Southside Chicago Outfit Bike Tour

  • Free cancellation *
  • No booking or credit card fees
  • Instant confirmation Confirmation is instant if you book 1 days before your tour
Al Capone smiles in a mugshot
Southside Chicago Outfit Bike Tour - Picture 1
Al Capone smiles in a mugshot
Southside Chicago Outfit Bike Tour - Picture 4
Southside Chicago Outfit Bike Tour - Picture 5

What To Expect

Chicago's seedier side will be unveiled on this ride through the Southside's most notorious areas, including the old Bridgeport neighborhood.


Bike Tours around Chicago
Departs From:
Meeting Point:
540 N. Lake Shore Drive Chicago
4 hours
Product Code:
Voucher info:
Print voucher. You will not have access to the tour without this voucher.
Featured On:
Chicago City Tours & SightseeingChicago Hiking, Cycling & Outdoor ActivitiesCity Tours & SightseeingHiking, Cycling & Outdoor Activities


Learn about the history of the Chicago Outfit as we roll by famous mob hangouts and homes, Chicago's old red-light district, and Al Capone's old stomping grounds. This tour will explain the history of the outfit and how it has transformed over the years into what it is today. And enjoy a sample of Chicago's world-famous Italian beef sandwich during the tour!


  • Bridgeport

  • Chinatown

  • Hidden Palmisano Park

  • Old Italian Outfit hangouts

  • The Old Levee District (Chicago's Red Light district)

  • The McCormick Place

  • Prairie Ave District

  • Museum Campus

  • Lakefront


  • Guided bike tour

  • Bike rental

  • Helmet

  • Sample of Chicago's world-famous Italian beef sandwich


  • Meals and drinks

  • Personal expenses

  • Tips and gratuities

  • Optional activity costs

Please Note

  • The level for this tour is moderate to advanced, a participant must be able to ride a bike for 13 miles (environ 20 km).

  • Children 3 and under will be charged a 5USD ticket price which goes toward reserving their special equipment. Please let us know how many infants/young children will be attending and mark any needed special equipment (child seats, trailers, tag-a-longs) when you book.

  • Please wear comfortable clothing and shoes.

  • In case you are interested, you may bring a camera and enter your best picture in our Photo Contest.

  • You are suggested to give your guide a 10% to 20% gratuity.

  • Our tours will run even during rainy days.

Cancellation Policy

  • Free cancellation: 8 days or more prior to start date of activity.
  • 20% Cancellation Fee (80% reimbursement): between 4 to 7 days prior to date of activity.
  • 100% Cancellation Fee (no reimbursement): 3 days or less prior to date of activity.

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