Chicago Crime & Gangster Tour

Chicago Crime & Gangster Tour

Chicago Crime & Gangster Tour

Saturdays at 2pm – Reserve Today!

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-know and not-so-well-know Chicago Mob hangouts all while seeing the beautiful River North and Loop neighborhoods. And the best part – this Chicago Crime & Gangster tour is FREE!

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 were? Or where the infamous Florist Shop was located? Let our resident Crime and Gangster expert tour guide take you on walk through Chicago’s storied criminal past on this fun and educational walking tour through River North and Chicago’s Loop.

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.

You’re going to love this tour! Join today!

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

Crime Tour Meeting Spot

When: Saturdays at 2pm (Our Winter schedule starts on November 1 and runs thru April 1, 2017 – – Please check our Tour Calendar for the most up-to-date schedule)

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 – 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 you’re group is larger than 6 people and our times don’t work out contact us regarding a Private Chicago Walking Tour.

Chicago Loop Architecture Tour – This is our heaviest architecture tour and for good reason. Chicago’s Loop is loaded with incredible buildings and the people behind the designs are equally fascinating.

Chicago Total Loop Tour – This tour is for guests looking to get an all-around education on Chicago’s most-trafficked part of the city. We will touch on a little history, a little architecture and little bit of what the future of Chicago might look like.

Riverwalk & North Loop Tour – Is there a better way to spend a sunny day in Chicago than on the Chicago Riverwalk? We don’t think so. Our Riverwalk Tour begins where Chicago did an ends at the site of the world’s largest Tiffany Glass dome roof. You do not want to miss this one!

Michigan Avenue & Millennium Park Tour – Guests will not want to forge their camera on this tour as they will check off many to-do’s from their Chicago bucket list including: Wrigley Building, Chicago River, Carbide & Carbon Building, Wrigley Square, Crown Fountain, Cloud Gate & Buckingham Fountain.

Lincoln Park Neighborhood Tour – Take a break from the heavy tourist spots and take a stroll through one of Chicago’s most beautiful neighborhoods. See why there is a park named after the Wonderful Wizard of Oz and visit homes that survived The Great Chicago Fire of 1871.

Magnificent Mile Tour – Shop to you drop…AFTER this tour. We’re going to show and tell a different side of the Magnificent Mile than you’re used to. See the history (Original Water Tower) incredible buildings (John Hancock Center) and learn about the influential architects  (Meis van der Rohe) that shaped this part of Chicago.

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