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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

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.

Dave United Kingdom

5 star rating: Highly Recommended September 2016

I did like this tour as I am into mob history and am always reading a lot about so knew some of the facts that were given to us.

Betty T

5 star rating: Highly Recommended September 2016

Guide very humorous and informative. Thoroughly enjoyed the tour.

Harold E B

5 star rating: Highly Recommended September 2016

We enjoyed our tour very much. Our narrator did such a good job. Have used Viator tours before and were so pleased with how they conducted their tours and intend to use them in the future. Thank you Viator!

Jason Z

5 star rating: Highly Recommended September 2016

Very Informative and Fun Time, Had a great Time, Tour Guide was amazing

Freya G

5 star rating: Highly Recommended September 2016

I really enjoyed the history and the guide was extremely good.

William M

5 star rating: Highly Recommended September 2016

Very interesting tour and the tour guide knew his subject well and had a quite a nice sense of humour to go along with his tales.

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