Old Chicago Gangster Bicycle Tour

Bobby's Chicago Bike Hike

What You'll Get

Meet your guide and get outfitted with safety gear and a bicycle. From there, pedal off to learn about Chicago’s mobster history. Your expert guide leads you past the territories of Al Capone and other famous gangsters who ruled territories of Chicago’s South Side during the Prohibition era.

Along the 13-mile (21-km) route, cycle past former mob homes and hangouts that were popular with gangsters in the early 20th century. Many of the homes you see belonged to members of the Chicago Outfit, a crime syndicate that was once the biggest criminal organization in the Midwestern United States.

Your tour takes you other sites related to the mob, such as Chinatown, Bridgeport, the old Levee District, which was once a red-light district. Stop at Palmisano Park, an innovative park that was built on the site of an old rock quarry and former dump. Even this lovely green space has a scandalous story that was exposed by reporters from the Chicago Sun Times in 2004.

Your tour isn't all about crime. It also take you to scenic sites such as the Prairie Avenue District, which became a fashionable residential district after the 1871 Great Chicago Fire and is on the National Register of Historic Places. Bike along lakeshore paths that afford great views of Lake Michigan, and glide past McCormick Place and Museum Campus. You'll even enjoy classic Italian beef sandwiches at a Chicago original hangout. 

Expect to ride about 13 miles on a route considered moderate to advanced, with plenty of stops to rest and listen to your guide’s informative commentary. Your tour ends after about three hours when you return to your starting point.

Additional Information

  • Confirmation will be received at time of booking
  • This tour is appropriate for all ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided. Child bikes, seats and tagalongs are available.
  • Please note: children and adults must be strong, capable riders and be able to bike for 13 miles
  • 4-hour guided bicycle tour
  • Bicycle and helmet
  • Sample of Chicago's world-famous beef sandwich

  • Gratuity (optional)
  • Food and drinks

Departure Point
Lake Shore Drive

Departure Time

4 hours

Return Details
Returns to original departure point

Voucher Info
You can present either a paper or an electronic voucher for this activity.

The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Bobby's Chicago Bike Hike in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.

This offer is not eligible for promo codes.

The Fine Print

ALL SALES FINAL. Voucher valid only for date and time listed; may not be exchanged or redeemed for other dates. Purchaser name and phone number must be provided at checkout; this information will be shared with Viator and the tour operator for purposes of order fulfillment. Groupon promo codes may not be used for this offer. Groupon voucher Terms of Sale and Extraordinary Event Policy do not apply. See Viator voucher terms under "Viator Vouchers" here. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts.

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