Explore Chicago’s Iconic Sights and Flavors on a Family-Friendly Bike Tour
Difficulty
easy
Duration
4 hours
Fitness Level
Moderate fitness required; suitable for children strong enough to bike 9 miles comfortably
Overview
Pedal through Chicago’s top neighborhoods savoring iconic foods and sights on a family-friendly bike tour. Discover culinary history, city landmarks, and lakefront breezes on this accessible 9-mile urban ride.
Explore Chicago’s Iconic Sights and Flavors on a Family-Friendly Bike Tour
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Chicago’s cityscape unfolds beneath a wide sky, its gleaming skyscrapers meeting the restless waters of Lake Michigan. On this family-friendly bike tour with Bobby’s Bike Hike, you and your crew glide along flat, paved trails that thread through the city’s most storied neighborhoods — from the upscale Gold Coast to the lively Museum Campus. The city’s heartbeat pulses as you pedal beside the Chicago Riverwalk, beneath iconic architecture, and along the lakefront where waves lap the shore like a quiet dare.
Adventure Photos
Adventure Tips
Bring a reusable water bottle
Stay hydrated during your 9-mile ride especially on sunny days by carrying water with you.
Wear comfortable, closed-toe shoes
Supportive footwear helps manage flat urban trails and occasional pavement cracks.
Arrive early to secure bike and helmet fit
Getting checked in 15 minutes before the tour start ensures a smooth departure and proper gear setup.
Contact operator ahead for dietary needs
Email reservations@bobbysbikehike.com if you need vegetarian or allergy accommodations before booking.
Local Insights
Wildlife
- Common mallards near lakefront green spaces
- Urban squirrels darting through city parks
History
Navy Pier served as one of America’s largest pilot-training bases during WWI and WWII, before becoming a bustling entertainment spot.
Conservation
The tour promotes sustainable travel by encouraging biking over car trips and supporting local businesses along the route.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable bike shoes
Supports pedaling and protects feet on city streets.
summer specific
Helmet
Protects your head during the ride and is provided by the operator.
Light waterproof jacket
Useful in spring rain showers during the tour.
spring specific
Sunscreen
Protects your skin from sun exposure along the lakefront trail.
summer specific