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“We had a great experience with Joe as our guide! Great view of the city and great local food. Highly recommend!!”
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.
“Dan was EXCELLENT! The only thing that I would say could be approved upon is the time spent in each location. I would have loved to have spent a little more time in Old Town! Guess I’ll have to go back!”
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.
“Bike tours are an excellent way to explore new cities/places. Having a great tour guide is important and Meredith is the best. She is knowledgeable, fun and perky! Bikes were in good shape and helmets clean.”
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.
“Brooke was an awesome guide and very informative! She kept us safe through the streets and kept a great pace! Side note, my brakes gave out on the trip and Brooke was able to quickly adjust and fix them and avoided a poor outcome! NICE…”
Explore Chicago’s vibrant lakefront neighborhoods, historic districts, and stunning mansions on a guided 3-hour bike tour for all ages and fitness levels.
“This was our first visit to Chicago and the tour was very informative. Daisy was a knowledgeable guide and did a great job.”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“Awesome time with Tryfon. This is one tour you want to take. Lots of fun and great food!! Highly recommend”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“AJ was an amazing tour guide. Good instructions before the ride for safety and tips. Almost too much food to eat!! We had a great time seeing different areas of the shoreline part of the city. Our youngest was 12 and our oldest was 57,…”
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.
“Schöne Tour.”
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.
“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!)”
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.