Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Recommended by 99% of travelers
Badge of Excellence
Chicago, USA
- 3 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
- Spot the city's important landmarks and monuments
- Learn about Chicago history and culture
- Enjoy a relaxed route that's entirely on bike paths
- Fun, safe experience, perfect for families
What's Included
- 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.
- Named Top 20 Tour in the World by TripAdvisor—experience why guests rave about Bobby’s Bike Hike!
- $10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
- Food and drinks
Meeting and Pickup
Meeting point
- Bobby's Bike Hike - Chicago Bike, Walking & Food Tours540 N Lake Shore Dr, Chicago, IL 60611, USA
Arrive to your Chicago Bike Tour at 540 N. Lake Shore Drive (entrance on Ohio Street). Walk through the driveway (tunnel) to enter our location. Arrive 15 minutes early.
End point
This activity ends back at the meeting point.Itinerary
1
Millennium Park
20 minutes • Admission Ticket Free
2
Clarence F. Buckingham Fountain
15 minutes • Admission Ticket Free
Lakefront Trail (Pass By)
3
Museum Campus
5 minutes • Admission Ticket Free
4
Navy Pier
5 minutes • Admission Ticket Free
5
Northerly Island
15 minutes • Admission Ticket Free
Soldier Field (Pass By)
6
Chicago Riverwalk
5 minutes • Admission Ticket Free
7
The Chicago Theatre
5 minutes • Admission Ticket Free
8
Shedd Aquarium
15 minutes • Admission Ticket Free
9
Grant Ulysses Park
20 minutes • Admission Ticket Free
Field Museum (Pass By)
12th Street Beach (Pass By)
10
Cloud Gate
5 minutes • Admission Ticket Included
11
Jay Pritzker Pavilion
5 minutes • Admission Ticket Free
12
Crown Fountain
5 minutes • Admission Ticket Free
13
Adler Planetarium
15 minutes • Admission Ticket Not Included
14
Daley Bicentennial Plaza
10 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Near public transportation
- Most travelers can participate
- 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
- This tour/activity will have a maximum of 15 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Pamela_F
Damn and Fran put on a great tour. We learned a lot about Chicago and got a little exercise on the way. It didn’t hurt that the day was absolutely spectacular and all the views were over. Bright blue skies. Highly recommend this tour and keep in mind it’s only 7 to 8 miles of actual biking.
Reviews
4.9
based on 253 reviews
Sort by: Most insightful
Kate_R, Jul 2026
Such a great 3-hour overview of CHI. Liam was fun, knowledgeable and helpful for novice cyclists. Highly recommend!
Response from Host, Jul 2026
Thank you so much for your wonderful review! We're thrilled to hear you enjoyed your 3-hour overview of Chicago and that Liam made the experience fun, informative, and comfortable for novice riders. It means a lot to know you'd highly recommend our Chicago Bike Tour.
We love introducing guests to the best Things to Do in Chicago, and we're so glad your Bike Tour in Chicago gave you a memorable way to experience the city's iconic sights by Bicycle. Bobby's Bike Hike is America's longest running city bike tour operator, and reviews like yours inspire us to keep creating unforgettable adventures. We hope to welcome you back for another ride the next time you're in Chicago!
Lauren_F, Jun 2026
Really fun time. Great photo ops. Get to ride around the town. We brought a 1 year old baby and he did great with the length
Response from Host, Jun 2026
Thank you for taking the time to share your experience! We're so happy to hear you had a really fun time exploring the city and enjoyed all the great photo opportunities along the way. A Chicago Bike Tour is one of the best Things to Do in Chicago, and we're glad you were able to experience so much of the city from the seat of a Bicycle.
We're especially delighted to hear that your one-year-old did so well on the tour. It's wonderful that your family was able to enjoy this Bike Tour in Chicago together and create lasting memories.
Thank you again for your recommendation, and we're honored to share that Bobby's Bike Hike is America's longest running city bike tour operator. We hope to welcome your family back for another adventure with us in the future!
Kathryn_F, Jun 2026
Molly 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.
Response from Host, Jun 2026
Thank you so much for the wonderful review! We’re thrilled to hear that Molly helped bring Chicago’s history, architecture, and neighborhoods to life through her storytelling and expertise. Creating a fun, engaging, and safe experience is at the heart of every Chicago Bike Tour, and it’s great to know Molly’s attentiveness and knowledge made such a positive impression.
