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“I had an afternoon to myself and live the outdoors so I booked the 4 hr bike, bites, and brews tour. I had a great time and was completely comfortable doing this tour by self as the guide was great and others in the group…”
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.
“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…”
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 guide was awesome! Very knowledgeable and passionate about Chicago as well as our safety! We loved everything about our Bike Hike. The bikes Were easy to handle for all ages and skills. It’s a fun way to see and travel through the city! Think…”
Experience Chicago’s diverse neighborhoods and cuisines on this 4-hour bike tour, sampling local foods, enjoying scenic views, and exploring vibrant districts.
“My husband and I really enjoyed this tour. Our guide, Joe, was knowledgeable, and friendly. After a brief safety session, he led us through the city and through a variety of towns. He gave us information about the areas at stoplights and during our meals.…”
Explore Chicago on a guided bike tour blending top sights with delicious local foods. Perfect for first-timers and families seeking authentic experiences.
“Lots of fun. Everyone in the family loved the tour and it was the highlight of the trip to Chicago. Chloe did a fantastic job.”
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.
“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.
“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.