Chicago
The lakefront rides: bikes-bites-and-brews food loops, neighborhood routes along eighteen miles of shoreline path and west-side foodie rides off the tourist grid. Chicago is flat, gridded and built for handlebars.
Experience Chicago’s iconic foods, neighborhoods, and lakeside views on a 4.5-hour bike tour with tastings of deep-dish pizza, hot dogs, brownies, and craft beer.
Most Popular“Kevin was a wonderful guide. He knew his history of Chicago very well. The food stops were all delicious and gave a great background of the city, as well. We felt safe throughout the tour biking down city streets, parks, and along the beach. Would…”
Explore Chicago’s lakefront neighborhoods by bike with a knowledgeable guide, visiting iconic sights, hidden gems, and scenic parks in this 3-hour small-group tour.
“We loved the lakefront tour! Vasil was a great tour guide and he had interesting stories to share. We saw a lot more from Chicago than we would have been able to discover by foot. We loved the ease of just following someone who knows…”
Discover Chicago on a 3-hour bike tour, visiting iconic landmarks along Lake Michigan, parks, and museums—an active, family-friendly way to see the city.
“Great experience. 4 hours cycling around Chicago at a leisurely pace.Our guide York was good fun and very knowledgeable about the city.Would highly recommend this tour!”
Discover Chicago's iconic flavors and sights on a 3-hour guided food tour, with free bike or kayak rentals, led by friendly, knowledgeable guides.
“Our guide Paul was great, he shared a lot of interesting information about the city and all of the places we visited. overall great tour!”
Discover Chicago's top neighborhoods, iconic sights, and famous foods like pizza, hot dogs, brownies, and beer on this 4.5-hour guided bike tour.
“We had so much fun on this tour. It was the perfect amount of biking and eating and a perfect way to explore the city. Shout out to Joe for making it such a great experience.”
Explore Chicago’s vibrant lakefront neighborhoods, historic districts, and stunning mansions on a guided 3-hour bike tour for all ages and fitness levels.
“Great way to see the city, learn some history and get some exercise”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“This was an awesome tour: great food, great company, and a fantastic tour guide. I felt very safe riding around Chicago with Gabe, our tour guide. He made the tour alot of fun with interesting and entertaining narration of the history of the areas we…”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“Amazing experience, highly recommended if you want to see Chicago from a different perspective. AJ and Kelly were great guides”
Discover Chicago at your own pace with a full-day bike rental, exploring iconic sights like Millennium Park, Navy Pier, and Wrigley Field comfortably.
“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…”
Discover Chicago’s iconic skyline and lakefront on a 3-hour guided bike tour, visiting Millennium Park, Museum Campus, and more—perfect for active explorers.
“una experiencia infaltable para conocer la ciudad! nuestra guía muy simpática y nos contaba parte de la historia de l ciudad super recomendable lo volvería hacer”
Explore Chicago at your own pace with a flexible bike rental. Ride along Lake Michigan, visit iconic sites, and enjoy scenic views—perfect for independent travelers.
“Tutto molto bello. Peccato che l’orario di chiusura è alle 18:30 e non alle 20:00 come indicato nella descrizione.”
Discover Chicago’s vibrant neighborhoods on a 4-hour bici-food tour, sampling diverse cuisines, exploring historic sights, and enjoying scenic lakeside trails.
“Excellent tour! The bikes were good and easy to ride; the food was terrific and the tour guide was attentive, funny and knowledgeable. Highly recommend!!!”
Discover Chicago’s highlights on a private electric bike tour along the lakefront. Perfect for sightseeing, with stunning skyline views and personalized guidance.
“We had a great time with Anthony. Riding the electric bikes made the tour more fun and less work. It was nice to see part of the city from a different view.”
Experience Chicago's stunning lakefront with an easy, 2-hour bike tour. Perfect for families and casual riders wanting natural beauty and city sights.
“Thanks for being my fantastic guide, dear Nora. I really enjoyed the bike tour.”
Explore Chicago on a flexible half-day bike rental, passing iconic sights like Millennium Park, Navy Pier, and Wrigley Field at your own pace for just $19.99.
“Group of 11 rented bikes. One bike half way had a mechanical issue and they were excellent in helping us.”
The river runs through an architecture lesson, and the lake applauds.