Adventure Brief
Discover Chicago’s scenic Lakefront Trail with 2 Day Bike Rental. Convenient gear, safety tips, and easy access to miles of bike lanes await urban cyclists ready to roll.
2–6 hours
moderate
Family Friendly
No Experience Required
Discover Chicago’s scenic Lakefront Trail with 2 Day Bike Rental. Convenient gear, safety tips, and easy access to miles of bike lanes await urban cyclists ready to roll.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
2–6 hours
Fitness Level
Suitable for riders with moderate fitness who can handle city terrain and traffic conditions
Wildlife
History
Chicago's extensive lakefront trail system was developed in the 1930s as part of the city's effort to preserve public access to Lake Michigan.
Conservation
The city promotes bike riding as a green transportation alternative to reduce urban pollution and traffic congestion.
Bobby's Bike Hike
Discover Chicago’s scenic Lakefront Trail with 2 Day Bike Rental. Convenient gear, safety tips, and easy access to miles of bike lanes await urban cyclists ready to roll.
Bobby's Bike Hike is a Miami-based tour operator offering guided walking and bike experiences across Miami and bike rental services in Chicago. The company organizes neighborhood-focused food and culture walking tours in Wynwood, Little Havana, South Beach, and Miami Beach, plus bike-and-food adventures that highlight local cuisine and iconic city views.
In Miami, tours include the Wynwood Walls Food & Graffiti Art Walking Tour, Wynwood Walls Street Art Walking Tour, Little Havana Food & Culture Walking Tour, South Beach Food & Fun Walking Tour, and the Miami Beach Bikes, Bites & Views (Adults Only) bike and food tour. Several Miami tours run three hours, with options for VIP beverage add-ons like a Craft Drink package or a Mojito.
For Chicago, Bobby's Bike Hike provides multiple bike rental durations — half-day, full-day (same day return), and two-day rentals — plus guided routes such as the Chicago Family Food and Bike Tour and a highlights walking tour of top city attractions. Rentals come with complimentary maps, helmets, and locks.
All descriptions and trip options are based on published tour summaries. The operator emphasizes neighborhood-specific storytelling, local food stops, and practical support for riders and walkers alike, such as safety gear and route maps. This combination of guided tours and rental services makes Bobby's Bike Hike a practical choice for visitors seeking food-focused walks, street art tours, scenic bike rides, and flexible rental options.
Based In
Miami, FL
Headquartered in Miami
Tours Offered
11
Guided walks and bike experiences
Bike Rentals
Chicago & Miami
Half, full, and multi-day options
Audience
Family & Adults
Family-friendly and adults-only tours
Book Wynwood art walks, Little Havana food tours, South Beach strolls, or Chicago bike rentals — secure online reservations available.
Wear a Helmet at All Times
Helmets are provided but ensure you wear them securely for maximum safety on city streets.
Follow Chicago Bike Lane Rules
Obey all traffic signals and use designated bike lanes to stay safe among city vehicles.
Check Your Bike Before Heading Out
Use the complimentary locks and inspect brakes and tires before starting your ride.
Plan Your Route Using Provided Maps
Take advantage of the free maps to identify safe, scenic, and efficient paths throughout the city.
Helmet
Included with rentals to protect riders in an urban setting.
Lock
Provided to securely park your bike during stops.
Comfortable Clothing
Light, breathable attire makes city biking enjoyable in warm weather.
summer
Water Bottle
Stay hydrated while riding along sunny lakefront paths.
summer