• Location: Chicago, Illinois
  • Duration: 4 hours (approx.)
From USD $ 63.85 View price calendar

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Cycle through Chicago's Southside neighborhoods, the historic epicenter of mob activity, on this 4-hour bike tour. Learn about the history of the Chicago Outfit from your cycling tour guide and visit important sites in Chicago's gangster past like Al Capone's favorite hangouts, the red light district and other mob landmarks. Pedal through Palmisano Park, Bridgeport and Chinatown, then explore the scenic bike paths on the city's Lakeshore. The 13-mile (21-km) route is moderately difficult and suitable for those with some cycling experience; all necessary equipment is provided.


  • 4-hour guided bicycle tour of Chicago’s Southside neighborhood
  • Cycle past the former haunts of Al Capone and other infamous Chicago mobsters from the early 1900s
  • Learn from your knowledgeable guide about the history of the Chicago Outfit on the Southside
  • Wheel through Bridgeport, Chinatown, Palmisano Park and the former red-light district
  • Bike by former mobsters' homes, Museum Campus, McCormick Place and the historic Prairie Avenue District
  • Take this moderate bike ride for a great perspective on Chicago in the 20th century

What You Can Expect

Old Chicago Gangster Electric Bike Tour

Bicycle Tour

Make your way to the prearranged meeting point to meet your guide and tour group. Listen to a safety briefing and get outfitted with a bicycle and safety gear before setting out on your 13-mile (21-km) route is moderately difficult and suitable for those with some longer-distance cycling experience.

Cycle past former mob homes and hangouts that were popular with gangsters in the early 20th century. Many of the homes belonged to members of the Chicago Outfit, a crime syndicate that was once the biggest criminal organization in the Midwestern United States.

Visit the Prairie Avenue District, which became a trendy residential neighborhood after the 1871 Great Chicago Fire and is on the National Register of Historic Places. Bike along lakeshore paths, past the Museum Campus and McCormick Place, for views of Lake Michigan. You'll even enjoy classic Italian beef sandwiches at a Chicago original hangout. 

Coast through Chinatown, Bridgeport and the old Levee District, which was once a red-light district. Stop at Palmisano Park, built on the site of an old rock quarry, and in possession of a scandalous history.

After approximately 4 hours, return to your starting point.

Customer Reviews

Steffen M

5 star rating: Highly Recommended July 2016

Great tour!

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