Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Overview
Available languages
3 hours
Mobile ticket
Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle tour company, on this exciting and informative adventure. Over the course of a 3-hour bike ride (traversed at a nice leisurely pace), you’ll get up close and personal with Chicago’s legendary Museum Campus, Grant Park, Chicago Riverwalk, Lakefront and Millennium Park. You’ll become intimately familiar with Soldier Field, The Adler Planetarium, Buckingham Fountain, The Pritzker Pavilion, and Cloud Gate (the formal name of Chicago’s dearly-beloved “Bean”). This tour is perfect for first time visitors looking to see all of the classic hotspots, and for returning guests looking to understand more about the landmarks they know and love. Hop on two wheels, and come make memories that are sure to last a lifetime! All equipment included on this Bicycle Tour of Chicago.
Additional Info
Public transportation options are available nearby
Suitable for all physical fitness levels
This Chicago Bike Tour is appropriate for most ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
Please note: children must be strong, capable riders and be able to bike for 9 miles
All equipment included: Bicycles, Helmets, and Child Equipment
What To Expect
Millennium Park
Millennium Park is where modern Chicago shows off. On our Chicago Bike Tour, you’ll glide into this world-famous public space where bold architecture, public art, and skyline views collide. Insiders know to look beyond Cloud Gate—notice how the park was built over active rail lines, transforming industrial space into one of the city’s greatest civic achievements. On our Bicycle Tour in Chicago, you’ll hear how Millennium Park became a global symbol of Chicago’s creativity and reinvention. From the Jay Pritzker Pavilion’s sweeping steel design to interactive art installations, it’s a masterclass in urban innovation. Among the top Things to do in Chicago, seeing Millennium Park by bike lets you experience its scale, energy, and cultural impact in a way that feels dynamic and alive.
Clarence F. Buckingham Fountain
Buckingham Fountain is pure Chicago grandeur. On our Chicago Bike Tour, you’ll roll into Grant Park and see one of the largest fountains in the world set against a skyline that feels cinematic. Insiders know to time it near the top of the hour when the central jet soars skyward—creating the kind of photo moment that defines summer in the city. On our Bicycle Tour in Chicago, you’ll hear how this Beaux-Arts masterpiece symbolizes Lake Michigan and the city’s connection to the water. It’s not just decorative—it’s civic pride in motion. As one of the most iconic Things to do in Chicago, experiencing Buckingham Fountain by bike lets you take in its scale, symmetry, and skyline backdrop in a way that feels immersive and unforgettable.
Options
Daytime Chicago Bike Tour
What‘s Included
Named Top 20 Tour in the World by TripAdvisor—experience why guests rave about Bobby’s Bike Hike!
Bikes, helmets, child equipment, and all gear included on your Chicago Bike Tour
Fun, local guides share insider tips, history, food, & hidden gems for an unforgettable experience.
See the best of Chicago's downtown attractions & architecture on this scenic, culture-packed ride.
$10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
Food and drinks
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
250 reviews
Total reviews and rating from Viator & Tripadvisor
Riding through the cities and history of Chicago
Kathryn F,Jun 10, 2026
- Review from Viator
5.00Molly was an outstanding guide as she led us through both the history snd the streets of Chicago. Her knowledge was immense and the stories she shared made the city come to life. She was very aware of our safety and was continuously checking to make sure all was well. I highly recommend Bobby’s Bikes and especially Molly for Chicago bike tours.
Three wonderful hours in Chicago
richarla22,Jun 10, 2026
- Review from Tripadvisor
5.00This tour was a great way to get to know the city with some historical perspective. Our guide, Molly, was the best! She is native to Chicago and was a phenomenal guide. I highly recommend. My husband and I are already planning our next bike adventure.
Cleaners are Toppers.
pieterbD8433ZG,Jun 5, 2026
- Review from Tripadvisor
5.00Cleaners are really great, especially Tsabika.
Comprehensive bike tour
Matthew G,May 26, 2026
- Review from Tripadvisor
5.00Gabe was great with leading our group of various ages on a very busy holiday weekend!
Great way to experience Chicago
Mark B,May 20, 2026
- Review from Viator
5.00The trip includes a lot of very interesting information on Chicago’s history; art; architecture and geography. The views of the city were breathtaking with many opportunities to take pictures. The tour makes multiple stops so the cycling isn’t too challenging. We were able to cover a lot of ground and see several spots that would have been much more difficult to see by car or simply walking. The bikes were very comfortable. Liam, our guide was excellent. He always made sure we were safe and was extremely knowledgeable about the areas we covered. Highly recommend this tour and Liam!
Book It!
CarolineGal123,May 16, 2026
- Review from Tripadvisor
5.00This was one of the highlights of our trip!! Definitely recommend. Great way to see (and learn about) the city. Going into it we were like…3 hours seems kinda long…but it wasn’t—totally the perfect amount of time. Our guide Dan was the best!!
Great way to learn all about Chicago and the iconic food!
Bonnie S,May 11, 2026
- Review from Tripadvisor
5.00Our tour guide Brendan was awesome! We heard all about Chicago history. Very interesting and fun stories. The food was great. and plentiful.One wish is more water or maybe even offer a beer. We would definitely recommend this tour to friends.
Liam was a great guide. We enjoyed the cycling the information and the beautiful city
Prayna P,May 10, 2026
- Review from Tripadvisor
5.00Well organised ands informative. Good quality bikes and excellent route. Got to see the beautiful city and its architecture
Awesome Ride
Endashaw O,May 5, 2026
- Review from Viator
5.00The tour guides are meticulous in highlighting historical landmarks of the Beautiful city of Chicago.
Great way to see around the City and then see where you want to go back to
Frances O,May 3, 2026
- Review from Tripadvisor
5.00Fantastic trip Bikes were in great condition Liam our guide was so knowledgeable about all things Chicago He also tailored the speed of the trip to the level of experience of the bikers He guided us expertly around the City some quite areas but also some busy intersections Could not rate him highly enough
Related Experiences
Operated by Bobby's Bike, Hike & Food Tours - Chicago