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“A must when you come to Chicago! Tour was great and chill! Got to me meet new people and check out new places. Our tour guide Joe was great!”
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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“So many different neighborhoods with unique histories close to downtown. Guides Fran & Dan kept our group together and explained about the fire of course, the World's Fairs, Abe Lincoln's lucky shoe & why his statue is so tall, Hugh Hefner's former mansion - and…”
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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“We had a fantastic time on this tour. Got to see a lot of sites, and learned some fun facts about the city along the way. AJ was our guy and is such a fun, and funny tour guide. This was our favorite of the…”
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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! Saw so much of Chicago and had some excellent food and beers. Our tour guide Fran was awesome - thank you!!”
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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“We had a fantastic tour. Daisy was an amazing guide with fun informative and relevant information about the city she loves. Duration of 3 hours was perfect! The bikes were maintained And we were given adequate instructions on the bikes themselves and the content of…”
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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“Great way to see a non-touristy side of Chicago. Enjoyed riding through the neighborhoods and sampling diverse foods. Great for foodies who want exercise as well”
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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“Seeing the different neighborhoods while riding a bike and tasting different foods.Great activity for the whole family.”
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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“Amazing guide and tour. Bikes were excellent and gave us chance to see so much of the city you wouldn’t access on any other tour. Loved it!!”
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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“Joe was an amazing guide: professional, fun, engaging. The bikes were perfectly maintained! The route was lovely and the food was awesome (I appreciate the focus on smaller awesome non-chain vendors… we even happened to meet two owner!)”
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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“Beautiful ride mostly on bike trails and mostly lakeside. Anthony provided interesting info on the stops.”
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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“Group of 11 rented bikes. One bike half way had a mechanical issue and they were excellent in helping us.”
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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“Great guide (Emma) - would suggest spreading out the food stops. We enjoyed it very much.”
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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.