Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
Overview
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.
What's Included
- Explore Millennium Park’s iconic art and architecture with stories that reveal its deeper meaning.
- Enjoy a FREE 2-hour Bike Rental or Kayak Rental as an added bonus (weather permitting)
- See Chicago’s top sights up close, with rich stories that deepen every landmark you visit.
- Walk the Riverwalk’s scenic edge as history, architecture, and culture come to life around you.
- Walking Tour of Chicago's Top Highlights and Attractions
- Marvel at the Wrigley Building’s stunning architecture as your guide unveils its rich history.
- Step beneath the Chicago Theatre marquee as your guide shares the dazzling history behind its glow.
- Your local guide brings Chicago’s stories to life with personality, insight, and charm.
- See the Art Institute through a new lens as your guide reveals the stories behind its masterpieces.
- Discover Cloud Gate’s reflective magic as your guide reveals the meaning behind the iconic sculpture
- Stroll the Magnificent Mile as your guide shares the history, style, and stories behind every block.
- Gratuities
Meeting Location
17 East Monroe Street
Chicago, IL 60603, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
806 Michigan Avenue
Chicago, IL 60611, USA
The iconic Chicago Water Tower is the end point of your Chicago Walking Tour.
What To Expect
Book Online
Safe & secure • Easy breezy • Hassle-free
Millennium Park
15 minutes • Admission Ticket Free
The Magnificent Mile
10 minutes • Admission Ticket Free
Chicago Riverwalk
15 minutes • Admission Ticket Free
Crown Fountain
5 minutes • Admission Ticket Free
The Chicago Theatre
10 minutes • Admission Ticket Free
Historic Water Tower
10 minutes • Admission Ticket Free
Cloud Gate
10 minutes • Admission Ticket Free
The Art Institute of Chicago
10 minutes • Admission Ticket Free
Holy Name Cathedral
10 minutes • Admission Ticket Free
Jay Pritzker Pavilion
5 minutes • Admission Ticket Free
Daley Bicentennial Plaza
10 minutes • Admission Ticket Free
Palmer House Hilton Historic Lobby
10 minutes • Admission Ticket Free
Bobby's Bike Hike - Chicago Bike, Walking & Food Tours (pass by)
Additional Info
- Confirmation is instant and will be received at time of booking
- Wheelchair accessible
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Top10Adventures® rated this tour its highest-level Traveler’s Choice Award each year since 2002.
- Our groups have exclusive VIP access to locations we visit.
- Operates in all weather conditions, please dress appropriately
- This tour/activity will have a maximum of 18 travelers
Frequently Asked Questions
(7)Q: What is the cancellation policy for the Chicago Walking Tour of Highlights with Free Bike or Kayak Rental?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-3332P28
Traveler Photos

Reviews
Average 5.00 out of 5 stars based on 6 adventurer reviews collected by Top10Adventures® and partner sites such as Cool Destinations and TripAdvisor
Additional Info
Similar Adventures & Tours

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM)...
$34

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included &...
$100

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism...
$34

Chicago Favorites Ultimate Food and Walking Tour
The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the...
$83.99
Adventurers Who Bought This Adventure Also Bought

Chicago River 90-Minute Architecture Tour
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...
$44

Chicago Crime and Mob Bus Tour
Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....
$48

Chicago Lake and River Architecture Tour
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...
$44

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...
$27





