South Side Gangster Bike Tour

From: $64   


South Side - Chicago, IL


April through October:
Saturdays - 9:30 AM

*Select Wednesday, Friday, and Sundays are added in peak season

Discover the historic, scenic and seedier side of Chicago on the South Side Gangster Bike Tour!
  • Winners of a Trip Advisor's 2013 & 2014 Certificate of Excellence, the tour guides will lead you through various areas of Chicago's historic South Side
  • Explore famous mobster hangouts and homes, Al Capone's old stomping grounds, the Red Light District and the Lakefront
  • Taste a sample of Chicago's world-famous Italian Beef Sandwich
  • Jump on the biking bandwagon and see Chicago's sights in a fun, unique way!

More detailed description >


Explore the historic, seedy side of Chicago on the South Side Gangster Bike Tour! And don't worry, you won't be sleepin' with the fishes at the end of it!

On the guided 4-hour tour, visit the old stomping grounds of Al Capone and other illustrious mobster hangouts that made the South Side of Chicago famous.

Up-close highlights of the 12 mile, moderate ride may include:

  • Bridgeport
  • The McCormick Place
  • Chinatown
  • The hidden Palmisano Park
  • Italian hangouts of the past
  • Chicago's Red Light District
  • Museum Campus
  • The Lakefront
Join Chicago's outfit by jump-starting your day with this guided tour of the notorious South Side!

Key Info >

Essential Information:

  • Cruiser bikes and helmets are provided
  • Each bike is equipped with front pouches and back racks for storage of smaller items
  • Tour covers approximately 12 miles in 4 hours

4 hours

Maximum Participants:
This bike tour will be enjoyed by up to 20 people.

Only booked participants may go on the tour.

Weather Dependent:
This experience is not weather dependent. If it happens to rain, rain gear will be provided.

What to Wear:
Casual attire and footwear that is comfortable for biking.

Booking Information:
For this South Side Gangster Bike Tour experience, it is recommended to request bookings at least 14 days in advance.

Cancellation Policy:
Prior to scheduling a date and confirming a booking for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have received a booking confirmation, cancellations and rescheduling are allowed up to 5 days prior to the experience. Failure to appear on your booked date or to cancel and reschedule at least 5 days prior to your booked date will result in the loss of the value of your experience.

Experience ID:

View FAQ's >

  1. What are the bikes like?
    All bikes are deluxe comfort bikes with fat tires, cushioned seats and fenders to keep you clean. Each bike is equipped with front pouches and back racks for storage of smaller items.
  2. How long and strenuous is the tour?
    The South Side Gangster Bike Tour is a moderate, 12 to 13 mile bike ride lasting approximately 4 hours.
  3. Are there any age restrictions?
    This tour is not recommended for children under the age of 12.
  4. What if it rains?
    The South Side Gangster Bike Tour operates rain or shine. Rain gear will be provided if needed.
  5. Is water included on the bike tour?
    Water is not included on the tour, but is for sale at the meeting location. We recommend bringing your own water bottle if you have one!

Customer Reviews:

  • South Side Gangster Bike Tour

  • August 25, 2016

  • 5

  • Chicago

"I had the best time on the tour. William (our guide) is the best and has considerable knowledge. He especially made me feel safe in traffic which I sometimes feel nervous about while bike riding. Thanks again, I would highly recommend this experience."