We’ll be sure to share your kind words with Molly, who takes great pride in helping guests discover some of the best Things to Do in Chicago while exploring the city by Bicycle. Your recommendation means a lot to our team, and we’re delighted that your Bike Tour in Chicago was both memorable and enjoyable.
As America’s longest running city bike tour operator, Bobby’s Bike Hike is honored to help visitors and locals experience Chicago in a unique and unforgettable way. We hope to welcome you back again for another Chicago Bike Tour in the future!
Mark_B, May 2026
The 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!
Response from Host, May 2026
Thank you so much for this thoughtful review! We’re thrilled to hear that you enjoyed learning about Chicago’s history, art, architecture, and geography while taking in those breathtaking city views. One of our favorite parts of sharing this Chicago Bike Tour is showing guests how much ground can be covered by Bicycle while still keeping the ride comfortable, fun, and accessible with plenty of stops along the way.
We’re especially happy to hear Liam made such a great impression. Safety, knowledge, and creating memorable experiences are what make a great Bike Tour in Chicago, and we’ll be sure to pass your kind words along to him.
Chicago has so many incredible attractions, and we love helping guests discover unique Things to Do in Chicago beyond what you can experience by car or walking alone. Thank you as well for mentioning the comfortable bikes and photo opportunities — those memorable views are a huge part of what makes our Chicago Bike Tour special.
Bobby’s Bike Hike is passionate about our four core tenets of travel, community, health and service, and reviews like yours mean so much to our team. We hope to see you again on another Bicycle adventure in the future! 🚲😊
Endashaw_O, May 2026
The tour guides are meticulous in highlighting historical landmarks of the Beautiful city of Chicago.
Response from Host, May 2026
Thank you so much for your thoughtful review! We truly appreciate you recognizing how meticulous our guides are in highlighting the rich history and iconic landmarks of the beautiful city of Chicago. Our team works hard to ensure every Chicago Bike Tour is both engaging and informative, bringing to life the stories behind must-see locations like Millennium Park, Grant Park, Buckingham Fountain, and the stunning lakefront.
We’re thrilled that you enjoyed exploring some of the best Things to Do in Chicago with us. Experiencing the city by Bicycle offers a unique and immersive perspective, allowing you to cover more ground while still soaking in all the incredible details that make Chicago so special. It’s exactly what we aim to deliver on every Bike Tour in Chicago—a fun, active, and memorable way to connect with the city.
At Bobby’s Bike Hike, we are passionate about our four core tenets of travel, community, health, and service, and it means so much to hear that reflected in your experience. We would absolutely love to welcome you back on another adventure—whether it’s exploring more of the city on two wheels or joining us for our Bikes, Bites & Views Bicycle Tour or one of our award-winning walking and food tours.
Thanks again for riding with us—we hope to see you again soon! 🚲
Jenny_Q, Apr 2026
Straight after our arrival in Chicago we went on the bike tour with guide Lillian. We hit the jackpot! Lillian was lots of fun and very informative, we discovered areas in Chicago that I am sure locals don’t even know about! The tour took us through the city and lakeside and we felt safe at all times. It was a great way to start our trip to Chicago.
Just do it ! 😀
Response from Host, Apr 2026
Thank you so much for jumping right into a Chicago Bike Tour with us after arriving—that’s the perfect way to kick off your trip! We’re thrilled to hear that Lillian made such a strong impression. She truly has a knack for blending fun with fascinating stories, and it’s great to know you felt safe while exploring both the city streets and the beautiful lakefront by Bicycle.
Discovering hidden gems—even ones locals might miss—is exactly what we aim for on every Bike Tour in Chicago, so your feedback really means a lot. It sounds like you made the most of your time and checked off some of the best Things to Do in Chicago right from the start!
Also, fun fact: Bobby’s Bike Hike is America’s longest running city bike tour operator, and experiences like yours are exactly why we’ve been going strong for so long.
We’d love to have you join us again on another adventure next time you’re in town—there’s always more to explore! 🚲
Lisa_W, Mar 2026
Wonderful way to see the highlights of the city, learn about the architecture as well as experience beautiful views of the skyline.
Response from Host, Apr 2026
Thank you so much for your kind words! We’re thrilled to hear that you enjoyed seeing the city’s highlights, diving into its incredible architecture, and soaking in those unforgettable skyline views. That combination is exactly what we aim to deliver on every Chicago Bike Tour.
