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“Our guide Dan (dammit!) was very informative, friendly & fun! It was really fun riding through the streets of Chicago. Loved the Chicago dog & Molly’s cupcake!”
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.
“Great tour. Liam was a knowledgeable and enthusiastic guide and we learned lots on this tour. Definitely recommend to everyone!”
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 ride! Would do it again! Better than a boat tour! We both enjoyed it and learned a lot! They even had a trainee who was on her second day but was super knowledgeable as well!”
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.
“Great tour, Jeff was an awesome guide! Learned a ton about Chicago, food was all delicious and full sized servings, we had a blast. Would highly recommend!”
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.
“Hannah was a fantastic tour guide and we really enjoyed the leisurely ride through iconic landmarks and classic Chicago foods. Loved trying local beers as well. Great little stories and anecdotes that we didn’t know about the city. Thanks so much Hannah for such a…”
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.
“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”
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.
“Gabriel is a very resourceful guide!”
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.
“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…”
Discover Chicago’s highlights on a private electric bike tour along the lakefront. Perfect for sightseeing, with stunning skyline views and personalized guidance.
“Anthony was a wonderful guide! We had limited time for sightseeing, so this was the perfect tour to see the lake front highlights. The bikes were comfortable, easy to use, and cute!”
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.
“Very fun family friendly activity on lake Michigan’s waterfront. Easy to find Bobby’s bike hike. Easy path for all types of riders.”
The river runs through an architecture lesson, and the lake applauds.