Explore Chicago's Highlights with a Guided Walking Tour & Free Rental
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Discover Chicago’s most famous sights on the Chicago Walking Tour of Highlights, perfect for first-time visitors or anyone eager to see the city’s top attractions. Over 2 hours, stroll through downtown Chicago with expert guides sharing fascinating stories about landmarks like Millennium Park, the Magnificent Mile, and the Chicago Riverwalk. Along the way, you'll uncover hidden details and local insights that bring each site to life.
This experience includes a special bonus: a FREE 2-hour bike or kayak rental, so you can explore the Lakefront Trail or paddle on Lake Michigan for unforgettable skyline views. Whether you prefer cycling or kayaking, this added perk lets you extend your adventure beyond the walking tour and see Chicago from a whole new perspective.
Join Bobby’s Bike Hike, recognized nationally by National Geographic, USA Today, and Condé Nast Traveler for storytelling and urban exploration. This tour offers a lively, engaging way to experience Chicago’s vibrant culture, stunning architecture, and rich history—all in one memorable outing.
Frequently asked questions
How long is the Chicago Walking Tour of Highlights?
The tour lasts approximately 2 hours, covering about 1.5 miles of flat terrain.
What landmarks will I see during the tour?
You'll visit Millennium Park, the Magnificent Mile, Chicago Riverwalk, Cloud Gate ('The Bean'), the Art Institute, Holy Name Cathedral, Chicago Theatre, the Historic Water Tower, and more.
Is the tour suitable for children or people with mobility issues?
Yes, the tour is wheelchair accessible and suitable for infants in strollers. Children aged 4-11 and infants 0-3 are welcome, with appropriate accommodations.
What does the free bike or kayak rental include?
You receive a complimentary 2-hour bike rental at Bobby’s Bike Hike or a kayak rental at Ohio Street Beach, valid within 3 days of your tour date, weather permitting.
Can I cancel my booking if my plans change?
Yes, you can cancel for a full refund at least 24 hours before the scheduled tour. Cancellations within 24 hours or due to weather may be subject to restrictions.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- 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.
- Discover Cloud Gate’s reflective magic as your guide reveals the meaning behind the iconic sculpture.
- 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.
- See the Art Institute through a new lens as your guide reveals the stories behind its masterpieces.
- Walk the Riverwalk’s scenic edge as history, architecture, and culture come to life around you.
- Your local guide brings Chicago’s stories to life with personality, insight, and charm.
- Step beneath the Chicago Theatre marquee as your guide shares the dazzling history behind its glow.
- Marvel at the Wrigley Building’s stunning architecture as your guide unveils its rich history.
Not included
- Gratuities
Itinerary
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Stop 1
Millennium Park is a highlight of your Chicago Walking Tour, showcasing the city's top attractions. Your guide shares stories about its transformation from industrial rail yards into a world-famous urban park. Learn why Cloud Gate’s mirrored surface was debated, how it was engineered, and the best spots for skyline photos. Discover the Jay Pritzker Pavilion's acoustic secrets and hidden art details that many visitors miss.
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Stop 2
The Magnificent Mile is an iconic stretch filled with history and impressive architecture. Your guide shares insights about how Michigan Avenue evolved into a premier shopping and cultural hub, highlighting landmarks like the Tribune Tower and Wrigley Building. Learn about the hidden design features and engineering breakthroughs that shaped this vibrant corridor.
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Stop 3
The Chicago Riverwalk offers scenic views and fascinating stories about its transformation from industrial channel to public space. Discover how the river was reversed, the stages of construction, and the art installations and ecological efforts along the promenade.
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Stop 4
Crown Fountain is a playful and innovative public art installation. Your guide explains how it blends technology, architecture, and community, with stories about the digital faces and symbolic water effects that make it unique.
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Stop 5
The Chicago Theatre stands as a cultural icon. Your guide shares stories about its architecture, history, and famous performances, revealing how it helped revitalize the theater district.
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Stop 6
The Historic Water Tower is a symbol of resilience, surviving the Great Chicago Fire of 1871. Learn about its role in city history and its architectural significance amidst modern skyscrapers.
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Stop 7
Cloud Gate, known as 'The Bean,' is a must-see Chicago landmark. Your guide shares its design story, engineering marvels, and the best photo spots, making it a highlight of your tour.
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Stop 8
The Art Institute of Chicago houses world-renowned artworks. Your guide reveals the stories behind its collection, architecture, and the significance of its sculptures and masterpieces.
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Stop 9
Holy Name Cathedral offers a peaceful and architecturally stunning stop. Learn about its Gothic Revival design, history, and role in Chicago’s spiritual life.
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Stop 10
The Jay Pritzker Pavilion is a modern architectural marvel. Your guide discusses its design by Frank Gehry, its advanced acoustics, and its role in Chicago’s arts scene.
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Stop 11
Daley Bicentennial Plaza offers a quiet retreat with scenic views. Learn about its history, design, and how it connects to Chicago’s larger park system.
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Stop 12
The Palmer House’s historic lobby is a luxurious glimpse into Chicago’s past. Discover its Tiffany ceiling, famous guests, and the story of the city’s hospitality history.
Meeting point & pickup
Meet at the start point
Meet your guide at the S. Wabash Street entrance of the historic Palmer House Hilton. Arrive 15 minutes early. The guide will wear a Bobby's Bike Hike polo with a branded paddle. Restrooms are available onsite, and then you'll begin your Chicago walking tour.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 24 hours
- May be cancelled due to bad weather
- May be cancelled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $44.99 per person
- Free cancellation
- Secure checkout with our booking partner
