Insider's Guide to Chicago

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Tour code: 6138CCT

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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

Kieran C

5 star rating: Highly Recommended May 2016

I would recommend - tour guide was good fun and informative.

Gary Y

5 star rating: Highly Recommended May 2016

A very interesting tour. Although it seemed much too short we enjoyed it very much. There must be a longer tour available with the amount of crime that Chicago has the reputation for. By and large, the driver and tour guide were most excellent.

Thomas J T

5 star rating: Highly Recommended April 2016

Jade was our tour guide. He was great. The stories were colorful,exciting and intriguing. I liked the fact that we were able to get off the bus and visit the actual sights. Chicago is a great city to visit and I would highly recommend your tour. Your service was easy to navigate, we will use it in the future.


5 star rating: Highly Recommended March 2016

Tour guide was funny and engaging. She also gave many random facts about Chicago.

Sheryl A. S

5 star rating: Highly Recommended February 2016

Our guide was AMAZING!

Matti F

5 star rating: Highly Recommended January 2016

Excellent tour - even for a cold Chicago day! :-

Never knew that there were so many mobsters and criminals in Chicago - and the tour guide made it fascinating!

Daniel S United States of ... 

5 star rating: Highly Recommended January 2016

Fun and entertaining.

Rodney C

5 star rating: Highly Recommended December 2015

It was great. I am huge into the mobsters of the past

Patricia B

5 star rating: Highly Recommended November 2015

We have taken several diferent tours in Chicago. So when our visitors came to town this year, we decided to try something totally out of the box. This tour was a lot of fun! Our guide was not only informative but he had a great sense of humor. Our guests loved it and had a great time. I would highly recommend this tour to others.

Kc2Kctoo United States of ... 

5 star rating: Highly Recommended November 2015

Well informed guide and a great tour! Well worth the time and money.

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