Exploring by Bicycle really does give you a unique perspective, allowing you to cover more ground while still taking in the details that make this one of the top Things to Do in Chicago. We love that the experience stood out to you as a well-rounded and memorable Bike Tour in Chicago.
Here at Bobby's Bike Hike, we’re proud to share that we’ve been ranked among the Top 15 Experiences in the country by Yelp—a reflection of amazing guests like you and our passionate guides who bring the city to life.
We’d love to welcome you back for another ride or even a different adventure next time you’re in town! 🚲
Tee_H, Mar 2026
We 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.
Response from Host, Mar 2026
Thank you so much for the wonderful review! We’re thrilled to hear Gabe’s friendly personality and great sense of humor helped make your Chicago Bike Tour such a memorable experience. It’s great that he made sure everyone was comfortable throughout the ride, because that’s exactly the kind of care we want every guest to feel on a Bike Tour in Chicago.
We’re so glad your time exploring some of the best Things to Do in Chicago by Bicycle left you wanting to come back for more. Bobby’s Bike Hike is passionate about our four core tenets of travel, community, health and service, and reviews like yours mean the world to us. We’d love to welcome you back the next time you’re in town for another adventure!
Andy_C, Feb 2026
Highlight 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.
Response from Host, Feb 2026
Thank you so much for sharing this amazing feedback! We’re thrilled to hear our Chicago Bike Tour was the highlight of your trip. Covering so much ground comfortably (yes, Chicago is wonderfully flat!) is one of the best parts of exploring the city by Bicycle, and we love that you were able to experience so many iconic spots while learning along the way.
Our guides truly enjoy bringing the city to life, and their enthusiasm for showcasing the best Things to Do in Chicago makes every Bike Tour in Chicago special. It means a lot to know they helped you discover places you might have otherwise missed — that’s exactly what we aim for on every ride!
As America’s longest running city bike tour operator, Bobby’s Bike Hike takes great pride in creating memorable, informative, and fun experiences for our guests. We’d love to welcome you back the next time you’re in town for another adventure on two wheels!
Thanks again for riding with us! 🚲
Jeffrey_B, Nov 2025
Bike 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!
Response from Host, Dec 2025
Thank you so much for riding with us! We’re thrilled to hear you had lots of fun and that your guide helped make the experience truly worthwhile. Chicago weather can be unpredictable, so we’re glad the ponchos kept everyone comfortable and the adventure rolling 🚲🌧️
Our goal is always to deliver an unforgettable Chicago Bike Tour, rain or shine, and it’s great to know this Bike Tour in Chicago still stood out as one of your favorite Things to Do in Chicago. Providing thoughtful touches like ponchos is all part of making sure every Bicycle tour is smooth, safe, and enjoyable.
As America’s longest running city bike tour operator, Bobby’s Bike Hike takes pride in creating memorable experiences no matter the conditions. We’d love to have you back again for another ride through the city soon!
kevin_H, Nov 2025
Great 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!
Response from Host, Dec 2025
Thank you for the fantastic recommendation! We’re so happy to hear you had a great experience spending four leisurely hours cycling around the city 🚲 It’s wonderful to know that York’s fun personality and deep knowledge of Chicago helped make this Chicago Bike Tour such a memorable adventure.
A relaxed Bike Tour in Chicago is one of the best ways to take in the sights, stories, and neighborhoods, and we’re glad this ranked high among your favorite Things to Do in Chicago. Exploring the city by Bicycle really lets you see Chicago from a whole new perspective.
We’re also proud to share that Bobby’s Bike Hike is recently ranked Top 15 Experiences in the country by Yelp! Thank you again for riding with us—we’d love to welcome you back for another tour the next time you’re in town.
Louise_h, Nov 2025
Very informative, relaxed and fun bike ride with York. He was great. Easy pace and very flat . Great even for novice cyclists .
Response from Host, Dec 2025
Thank you so much for the wonderful feedback! We’re thrilled to hear you had an informative, relaxed, and fun ride with York—he really does a great job of keeping the Chicago Bike Tour enjoyable for everyone. An easy pace and flat terrain are exactly what we aim for, especially to make this Bike Tour in Chicago welcoming for novice cyclists and seasoned riders alike. 🚲
We’re proud that our tours are considered some of the best Things to Do in Chicago, and it means a lot that you felt comfortable and had fun on the Bicycle throughout the ride. As America’s longest running city bike tour operator, Bobby’s Bike Hike is passionate about creating experiences that are accessible, engaging, and memorable.
