Famous "Outfit" Restaurant Hangout

Southside Gangster and Mafia Bike Tour

Product ID: 42854
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From £52.27 £41.82 per person

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Key Details
4 hours
Mobile Voucher Accepted
Printed Voucher Accepted
Instant Confirmation
Live Guide

Select date and participants:


What You'll Do
  • Roll by Chicago famous mob hangouts and homes
  • Learn about the notorious shoot out at Holy Name Cathedral
  • Ride through Chicago's former Red-Light District
  • Explore the Prairie Ave mansions
  • See Museum Campus sites
  • Enjoy leisurely ride along the lakefront bike path
  • Sample Chicago's world-famous Italian beef
Experience Chicago’s seedier side on this bike tour through Southside’s most notorious mobster areas and stomping grounds of famous Al Capone. Learn about the notorious shoot out at Holy Name Cathedral and ride through Chicago's former Red-Light District.
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. 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. You will also stop for a sample of Chicago's classic Italian beef sandwich.

Highlights include: 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 and the Lakefront.
What's Included
  • Bike tour with guide
  • Bicycle, helmet
  • Italian beef sample
What's Not Included
  • Gratuity
  • Food and drinks (water available for purchase at bike shop)
Cancellation Policy
Cancel up to 1 day in advance for a full refund
Meeting Point

Bobby’s Bike Hike World Headquarters 540 N. Lake Shore Drive Chicago, IL 60611 Entrance on Ohio St. just west of Lake Shore Dr. (Open in Google Maps)

Know Before You Go
Please note:
Wear comfortable clothing and shoes.
Tours run regardless of poor weather. Consider bringing a camera to capture the day's memories.

Level: Moderate
Length: 12mi/19km
Save up to 20%

From £52.27 £41.82 per person

Book now
Our promise to you
  • Speedy booking and reserved spots
  • No-hassle best price guarantee
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Bobby's Bike Hike-Chicago Tours & Rental

Product ID: 42854