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

Robert N

5 star rating: Highly Recommended June 2016

This tour was amazing!

Carolyn B

5 star rating: Highly Recommended June 2016

This tour was amazing!

Sonia M

5 star rating: Highly Recommended June 2016

Our host was great!!


5 star rating: Highly Recommended June 2016

Lots of tantalizing details about the Mob and Prohibition. A nice way to spend the afternoon.


5 star rating: Highly Recommended June 2016

This tour was amazing!


5 star rating: Highly Recommended June 2016

This is a great tour for those who want to learn a little about Chicago's shady past. Our tour guide Ben had lots of stories about the crime scene of the 20's and 30's. The air conditioned bus was especially nice for Chicago's hot and humid weather. I would highly recommend it to those who are history buffs.

Sharon D

5 star rating: Highly Recommended June 2016

loved it !!!


5 star rating: Highly Recommended May 2016

Do it it's really interesting and the guys who run the tour really make it fun and they know there stuff.


5 star rating: Highly Recommended May 2016

The tour was great fun and the guide was very knowledgeable.

Kieran C

5 star rating: Highly Recommended May 2016

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

Special Offer
$39.95 Save $4.00

From USD $ 35.95

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