Chicago Highlights Walking Tour with Free Bike or Kayak Rental
Overview
Available languages
2 hours
Mobile ticket
The perfect tour for first timers to Chicago or those who want to explore Chicago's top attractions and highlights. Stroll through the beautiful streets of downtown Chicago and learn about the City’s rich history, colorful characters, and get insider tips. Enjoy a 2hr walking tour & receive a bonus FREE 2hr bike or kayak rental, adding value to your experience. Enjoy biking along the scenic Lakefront Trail or kayaking on Lake Michigan. Bobby's Bike Hike walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Magazine. Explore the amazing sites that Chicago made famous; Millennium Park, Chicago Riverwalk, amazing Architecture of the Wrigley Building and Chicago Theater, & Michigan Avenue dubbed ‘the Magnificent Mile’ for it’s world-renowned shopping. Bobby’s local expert guides lead you through downtown Chicago’s most iconic landmarks and share their knowledge about the City along the way. The tour covers 1.5 miles(2.25km) on easy, flat terrain.
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
2 hour Bike or Kayak Rental
Historical stories about Chicago's past
Local, Professional Tour Guide
Walking Tour of Chicago's Top Highlights and Attractions
Gratuities
What To Expect
Palmer House Hilton Historic Lobby
We’ll meet and relax in the elegantly decorated lobby of the Palmer House Hotel. You'll meet with your tour guide who will will be wearing a Bobby's Bike Hike shirt with branded paddle.
The Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States, housing an extensive collection of artworks spanning centuries and diverse cultures. Renowned for its iconic lion statues at the entrance, the museum is a cultural landmark known for its impressive exhibits, including famous masterpieces such as Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom."
Options
Chicago Highlights Walking Tour with Free Bike or Kayak Rental
Reviews
5 reviews
Total reviews and rating from Viator & Tripadvisor
Great information about Chicago
Maureen D,
Oct 10, 2025
- Review from Viator
5.00I appreciated being able to see the sites. Even more, however, I appreciated learning more about Chicago’s history and people, past and present. Thanks, Mikey, for a great tour. The bonus of the bike rental was also appreciated. We had a nice ride along the lake and even a short visit to the Lincoln Park Zoo.
Great way to see Chicago in a day!
VisitMickeyWithEmily,
Sep 30, 2025
- Review from Tripadvisor
5.00Mickey was an extremely fun and knowledgable guide! The food portions were PLENTY to fill (stuff) us for the afternoon. Great tour stops and just the right pace - highly recommend!
Vacation
VincentA796,
Dec 28, 2024
- Review from Tripadvisor
5.00Fran Fink was a wonderful tour guide and would recommend this tour if you visit Chicago, A very nice way to experience Chicago and get to know the history and FOOD of the city.
Fun facts with food
Ayesha K,
Jun 23, 2024
- Review from Viator
5.00Food was great, learning the history from our tour guide Mickey was fun. Our kids love history and they really enjoyed it!
gastronomic and informative
patrickpaulmercadom,
Mar 17, 2024
- Review from Tripadvisor
5.00The tour was great and never dull. Brooke is just the best. I priorly had in me that Chicago deep dish pizza is a Giordano piece and Paisano is new . That Italian beef is a specialty that was brought into Chicago by the Italian migrants. Lastly i never thought that the word goat referring to how it is now was coined older than me.
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