We hope to see you again soon on another adventure around the city—thanks for riding with us!
Maria_D, Oct 2025
Isfun , is also historical and get to know some parts of the city that you would not have visited on your own .
Response from Host, Dec 2025
Thank you for the great feedback! We love hearing that you found the experience fun, historical, and a chance to discover parts of the city you might not have visited on your own. That blend of storytelling and exploration is exactly what makes our Chicago Bike Tour such a memorable experience 🚲.
Seeing the city by Bicycle allows you to cover more ground while still soaking in the details, and it’s no surprise this kind of Bike Tour in Chicago is often recommended as one of the best Things to Do in Chicago. From iconic sights to hidden gems, there’s always something new to discover.
As America’s longest running city bike tour operator, Bobby’s Bike Hike is proud to share Chicago’s history and neighborhoods in a way that’s engaging, approachable, and fun. Thanks again for riding with us—we hope to welcome you back for another adventure soon!
Pamela_F, Sep 2025
Damn and Fran put on a great tour. We learned a lot about Chicago and got a little exercise on the way. It didn’t hurt that the day was absolutely spectacular and all the views were over. Bright blue skies. Highly recommend this tour and keep in mind it’s only 7 to 8 miles of actual biking.
Response from Host, Oct 2025
Thank you so much for sharing your experience! We’re thrilled to hear you had such a wonderful time with Dan and Fran on your Chicago Food Tour. It sounds like you had the perfect day to enjoy the beautiful sights, stories, and a bit of exercise along the way! We’re so glad you found the ride enjoyable and approachable — just the right balance of fun and adventure.
If you’re looking for more Things to Do in Chicago, we’d love to see you again on another one of Bobby’s Bike Hike & Food Tours, whether it’s exploring Chicago’s Chinatown or joining us for another Bike and Food Tour. Thanks again for riding with us and helping us celebrate our tenets of travel, community, health, and service!
AYesenia_S, Sep 2025
Great experiencie. Best way to know Chicago. We enjoyed it so much, the staff very professional. Good weather.
Response from Host, Dec 2025
Thank you for the kind words! We’re so happy to hear you had a great experience and that you felt this was the best way to get to know the city. With good weather, professional staff, and a relaxed route, our Chicago Bike Tour really is a fantastic way to explore it all 🚲.
Seeing the city by Bicycle lets you cover so much ground while still enjoying the sights, stories, and energy that make this one of the top Things to Do in Chicago. We’re glad you enjoyed every part of this Bike Tour in Chicago.
As America’s longest running city bike tour operator, Bobby’s Bike Hike is proud to deliver memorable experiences like this every day. Thanks again for riding with us—we hope to welcome you back on another tour soon!
Karin_D, Sep 2025
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 3 tours we did in Chicago.
Response from Host, Dec 2025
Thank you for the amazing review! We’re thrilled to hear this was your favorite of the three tours you did in the city—that truly means a lot to us. Seeing so many iconic sights while picking up fun facts along the way is exactly what makes our Chicago Bike Tour such a memorable experience 🚲.
AJ will love hearing your kind words! His fun, funny, and energetic style really brings the city to life and makes exploring by Bicycle one of the most enjoyable Things to Do in Chicago. We’re so glad he helped make this Bike Tour in Chicago stand out during your trip.
At Bobby’s Bike Hike, we’re passionate about our four core tenets of travel, community, health, and service, and it’s wonderful to know that came through on your ride. Thanks again for choosing to tour with us—we hope to see you back in Chicago for another adventure soon!
LJ_P, Sep 2025
This is a rain or shine experience and I’m glad it is! It was storming when I arrived but finished by time they were done with the safety brief. AJ did a great job moving us as a group and keeping everyone safe. You do ride throughout the city on the roads, bike lanes and a dedicated bike path. The views are incredible and the history lessons along the way were fun.
I would absolutely recommend the tour!!
Response from Host, Dec 2025
Thank you for the fantastic and detailed review! We love your attitude—rain or shine really is part of the adventure, and we’re glad the weather cooperated just in time for a smooth start. AJ does an excellent job keeping groups together and safe, and it’s great to hear you felt confident riding through city streets, bike lanes, and dedicated paths during the Chicago Bike Tour 🚲.
The mix of incredible views and fun history along the way is exactly what makes this Bike Tour in Chicago such a standout experience. Exploring the city by Bicycle truly gives you a unique perspective and is easily one of the most memorable Things to Do in Chicago.
