easy
3 hours
Suitable for all fitness levels including beginners and families.
Ride through Chicago’s scenic lakefront and iconic neighborhoods on a top-rated 3-hour bike tour. Discover historic mansions, urban beaches, and local spots off the beaten path.
Starting at $49.99 | 3 Hours | Longest running, most popular family tour for 20 straight years!
Experience the best of Chicago on a 3-hour bike tour, rated top by Tripadvisor and USA Today. Explore hidden gems like the Gold Coast Mansions and Lincoln Park Zoo while cruising through charming neighborhoods and scenic beaches. Perfect for all ages, this adventure showcases how locals truly enjoy their city.
3 hours
This tour is what made Bobby famous, taking you off the tourist beat and onto the quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago, giving you a glimpse as to how Chicagoans enjoy their beautiful city. Highlights include the Gold Coast Mansions, Oprah’s House, the Playboy Mansion, Lincoln Park Zoo, Old Town Historic District, North Avenue Beach, and the Lakefront. All ages and fitness levels will enjoy, but children must be strong, capable riders!
Level: All ages and fitness levels, must be able to ride a bike for 9 miles.
Wearing a helmet is important for safety on city streets with mixed traffic.
Chicago’s lakefront can be windy; carry water to stay refreshed throughout the ride.
Stay alert in busy areas like Lincoln Park Zoo where foot traffic is heavy.
Open lakefront paths mean sun exposure, even on cloudy days—apply sunscreen before riding.
Chicago’s lakefront was designated a public parkland in the early 1900s, securing open space against urban development.
The tour operator promotes responsible riding to minimize impact on park areas and wildlife habitats along the lakefront.
Light layers work well on cooler spring days while biking around the lake.
spring specific
Protect your head during urban cycling.
Stay hydrated in warm weather along the open lakefront paths.
summer specific
Protect your eyes from sun glare reflecting off the water.
summer specific