About This Tour
This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.
Photo Gallery
See joyful visitors gathering at The Bean on our Chicago Walking Tour—a Walking Tour of Chicago packed with Top Attractions and unforgettable photo Highlights.
See the Chicago Theatre marquee on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, dazzling lights, and memorable Highlights at one of the city’s most iconic landmarks.
our participants gather beneath the iconic Chicago Theatre marquee on our Chicago Walking Tour—a Walking Tour of Chicago filled with Top Attractions, rich history, and unforgettable city Highlights.
Buckingham Fountain’s powerful water displays make it a must-see Thing to do in Chicago. Our Chicago Walking Tour features this iconic landmark, creating a memorable Walking Tour of Chicago.
Explore unique spots in Millennium Park on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, local stories, and can’t-miss Highlights in the city’s most iconic green space.
Experience the Chicago River on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, scenic views, and memorable Highlights along the city’s most iconic waterfront corridor.
TopTours Insights
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
This 2-hour walking tour takes you through Chicago's key landmarks, offering a flexible experience. It's well-suited for travelers who enjoy exploring at their own pace and appreciate the option to extend their visit with a complimentary bike or kayak rental.
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What's Included
What's Not Included
Additional Information
Meeting Point
This is the start of your Chicago Walking Tour of Chicago Attractions. Arrive 15 minutes early. Guide will be wearing a Bobby's Bike Hike collared polo with a branded paddle. Use Restroom, then you'll start your walking tour in Chicago.
Special Instructions
Please arrive 15 minutes before your scheduled Chicago Walking tour time $6per person (or more) suggested guide gratuity. (via Cash, Venmo and PayPal) Wear comfortable clothing/shoes Please use the Restroom before your arrival to your walking tour in Chicago. Bring water. Tours run rain or shine or snow Please call our main shop (312-245-9300) to redeem your 2 hour bike or kayak rental, which should take place within 3 days after you've taken your Chicago Walking Tour of Top Attractions.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
✓ Free cancellation due to bad weather
Tour Operator
Bobby's Bike, Hike & Food Tours - Chicago
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Frequently Asked Questions
Common questions about Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
Who operates this experience?
This experience is operated by Bobby's Bike, Hike & Food Tours - Chicago.
What's included?
This tour includes Explore Millennium Park’s iconic art and architecture with stories that reveal its deeper meaning., Stroll the Magnificent Mile as your guide shares the history, style, and stories behind every block., and Discover Cloud Gate’s reflective magic as your guide reveals the meaning behind the iconic sculpture. Additional amenities and services are included. All inclusions are provided by the tour operator.
How long is this tour?
The experience lasts approximately 2 hours, giving you time to fully enjoy your chosen activity.
Can I cancel this tour?
Yes, you can cancel up to 24 hours before the scheduled departure time for a full refund. If weather conditions are unsafe, the tour may be canceled by the operator. In such cases, you'll be offered a refund or reschedule.
Will I receive instant confirmation?
Yes, you'll receive instant confirmation when you book.
What to expect on this tour?
This tour experience lasts approximately 2 hours and includes all necessary equipment and guidance. You'll have access to Explore Millennium Park’s iconic art and architecture with stories that reveal its deeper meaning. and more.
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Book Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
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