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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

Juan Pablo B

5 star rating: Highly Recommended August 2016

It's a must go tour. Interesting stories never heard before!!!

Bo W

5 star rating: Highly Recommended August 2016

Great tour!


5 star rating: Highly Recommended August 2016

A must-do tour when in Chicago! Mitch and Sheila were the perfect guides. They were very knowledgable, energeticc and fun!

Charles A

5 star rating: Highly Recommended August 2016

Very interesting and entertaining!!!!

Charles A

5 star rating: Highly Recommended August 2016

Very interesting and entertaining!!!!

Thomas N

5 star rating: Highly Recommended August 2016

Jade and our driver made this a very entertaining trip for all of us, even the kids. My husband remarked, they sure know a lot about Chicago. That says it all. Very entertaining. Jade had the answers to all of our questions, had a great sense of humor. I would go again!

Aleta C

5 star rating: Highly Recommended August 2016

EXCELLENT FUN!! Our Tour guide, Mitch, was a fabulous fun, enthusiastic and knowledgeable guide. Enjoyed it very much.

Freda United States of ... 

5 star rating: Highly Recommended August 2016

We were in Chicago for my husbands birthday and looking on Viator for something fun to do. AAA referred this site to us, and we thought we would try it out in the US before we used it internationally. We saw this tour about Chicago crime and mobs and thought it would be great fun, it did not disappoint. Our tour guide, Jade, was a great storyteller funny and informative from beginning to end. Definitely worth the money if you enjoy the history of Chicago gangsters and gangs. We visited places where Al Capone, the Untouchables, Hymie Weiss and John Dillinger hung out. Some of the locations were the Holy Name Cathedral dont fall for the bullet hole trick, the Clark Street bridge and the site of the bloody St. Valentines Day Massacre. We were able to hop off many times for photo ops which was cool and Jade was great at answering all the mob questions as he had a lot of knowledge of all the subjects. We will use Viator again!!! And, have already recommended it. Thank you Viator!! Freda White

Lynn R

5 star rating: Highly Recommended August 2016

This was very interesting. We stopped at more places than I anticipated. I have lived in Chicago most of my life and I learned some things I never knew. It was a lot of fun!!

Hugo V

5 star rating: Highly Recommended July 2016

Excellent Tour

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