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“Absolutely perfect! Joe is so fun, knowledgeable, patient and professional! We had a wonderful tour! Perfect amount of food and drinks. Perfect amount of ride time and breaks. Gorgeous trail just all around highly recommend this tour!!!”
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.
“Booking the 10 am tour, we were in a small group of six riders with our leader, Jamal, who was knowledgeable, attentive and sweetly funny. We rode at a very leisurely pace, able to take in our surroundings safely. I especially liked our extended stop…”
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.
“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!”
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.
“I had a awesome time with Kelly and the group. We got to see a bit of Chicago and taste some delicious food on the way. Everything was well organized an dinteresting.”
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.
“Excellent tour and way of seeing the city! Really enjoyable too!”
Explore Chicago’s vibrant lakefront neighborhoods, historic districts, and stunning mansions on a guided 3-hour bike tour for all ages and fitness levels.
“Our tour guide, York, made for a very enjoyable afternoon!”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“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…”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“Brooke was an amazing tour guide. I hadn't been on a bike for awhile but it didn't take long with Brooke's reassurance to make me comfortable. She was so knowledgeable , entertaining and professional throughout the tour. The food stops were perfectly timed so that…”
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.
“A great and amazing bike tour!! A super nice guide. Thanks you so much! :)”
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.
“Muy bonita experiencia si te gusta el ejercicio, la comida y las vistas”
Discover Chicago’s highlights on a private electric bike tour along the lakefront. Perfect for sightseeing, with stunning skyline views and personalized guidance.
“Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos”
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.