As America’s longest running city bike tour operator, Bobby’s Bike Hike takes pride in delivering safe, engaging, and unforgettable experiences—no matter the weather. Thank you so much for the strong recommendation, and we hope to ride with you again soon!
Paige_S, Aug 2025
Great history provided on an entertaining tour. Joe made sure we were safe, we made some new friends, and the tour hit much of the city’s highlights. Plus we got good exercise outside for 3 hours!
Response from Host, Dec 2025
Thank you for the fantastic review! We’re thrilled to hear you enjoyed the entertaining history, the chance to make new friends, and all the highlights you covered along the way. Joe does an excellent job keeping everyone safe and engaged, and it’s great to know that helped make your Chicago Bike Tour such a positive experience.
Getting a solid workout while exploring the city is one of the reasons riding a Bicycle is such a popular choice among the best Things to Do in Chicago. With three hours of fresh air, fun stories, and iconic sights, this Bike Tour in Chicago really delivers the full experience.
At Bobby’s Bike Hike, we’re passionate about our four core tenets of travel, community, health, and service, and your experience reflects exactly what we aim to provide. Thanks again for riding with us—we hope to see you back again soon! 🚲
Elene_B, Aug 2025
Dan was great! He safely guided us through the Chicago masses as the triathlon was happening and provided an overall amazing experience. We went to all the major spots downtown and he showed us amazing views of the city’s skyline! Was also super informative as he talked about the architecture, the Chicago flag and lots more of Chicago's history! 100% recommend to anyone visiting!
Response from Host, Dec 2025
Thank you for the amazing review and enthusiastic recommendation! We’re thrilled to hear that Dan delivered such a safe, informative, and memorable experience—especially with the added excitement of the triathlon crowds. Guiding the group smoothly through busy downtown streets while still showcasing incredible skyline views is exactly what makes our Chicago Bike Tour so special.
It’s great to know you enjoyed learning about the architecture, the Chicago flag, and the city’s rich history along the way. Exploring all the major downtown highlights by Bicycle is truly one of the most engaging Things to Do in Chicago, and this Bike Tour in Chicago offers a perfect mix of fun, education, and unforgettable views.
We’re proud to share that Bobby’s Bike Hike is recently ranked Top 15 Experiences in the country by Yelp!, and feedback like yours is a big reason why. Thank you again for riding with us—we hope to see you back on another tour soon! 🚲
Harry, Aug 2025
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.
Response from Host, Dec 2025
Thank you for the wonderful review! We couldn’t agree more—bike tours are an excellent way to explore a new city, and having a great guide makes all the difference. We’re thrilled to hear that Meredith delivered such an outstanding experience. Her knowledge, fun personality, and upbeat energy truly shine on every Chicago Bike Tour.
It’s also great to know the Bicycle and helmets were in good shape and comfortable—those details really help make a Bike Tour in Chicago smooth and enjoyable. From learning about the city to riding at a relaxed pace, this experience is easily one of the top Things to Do in Chicago.
At Bobby’s Bike Hike, we’re passionate about our four core tenets of travel, community, health, and service, and we love hearing when that commitment comes through clearly on our tours. Thanks again for riding with us—we hope to see you back out on the bike soon! 🚲
Michel_B, Aug 2025
You get to see all the touristy sights. Our tour guide Dan was so knowledgeable with a great sense of humour. Beautiful scenery. Would highly recommend
Response from Host, Dec 2025
Thank you for the great review! We’re so glad you enjoyed seeing all the iconic, must-see sights and soaking in the beautiful scenery along the way. Dan is a fantastic guide, and his deep knowledge paired with a great sense of humor really makes the Chicago Bike Tour both fun and memorable.
Exploring the city’s highlights by Bicycle is such an engaging experience and easily one of the best Things to Do in Chicago. With a relaxed pace and plenty to see, this Bike Tour in Chicago is a wonderful way to take it all in while having a great time.
If you’re ever back in town, Bobby’s Bike Hike would love to see you again on another adventure—whether it’s our Bikes, Bites & Views Bike Tour or one of our award-winning Walking and Food Tours. Thanks again for the high recommendation, and happy riding! 🚲
Ashley_T, Aug 2025
Meredith was the bomb? She knew the city like the back of her hand. She followed the safety precautions and made sure we kept up with everyone in our group. 10/10 recommend
Response from Host, Dec 2025
Thank you for the awesome review! We love hearing that Meredith “was the bomb”—she really does know the city like the back of her hand. Her strong focus on safety and keeping the group together is a huge part of what makes our Chicago Bike Tour such a great experience for everyone.
