Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Overview
Available languages
3 hours
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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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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.
What‘s Included
Named Top 20 Tour in the World by TripAdvisor—experience why guests rave about Bobby’s Bike Hike!
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.
Bikes, helmets, child equipment, and all gear included on your Chicago Bike Tour
$10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
Food and drinks
Options
Daytime Chicago Bike Tour
Reviews
235 reviews
Total reviews and rating from Viator & Tripadvisor
Great tour!!
Tee H,Mar 21, 2026
- Review from Viator
5.00We had Gabe as our tour guide. He was extremely friendly and had a great sense of humor and made sure the group was comfortable before we took off and during our travels. The next time I’m in town, I would definitely do another tour with this company.
Highlight of our trip to Chicago
Andy C,Feb 17, 2026
- Review from Viator
5.00Highlight of our trip to Chicago - we covered so much ground (all on the flat) and learned so much. Got to see places you may well miss otherwise. Guides were fantastic, friendly and informative, great enthusiasm for the city.
Great bike tour!
Jeffrey B,Nov 14, 2025
- Review from Viator
5.00Bike trip was lots of fun, tour guide was great and made the trip worthwhile. It rained part way through our trip but the guide had ponchos for everyone!
Great 4 hours cycling around Chicago
kevin H,Nov 2, 2025
- Review from Viator
5.00Great experience. 4 hours cycling around Chicago at a leisurely pace.Our guide York was good fun and very knowledgeable about the city.Would highly recommend this tour!
York bike ride
Louise h,Nov 1, 2025
- Review from Viator
5.00Very informative, relaxed and fun bike ride with York. He was great. Easy pace and very flat . Great even for novice cyclists .
Bike tour of Chicago
RichardE2217,Oct 22, 2025
- Review from Tripadvisor
5.00Very easy to organise and an excellent way to explore downtown Chicago. Our guide, Gabe was very friendly and extremely knowledgeable leading us on a three hour tour of many of the notable sights. Well worth a try.
Excellent Exploration of Chicago!
Culture569976,Oct 21, 2025
- Review from Tripadvisor
5.00This was One of the high lights of my Chicago trip! Exceptional experience! Our guide was the absolute best! Learned so much!
Fun way to experience Chicago and a great value too!
Fmandan,Oct 16, 2025
- Review from Tripadvisor
5.00My daughter and I decided to visit Chicago and wanted a fun way to see the city. We couldn't have picked a more ideal day or way to achieve that. We arrived at Bobby's Bike Hike, which was easy to find and in a great location. Our guide, Lillian (I believe was her name) was fantastic. She really knew the city and the history, but more impressive was her kind nature and ability to keep everyone together and safe during the ride. If you're in moderately good shape, this is a very "do-able" ride and the bikes are excellent. It was a great way to see the beauty of Chicago and get a little exercise at the same time!
Loved it!
H1821YSsandrar,Oct 15, 2025
- Review from Tripadvisor
5.00We had a great morning touring Chicago with our guide, Joe. He shared loads of local knowledge in a fun & informative way. We were a big group but he kept us all safe on the busy city roads then further out towards parkland. We were all able to hear him clearly and it was good group of people from all over. Joe took loads of pictures for us. It was a fun way to discover Chicago and we totally recommend it. Mostly flat and not demanding. 5 stars 🤩
Fun and educational
Maria D,Oct 14, 2025
- Review from Viator
5.00Isfun , is also historical and get to know some parts of the city that you would not have visited on your own .
From US$59.00
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Operated by Bobby's Bike, Hike & Food Tours - Chicago