Old Chicago Gangster Electric Bike Tour
Bobby’s Bike Hike is rolling out the best Chicago mafia tour every weekend of the summer! This electric 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 e-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 motorized function of our fleet of e-bikes makes riding a breeze! Relax and buzz through town, focusing on the incredible sights and awe-inspiring history this guided adventure has to offer!
See Chicago Like You’ve Never Imagined on Our Mafia Tour
Perhaps you live in Chicago and you consider yourself well-versed in the city’s history and its people. Or maybe you are visiting the city and you know only what you have read in books about The Windy City. No matter how much or how little you think you know about Chicago, you will learn loads more on one of our gangster tours.
You will discover people and places that will thrill you as you move past on your e-bike. You will encounter surprises and learn about things you may not have known about in Chicago history. These are the types of stories that make history come alive! The gangsters who once terrorized law enforcement had a complex relationship with others in the town. People had mixed feelings about their presence, enjoying the benefits of doing business with them but living in fear of the lawlessness they encouraged.
In Chicago, the public’s relationship with the mob was complicated, to say the least. Does that sound intriguing? Here are some other reasons you should consider taking our fascinating gangster tour in Chicago:
- It’s better than a textbook: You can read about these locations, but to truly appreciate the stories behind them, you have to see them.
- It’s interactive: You can ask your tour guide questions along the way and engage with your fellow bikers as you hit the different stops. You may find you delve into even deeper issues than you expected on this tour.
- It’s a tour with depth: On other tours, you glide past historic sites while the guide reads pre-written explanations. On our tour, you can get out and explore the nooks and crannies of Old Chicago on your own two feet.
We begin the story in the River North neighborhood. A stop at the Chicago River reveals the important ways that geography contributed to the city’s rapid growth in the 19th century and the corresponding rise of its criminal underclass. A few blocks away lies Holy Name Cathedral, seat of the Archdiocese of Chicago — and location of a notorious mob hit. After Holy Name, we’ll visit a riverfront plaza with panoramic views of the Loop’s architectural treasures, including the Jeweler’s Building, a favorite Al Capone hangout.
Next, you’ll enjoy a beautiful ride south to Museum Campus via the Chicago Riverwalk and the Lakefront Trail. With the Shedd Aquarium and the Field Museum as our backdrop, you’ll learn how the Outfit became dramatically richer and more powerful in the 1930s and 40s through its exploitation of labor unions. The tour then gets up close and personal with Soldier Field before riding west through Prairie Avenue, Chicago’s wealthiest neighborhood in the late 19th century, and through what was once the Levee, Chicago’s notorious red-light district from the same era.
After riding along the main thoroughfare of Chicago’s bustling Chinatown and learning about the reign of Sam Giancana during the 1950s and 60s, it’s time for a well deserved lunch break in the blue-collar neighborhood of Bridgeport. Enjoy your choice of an Italian beef or eggplant parmesan sandwich, compliments of Bobby’s Bike Hike.
From Bridgeport, it’s time to head back to Bobby’s HQ. We get there by riding east through Bronzeville along streets that Jim Croce once sang were “the baddest part of town” (but have since become perfectly safe) all the way to Lake Michigan. After a pause to catch our breath and admire the views, the final leg of our journey takes us on a gorgeous, unhurried ride along the lake past McCormick Place, Northerly Island, and Grant Park until we arrive at Bobby’s safe and sound. By the end of this tour, you’ll see why Bobby’s Bike Hike is the best Chicago gangster tour around.
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.
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