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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for all fitness levels including beginners and families.
Wildlife
History
Chicago’s lakefront was designated a public parkland in the early 1900s, securing open space against urban development.
Conservation
The tour operator promotes responsible riding to minimize impact on park areas and wildlife habitats along the lakefront.
Bobby's Bike Hike
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.
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.
Bring a helmet
Wearing a helmet is important for safety on city streets with mixed traffic.
Start hydrated
Chicago’s lakefront can be windy; carry water to stay refreshed throughout the ride.
Watch for pedestrians
Stay alert in busy areas like Lincoln Park Zoo where foot traffic is heavy.
Use sunscreen
Open lakefront paths mean sun exposure, even on cloudy days—apply sunscreen before riding.
Comfortable cycling clothes
Light layers work well on cooler spring days while biking around the lake.
spring
Helmet
Protect your head during urban cycling.
Reusable water bottle
Stay hydrated in warm weather along the open lakefront paths.
summer
Sunglasses
Protect your eyes from sun glare reflecting off the water.
summer