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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

Hugo V

5 star rating: Highly Recommended July 2016

Excellent Tour

Katherine M

5 star rating: Highly Recommended July 2016

Very enjoyable!

Linus K

5 star rating: Highly Recommended July 2016

Very entertaining and interesting tour. Worth the time and money.

Patricia T

5 star rating: Highly Recommended July 2016

Excellent guide- Ben. Knowledgeable and entertaining.

Lois M O

5 star rating: Highly Recommended July 2016

My granddaughter, daughter, and I went on this tour. The facts were interesting, and the tour guide presented them in an entertaining manner. He was very knowledgeable. The stops made gave another perspective to the information we were getting. I would recommend this tour to anyone.


5 star rating: Highly Recommended July 2016

Wonderful tour! Bus was clean and cool, tour guide was funny and full of information - we had a great time! He gave us info about crime/mob but also some history on Chicago itself. He even recommended a few books and we've already started one, Devil in the White City - good book.

Sandra D D

5 star rating: Highly Recommended July 2016

The tour was fun and Informative!

Martha B

5 star rating: Highly Recommended July 2016

This tour was amazing!


5 star rating: Highly Recommended July 2016

Ben Archer was a very knowledgeable and entertaining tour guide.

Charisse E

5 star rating: Highly Recommended July 2016

This tour was amazing!

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