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Old Chicago Gangster Bike Tour

Bobby’s Bike Hike is rolling out the best Chicago mafia tour every weekend of the summer! This bicycle tour of Old Chicago will introduce you to the crazy and colorful people and places of Chicago’s bygone gangster days.

Our Old Chicago Gangster bike tour goes on a journey through time to an era when Chicago was ruled from behind the scenes by a shadowy criminal cabal known as the Chicago Outfit. You’ll learn about the dramatic rise and the often grisly demise of men such as Jim Colosimo, Johnny Torrio, Curly Humphries, Joe Accardo, and of course, Al Capone, all while taking in Chicago’s present-day splendor.

The easy function of our fleet of comfort bikes makes riding a breeze, but feel free to upgrade to our electric bike option for an optimal ride! Relax and buzz through town, focusing on the incredible sights and awe-inspiring history this guided adventure has to offer!  16 years and older only.  Must be 16 years or older to operate an E-bike.

George Explains Our Southside Gangster Tour – Inspired by Capone

Here's one of our guides George explaining our newest tour. Check out our Southside Gangster Tour today! http://bobbysbikehike.com/Tours.aspx

Posted by Bobby's Bike Hike – Chicago Tours on Friday, June 7, 2013

What To Expect

Holy Name Cathedral is a historic church in the River North neighborhood and seat of the Archdiocese of Chicago. It’s also the site of a notorious mob hit from Chicago’s gangster days.

River North has been a epicenter of Chicago’s drinking scene since the city’s founding, and was a hub for Irish mafia bootleggers during the Prohibition era.
The newly redesigned Chicago Riverwalk is a stunning feat of recreational architecture, framing the legendary Chicago River, a classic route of transportation for the Chicago Outfit.

Slow-roasted and covered in giardiniera, the Italian Beef Sandwich has been a staple of the Chicago diet since our meatpacking heyday.

Museum Campus is a unique piece of waterfront parkland located just south of the Chicago Loop, and was the site of the 1933 World’s Fair, an event largely run by the mafia.

Built in 1924, Soldier Field is the oldest NFL stadium in the United States, and is an iconic landmark connecting the north and south sides of the city.

Prairie Avenue District is a South Side historic district and was home to some of the most fashionable residences built after the Great Chicago Fire.

Chinatown is a South Side enclave of Chinese American settlers who have been staunch allies of the Italian gangsters since their arrival in the city.

Bridgeport was the modest South Side home of countless Chicago Outfit members in the mid-20th century. Today, it ranks as one of the city’s most diverse neighborhoods and still home to many local political families.

Since the early 20th century, Bronzeville has been one of the most significant African American communities in America and remains an epicenter of Black culture.

Our Vendors

Ricobene’s has been a Chicago institution since the 1950s, serving up some of the finest italian beef sandwiches, hot dogs, and pizza in the city.

Book Your Gangster Tour in Chicago Today

We can tell you lots of reasons why you should book a tour with us, such as:

  • Our expert guides
  • Our strong connections that allow us access to locations other tours don’t provide
  • Our superlative safety record

But the bottom line is this: You should take our tour of Old Chicago because it’s fun!

You will have a blast e-biking all over town with your group. It’s a fantastic activity for people of all ages and fitness levels. You won’t find a lot of things to do around town that are this inclusive. You will also love how engaged and enthusiastic our tour groups are. We think this is a great way to see and experience the city, and our guests tend to agree. That’s why we’ve been rated the No. 1 tour company in Chicago for 10 years running by Trip Advisor.

Reserve your spot on our Chicago Mafia tour today, and get ready for the fun to begin.

What Our Customers Are Saying“We had an excellent guide for our Gangster tour. After demonstrating necessary safety protocol, we rode through the city taking periodic stops along the way to hear interesting facts about the city and gangster life. Bobby’s Bike Hike treated us to an incredible sandwich for lunch – great ride, great tour, fantastic guide!”

– Jonathan H.  Amsterdam, Netherlands

Old Chicago Gangster Bike Tour

Duration: 4 hours
Length: 16mi/26km
Level: Moderate/Intermediate
Schedule: Private Groups Only
Age: 16+

(includes Bike)

Price: Fri-Sun Mon-Thurs
Adults $55.99 $55.99
Youth (Ages: 4-11) $39.99 $39.99
Infants (Ages: 0-3) $9.99 $9.99
Electric Bike Upgrade $19.99

Reserve Now
Private Tour