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Chicago Crime & Gangster Tour

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Intro

Free Chicago Walking Tours Chicago Crime & Gangster Tour takes you on an incredible journey through Chicago's storied past. You will learn how the Chicago Mafia came to power and visit some well-known and not-so-well-known Chicago Mob hangouts all while seeing the beautiful River North and Loop neighborhoods. And the best part - this Chicago Crime & Gangster tour is FREE!

The Characters

You have heard all of the household names before - Al Capone, Boss Dean O'Banion, George "Bugs" Moran, The North Side Gang & "Machine Gun" Jack McGurn. But do what the Beer Wars was? Or where the infamous Florist Shop was located? Let our resident Crime and Gangster expert tour guide take you on a walk through Chicago's storied criminal past on this fun and educational walking tour through River North and Chicago's Loop.

The Route

Starting at the picturesque Historic Old Water Tower at the corner of Chicago & Michigan Avenue our Chicago Crime & Gangster tour will clear the air on what really went down in Chicago during the roaring 20s and after.

Wind your way through the River North area learning about the multiple gangs and their leaders that were vying for a piece of the prohibition pie. Stops at Marina City Towers and the Lasalle Street Bridge will help explain how all of these characters crossed paths and shaped the future of Chicago.

And is there a more fitting end to the tour than Chicago's Federal Plaza - a place that represents law and order. The site of Al Capone's trial and conviction and now home to one of Chicago's most iconic pieces of public art - Calder's Flamingo.

Meeting Point: Old Water Tower - Corner of Chicago & Michigan Avenue. Google Maps

Distance: 2.1 miles walking distance

Time: 2 hours from start to finish

Cost: FREE! Our guides work off the generosity of our guests. If you felt your guide has done a good job you can show your appreciation at the end of the tour by leaving a tip.

What you will see: 

  • Old Chicago Water Tower
  • Holy Name Cathedral
  • Levi's Store - the former location
  • Marina Towers
  • Lassie Street Bridge
  • Chicago Crime Commission Headquarters
  • Federal Plaza

Stories you will be told: 

  • The start of gangs in Chicago
  • Boss Dean is shot at the Florist Shop
  • The Story of "Machine Gun" Jack McGurn
  • The Office gets bugged
  • How the business changed from bootlegging to loans & gambling
  • Peace talks break down
  • Al Capone's Trial & Conviction

More Free Chicago Walking Tours

We know you will love the Chicago Crime & Gangster tour, so why not plan ahead and book another tour? If your group is larger than 6 people contact us regarding a Private Chicago Walking Tour.