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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


5 star rating: Highly Recommended November 2016

very good trip and very well informed tour guide i will say that this is informative tour.


5 star rating: Highly Recommended November 2016

Fun and full of interesting facts!


5 star rating: Highly Recommended November 2016

Great tour - fun and informative.


5 star rating: Highly Recommended November 2016

We had so much fun on this tour! John was fantastic!!!! So much energy and knowledge. I learned so much and was never bored. It was so cool seeing all of these famous spots in person. I highly recommend this experience!

oleksandra d

5 star rating: Highly Recommended November 2016

Ben was an amazing guide! Intresting and totally different from all other tours in a good way!Have fun on your tour with Ben!


5 star rating: Highly Recommended October 2016

Definitely worth the time and money. I wish this tour would have lasted longer. There is so much history!

April B

5 star rating: Highly Recommended October 2016

The tour guide was great. He was informed and energetic about the tour information. The driver was helpful and calm in heavy traffic. This was one of the best things we did while visiting Chicago.

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

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