Exploring the city by Bicycle is such a fun and immersive way to see the highlights, and it’s easy to see why this Bike Tour in Chicago is often considered one of the top Things to Do in Chicago. We’re thrilled you felt comfortable, informed, and had such a great time riding with the group.
As a fun bonus, Bobby’s Bike Hike is recently ranked Top 15 Experiences in the country by Yelp!, and reviews like yours are exactly why. Thank you for the 10/10 recommendation—we hope to see you back on another ride soon! 🚲
Cynthia_P, Jul 2025
AJ was an awesome tour guide. It was a real fun day biking around the city of Chicago. I definitely recommend this tour for anyone who loves to bike and sightsee!
Response from Host, Dec 2025
Thank you for the great review! We’re so glad to hear you had a fun day biking around the city with AJ. His energy and enthusiasm really help make the Chicago Bike Tour such an enjoyable and memorable experience for guests who love to ride and explore.
Sightseeing by Bicycle is one of the most fun and active Things to Do in Chicago, and this Bike Tour in Chicago is a perfect way to take in the city’s highlights while enjoying the ride. We truly appreciate your recommendation and are happy it delivered exactly what you were looking for.
As America’s longest running city bike tour operator, Bobby’s Bike Hike is proud to create experiences that combine fun, history, and great riding. Thanks again for touring with us—we hope to see you back on another ride soon! 🚲
Jennifer_G, Jul 2025
This is a great way to get an overview of the city. Including hidden gems your won’t find on your own.
Response from Host, Dec 2025
Thank you for the great feedback! We’re so glad you enjoyed getting a broad overview of the city along with discovering a few hidden gems you might not have found on your own. That mix of famous sights and lesser-known spots is exactly what makes our Chicago Bike Tour such a memorable experience.
Exploring by Bicycle lets you see more while still feeling connected to the city, and it’s easy to see why this Bike Tour in Chicago is often recommended as one of the best Things to Do in Chicago. It’s the perfect way to get oriented and decide what you’d like to explore more deeply afterward.
As a fun bonus, Bobby’s Bike Hike is recently ranked Top 15 Experiences in the country by Yelp!, and we truly appreciate you choosing to ride with us. Thanks again—we hope to see you back on another tour soon! 🚲
James_B, Jul 2025
Excellent way to see the city, the bike shop was easy too find and we had a friendly welcome to sign the waiver and get bikes sorted. We did about 10 miles/16 km and the tour had the right balance of cycling and stops. We saw all the major and historic parts of the city and got some great photos too. Our tour guide Josh was on his first ever tour and was knowledgable, engaging and kept us to time.
Response from Host, Dec 2025
Thank you for the excellent and detailed review! We’re so glad to hear everything started off smoothly—from the easy-to-find shop and friendly welcome to getting your bikes sorted and ready to ride. That balance of riding and stops is exactly what we aim for on our Chicago Bike Tour, and it’s great to know the pacing felt just right over the 10 miles.
Seeing the city’s major and historic highlights, grabbing great photos, and experiencing it all by Bicycle is what makes this such a standout Bike Tour in Chicago and one of the most enjoyable Things to Do in Chicago. Huge credit to Josh as well—especially impressive to hear he was on his very first tour and delivered a knowledgeable, engaging, and well-timed experience.
We’re proud to share that Bobby’s Bike Hike is recently ranked Top 15 Experiences in the country by Yelp!, and feedback like yours shows why. Thanks again for riding with us—we hope to welcome you back for another tour soon! 🚲
Christopher_C, Jul 2025
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!
Response from Host, Dec 2025
Thank you for the great review! We’re thrilled to hear you had such a fantastic time and would do it again—especially love hearing that you enjoyed it even more than a boat tour. Exploring the city on a Chicago Bike Tour really does offer a fresh, active perspective and is one of the most engaging Things to Do in Chicago.
It’s wonderful to know you both learned a lot and even our trainee impressed you—that speaks volumes about the training and passion our guides bring to every Bike Tour in Chicago. Seeing the city by Bicycle keeps things fun, interactive, and memorable for riders of all experience levels.
