Old Chicago Gangster Tour by Bike

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.