures from Al Capone and Dillinger's days. We were in many parts of the city and I would have enjoyed some narration about DePaul and interesting places that we passed. The subject was kept primarily on crime but I would have enjoyed more information on different areas we passed! Overall a wonderful, funny, information packed 1 1/2 hours!


5 star rating: Highly Recommended October 2016

Our guide, Javier, was great


5 star rating: Highly Recommended October 2016

It was a lot of fun, the guide was excellent, he knew his stories and how to tell them in a very amusing way. It's something different to do, a trip into the past of the city.

Karen M

5 star rating: Highly Recommended September 2016

Tour guide was very knowledgeable and had a great sense of humor. Made it a lot of fun.

Rosalinda B

5 star rating: Highly Recommended September 2016

Loved, loved, loved this tour and the tour guide was very informative..would do again!!

Sandy U

5 star rating: Highly Recommended September 2016

Loads of fun. Tour guide Ben, was really funny, knowledgeable and entertaining. We saw parts of the seedier side of Chicago we never would have looked to find. My friends, some of whom were Chicago natives, learned things they didn't know. Bus was comfortable and it was nice to have someone else drive. Would love to take some of the other tours offered by this company. Good value for the money.

Liliana K

5 star rating: Highly Recommended September 2016

Very interesting experience!

Edward D

5 star rating: Highly Recommended September 2016

Allot of good information and history of crime in Chicago

Cheryl M

5 star rating: Highly Recommended September 2016

Our tour was one of the best! The guide was so knowledgable about the history of crime and the characters that he shared with us. The pace of the tour was enjoyable with stops where we exited to view important sights along the route. We would definitely recommend this trip to anyone interested in the history of Chicago.

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