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.