As America’s longest running city bike tour operator, Bobby’s Bike Hike is proud to deliver consistently high-quality experiences, whether you’re riding with a seasoned guide or a rising star. Thanks again for riding with us—we’d love to have you back anytime! 🚲
Anand_S, Jun 2025
Dan was great, covered a lot of spots with a amazing views. He was also very knowledgable.
Fantastic 3 hrs spent for a moderate amount
Response from Host, Dec 2025
Thank you for the great review! We’re so glad you enjoyed spending three fantastic hours with Dan. Covering so many spots with amazing views while sharing his knowledge is exactly what makes our Chicago Bike Tour such a memorable experience.
Exploring the city by Bicycle is a fun, active, and efficient way to see the highlights, and it’s easy to see why this Bike Tour in Chicago is often considered one of the best Things to Do in Chicago—especially when you get so much value packed into the time.
At Bobby’s Bike Hike, we’re passionate about our four core tenets of travel, community, health, and service, and it’s great to hear that reflected in your experience. Thanks again for riding with us, and we hope to see you back on another tour soon! 🚲
Frank_P, Jun 2025
This tour travels through the city and while generally fine some drivers get frustrated by having to give way to a group of cyclists. The route take in much of the cities known tourist areas and also off the main tracks. York our guide ewas very good and imparted a lot of information. Much of the trip is in single file but often in groups taking up an entire lane which felt a little vulnerable at times. Bikes were ok and every effort made to find the right fit. Only a couple of small hills to negotiate.
Response from Host, Dec 2025
Thank you for taking the time to share your honest and thoughtful feedback. We’re glad to hear you found the tour to be a good way to get to know the city quickly and that York did a great job sharing information throughout the ride. His knowledge and professionalism are a big part of what makes our Chicago Bike Tour informative and engaging.
We understand your concerns about riding through busy city streets. Navigating traffic is part of experiencing an urban Bike Tour in Chicago, and our guides are trained to prioritize safety, communication, and group awareness at all times. Riding in single file when possible and regrouping when necessary is done to keep everyone together and visible, even if it can occasionally feel a bit exposed in a lively city environment.
We’re also glad to hear the bikes were comfortable and that our team worked to ensure a proper Bicycle fit. With mostly flat terrain and just a few small hills, this tour is designed to be accessible while still showcasing a wide range of areas—one of the reasons it remains a popular option among Things to Do in Chicago.
We truly appreciate your feedback, as it helps us continue to improve the experience for future riders. Thank you again for joining us, and we hope to have the opportunity to welcome you back on another tour in the future.
Elizabeth_E, Jun 2025
We had a great time! Our guide, Nic, followed a good pace and told great stories about Chicago. Nic also did a great job of engaging everyone in the group in fun and friendly ways.
Response from Host, Dec 2025
Thank you for the great review! We’re so happy to hear you had a wonderful time and that Nic helped make the experience so enjoyable. A good pace, engaging storytelling, and fun group interaction are exactly what we aim for on our Chicago Bike Tour, and it sounds like Nic delivered all of that perfectly.
Exploring the city by Bicycle is such a lively and social way to experience the sights, and it’s easy to see why this Bike Tour in Chicago is often recommended as one of the top Things to Do in Chicago. We’re glad you felt included and connected with the group throughout the ride.
As America’s longest running city bike tour operator, Bobby’s Bike Hike takes pride in creating memorable experiences led by guides like Nic. Thanks again for riding with us—we hope to see you back on another adventure soon! 🚲
jhurler, Jun 2025
This bike tour was a highlight of our trip to Chicago. York, our guide, was terrific. The tour was very informative and we learned a lot about different sights in the downtown area.
Response from Host, Dec 2025
Thank you for the wonderful review! We’re thrilled to hear this was a highlight of your trip to Chicago and that York made such a terrific impression. His depth of knowledge and engaging style really bring the city to life, and we’re glad you enjoyed learning so much about the downtown sights on this Chicago Bike Tour.
Exploring the city by Bicycle is such an immersive and enjoyable way to experience the landmarks, which is why this Bike Tour in Chicago is often recommended as one of the top Things to Do in Chicago. It’s the perfect blend of fun, history, and sightseeing.
As America’s longest running city bike tour operator, Bobby’s Bike Hike takes great pride in creating memorable experiences like yours. Thank you again for riding with us—we hope to welcome you back on another tour soon! 🚲
From $59.00
per personup to 24 hours before the experience starts (local time)
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Chicago's Ultimate City Bike Tour of Top Downtown Attractions
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