Chicago
My picks for Chicago bike tours range from lakefront rides to neighborhood food routes. The city is flat, and the car-free Lakefront Trail runs 18 miles along the water. Every tour here includes the bike and helmet.
Discover the ultimate foodie adventure in Chicago! Indulge in mouthwatering pizza, ice-cold beer, iconic hot dogs, and delectable cupcakes while exploring the city on a thrilling bike tour.
Most Popular★ 5.0“Lauren was fantastic! She was clear with her instructions and spoke in a fun manner about the attractions and stops. Enjoyed the evening ride and got a taste of the local deep dish pizza, Chicago dog, and IPAs. Relaxing and fun!”
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732 reviews4 hours 30 minutes (approx.)From $89.00by Bobby's Bike Hike - Chicago
Discover the charm of Chicago's lakefront neighborhoods on an exhilarating bike tour. Explore hidden gems, iconic sights, and soak in the vibrant atmosphere. Book your adventure today!
★ 5.0“Relaxed bike ride through so beautiful neighborhoods in Chicago. Local history a bonus! Liam, our guide was very knowledgeable.”
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241 reviews3 hours (approx.)From $59.00by Bobby's Bike Hike - Chicago
Discover the hidden gems of Chicago on our thrilling city bike tour. Get ready for an unforgettable adventure through the Windy City's iconic sights and vibrant neighborhoods.
★ 5.0“AJ was an awesome tour guide. It was a real fun day biking around the city of Chicago. I definitely recommend this tour for anyone who loves to bike and sightsee!”
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233 reviews3 hours (approx.)From $59.00by Bobby's Bike Hike - Chicago
Yearning for a taste of Chicago's vibrant culture and culinary scene?
★ 4.9“Excellent tour and way of seeing the city! Really enjoyable too!”
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141 reviews4.5 hoursFrom $89by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
Prepare for an unforgettable journey through Chicago's vibrant neighborhoods on the Lakefront Neighborhoods Bike Tour, where each stop promises a surprising twist.
★ 4.9“Great experience, my daughter was hesitant about a group ride, but was inspired by the tour to rent the Divvy Bikes for the rest of trip!”
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123 reviews3 hoursFrom $59by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
You'll be pedaling your way through Chicago's West Side, uncovering hidden culinary gems and indulging in the city's renowned foodie delights.
★ 5.0“We ran late and we're ever so grateful that they let us get our bikes and meet up with the tour guide at one of the stops. Tour guide was Great! The biking was a beautiful scenery. It was hard to hear the history from…”
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112 reviews4 hours (approx.)From $99.00by Bobby's Bike Hike - Chicago
Families can embark on a delightful journey through Chicago's vibrant cityscape, immersing themselves in the city's captivating sights, flavors, and cultural heritage.
★ 5.0“We took our grandsons, ages 11 and 13, on the Chicago City and Food Tour. There were 8 others who joined our group. Joe was our guide and was great with the kids! We saw a lot of sights and sampled Chicago style pizza, hot…”
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98 reviews4 hours (approx.)From $79.00by Bobby's Bike Hike - Chicago
Discover the Windy City like never before with our Chicago Full Day Bike Rental. Explore famous landmarks and hidden gems on two wheels. Book your adventure now!
★ 5.0“Consiglio vivamente di fare l’esperienza in bici lungo la pista ciclabile del lago. Un metodo per vedere tanto in poco tempo. Abbiamo sfruttato appieno la giornata, grazie alle bici. I nostri figli 14 e 12 anni felicissimi. Visitato tutti i parchi lungo il lago senza…”
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49 reviews1 day (approx.)From $29.99by Bobby's Bike Hike - Chicago
Uncover the unexpected on the Ultimate City Attractions Bike Tour in Chicago, where hidden gems and insider tips await those who dare to pedal off the beaten path.
★ 4.9“Gabriel is a very resourceful guide!”
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48 reviews3 hoursFrom $59by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
Pedal through Chicago's iconic sights with a full-day or half-day bike rental - which will lead you to the ultimate Windy City adventure?
★ 4.4“Tutto molto bello. Peccato che l’orario di chiusura è alle 18:30 e non alle 20:00 come indicato nella descrizione.”
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22 reviews1 dayFrom $23by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
Dive into Chicago's Westside on a food tasting bike tour with a guide and discover a world of flavors waiting to be explored...
★ 4.8“Great guide (Lew). The food at the stops where ok at most. I have done food tours all over the world and this was among the worst. Would have liked less biking and more information. (Although biking was fun and safe). Only 4 stops in…”
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16 reviews4 hoursFrom $99by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
Kickstart your adventure with the Chicago Lakefront Electric Bike Tour, where stunning views and landmarks await—discover what makes this experience truly unforgettable.
★ 4.5“We had such a fun time! Great way to see the lakefront!!! The bikes were easy to use and very comfortable. Will recommend to friends and family!”
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16 reviews45 minutes to 1 hour (approx.)From $69.34by Chicago E-Bikes
Embark on an exhilarating adventure through the vibrant streets of Chicago with the unique and thrilling experience of the Chicago Half Day Bike Rental.
★ 5.0“Very fun family friendly activity on lake Michigan’s waterfront. Easy to find Bobby’s bike hike. Easy path for all types of riders.”
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10 reviews4 hours (approx.)From $19.99by Bobby's Bike Hike - Chicago
Hidden within the chaos of Chicago, the Lincoln Park Bike Adventure promises an unforgettable journey filled with stunning views and hidden surprises.
★ 3.5“Moderate level of activity, good trails, recreational. Hard to maneuver around crowds, suggest to take the earlier tours as crowds get thicker as the day passes specially on the popular spots”
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8 reviewsFrom $44.10by Bike and Roll Chicago
Mingle flavors with landmarks on a Chicago family food tour by bike - a fusion of culinary delights and iconic sights awaits!
★ 4.9“Very nice tour, excellent guide and a great way to know the city and its food. Recommendable tour for families.”
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7 reviews4 hoursFrom $79by Bobby's Bike Hike-Chicago Bike, Walking and Food Tours & Bike/Kayak Rental
I plan Chicago around the water: architecture from the river, skyline from the lake, and deep dish to recover afterward.