Choose from Four Options
- $22.50 for a signature tour (up to $45 value)
- $27 for a Southside Gangster tour (up to $55 value)
- $39 for a Bikes, Bites, and Brews tour (up to $78 value)
- $22.50 for a full-day comfort hybrid-bike rental (up to $45 value)
Guides lead tours through the hotspots and history of Chicago. Signature tours, including the Lakefront Neighborhoods tour and the City Lights tour, cruise by such sights as Millennium Park and Oprah’s house, Buckingham Fountain and the Playboy Mansion, spending up to three hours at a gentle pace. The Southside Gangster tour lasts approximately three-and-a-half hours, spans 12 miles, and allows moderate riders to explore the seedy history of famous mob hangouts. As guides narrate, riders roll through Chicago’s old red-light district and pass by many buildings once frequented by Al Capone. The four-hour Bikes, Bites, and Brews tour includes samples of pizza, hot dogs, cupcakes, and beer—with veggie options available—spread across the lakefront. See the schedule here. Each tour includes bikes and helmets but not the guide gratuity.
Bobby's Bike Hike
Inspired by a love of fitness and a passion for travel and tourism kindled within him by his late father, Jeremy Lewno founded Bobby's Bike Hike to create an interactive Chicago biking experience. He named the company after his dad, Bob, an Arkansas bus-tour operator who taught him to focus on service quality over quantity. That advice has clearly paid off, as the business's guided tours have earned a number one ranking for activities to do in Chicago on TripAdvisor and the title of Best Organized Bike Ride from the Chicago Reader in 2010.
During the tours, which include rented bicycles, guides lead groups of about 20 riders past Chicago icons in Millennium Park and on the Museum Campus, or direct them to samples of pizza, hot dogs, cupcakes, and beer in and around Wrigleyville. The crew has designed a Tike Hike tour for kids 10 and younger, a historic Hyde Park tour that pedals past the home of President Barack Obama, and a mansion-studded lakefront tour, during which riders may glimpse Oprah waving or handing out complimentary helicopters at her main residence. Patrons can also rent Schwinn, GT, and Cannondale Comfort bikes, mountain, road, cruisers, and tandem bikes to explore the city on their own.