Chicago Landmarks: Guided Bicycle Tour

Embark on a thrilling 3-hour bike tour of Chicago’s iconic landmarks with Bobby’s Bike Hike. Explore Museum Campus, Grant Park, Millennium Park, and more. Perfect for first-time visitors and returning guests!

Duration: 3 hours
Cancellation: 24 hours
Highlights
  • Lakefront Trail - The 18-mile Lakefront Trail has been contributing to Chicago’s cycle success since 1963. The paved path provides walkers, runners, and bicyclists with a safe and fun way to travel along the Lake Michigan, for both recreation and commuting.
  • Field Museum - The Field Museum of Natural History is one of the largest museums in…
What's Included
  • Bicycle rental included
  • Complimentary helmet provided
  • Experienced tour guide accompanies the group
What's Not Included
  • $10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
  • Food and drinks
Additional Information

Experience the most famous sites of Chicago on a lively guided bike tour! Embark on an exhilarating and educational journey with the professional tour guides of Bobby’s Bike Hike, the oldest city bike tour company in the US. Over a relaxed 3-hour bike ride, you’ll get an intimate look at Chicago’s renowned Museum Campus, Grant Park, and Millennium Park….

Location
Bobby's Bike Hike - Chicago Bike, Walking & Food Tours
North Lake Shore Drive
Walk through the driveway (tunnel) to enter our location.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(213 Ratings)
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Elene_b
Aug 24, 2025
Dan was great! He safely... - 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!
Review provided by Viator
Mtzk316
Aug 18, 2025
5 stars, 2 thumbs up - We had an amazing time on Chicago’s Ultimate City Bike Tour! This 3-hour ride was the perfect mix of sightseeing and staying active. Our guide, York, was knowledgeable, caring, and made the experience fun from start to finish. He made sure we hit all the major hotspots I had hoped for—plus a few extra surprises—and gave us plenty of opportunities to stop for photos. York mentioned we rode about 9 miles, but with all the breaks and stops along the way, it never felt overwhelming. The pacing was great, and it made the ride enjoyable for everyone. Compared to the boat tour we did about 10 years ago, this was a fresh and active way to experience the city. If you want a fun introduction to downtown Chicago, complete with history, landmarks, and great photo ops, I highly recommend this tour. It’s a fantastic way to see the city from a different perspective!
Review provided by Tripadvisor
88wyattw
Aug 15, 2025
Great experience! Great people! - Meredith was my tour guide and she was amazing! She was knowledgeable and very nice! I had such a a great time and learned so much! Would 100% recommend!
Review provided by Tripadvisor
Harry
Aug 13, 2025
Meredith is the best whoop whoop! - 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.
Review provided by Viator
Navigate17997273140
Aug 7, 2025
Loved it, great tour great guide - Dan was awesome! Very thoughtful, very knowledgeable and kind. Trip covered major high lights and had a nice mix between everything. Also appreciated that Dan waited until everyone had gathered to do his story and gave everyone the opportunity to ask all their questions. Timings were also just right with special events along the way. Bikes were sturdy, good quality, safe and had many gears. 100% would recommend!
Review provided by Tripadvisor
Michel_b
Aug 3, 2025
Great insight to Chicago - 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
Review provided by Viator
Ashley_t
Aug 2, 2025
Meredith was the bomb?... - 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
Review provided by Viator
Shirleyci6404gf
Jul 30, 2025
Don't Miss This Ultimate City Bike Tour - Celebrating a friend's milestone birthday, we reserved the bike tour. Being avid bike cruisers at home, we thought this would be a great way to see the city. Boy did we luck out with York. If all of the guides for Bobby's Bike Hike are this good, they will be in business for many years to come. York was very well informed about many things around the city, not just the landmarks on our tour. His pace was perfect, checking in with everyone in the group regularly and he made the whole experience so fun and enjoyable. So much fun that when we found out he was a guide for the Chinatown Food & Walking Tour, we signed up immediately for the next day! If you like to bike, casual or sport, this is a fun tour to select! Thank you, York, for sharing your love of the city and showing us some of the best sights!
Review provided by Tripadvisor
I6965brheathera
Jul 27, 2025
Chicago bike tour was the best! - Had the best 3 hour city tour with Gabe! He was so informative and outgoing. We learned so much and had many laughs. 5 stars for Gabe!
Review provided by Tripadvisor
Cynthia_p
Jul 27, 2025
Awesome Tour!! - 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!
Review provided by Viator
From $60
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).