Explore Chicago's Loop on a Small Group Walking Tour
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Discover Chicago through the eyes of a passionate local guide on a small-group walking tour that goes beyond the usual tourist spots. As you stroll through the city's heart, you'll uncover fascinating stories, admire world-famous architecture, and learn about the events that shaped Chicago into a global hub.
With a small group of no more than 10 people, the experience feels relaxed and interactive. You'll have plenty of chances to ask questions, connect with your guide, and get insider tips on the best places to eat, drink, and explore long after the tour ends.
Whether you're visiting Chicago for the first time or returning to explore more, this tour offers an engaging introduction to the city’s rich history, vibrant culture, and stunning architecture.
Frequently asked questions
How long is the tour?
The walking tour lasts approximately 2.5 hours.
In what languages is the tour offered?
The tour is available in Spanish and English.
What is the group size?
Groups are limited to up to 10 participants.
Is the tour suitable for children?
Yes, infants (0-8) can ride in strollers, and children aged 9-15 are welcome. Participants should have at least a moderate level of physical fitness.
What is included in the tour?
A professional local guide fluent in Spanish and English.
Are tips included?
No, tips are not included and are appreciated if you enjoyed the tour.
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 2.5 hours
Check availability to see start times.
Live tour guide
Spanish
Key facts
What's included
Included
- Professional local guide fluent in Spanish and English
Not included
- Tips
Itinerary
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Stop 1
Discover the Rookery Building, one of Chicago's most iconic historic skyscrapers. Admire its stunning architecture and see the lobby redesigned by Frank Lloyd Wright. Learn how this building influenced modern skyscraper design and became a symbol of Chicago's architectural innovation.
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Stop 2
Stand before the Chicago Board of Trade Building, a masterpiece of Art Deco style and a key financial landmark. Hear about Chicago's rise as a trading hub, the history of the first futures exchange, and admire its impressive details.
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Stop 3
Admire Calder's Flamingo, the bright-red sculpture in Federal Plaza. Discover how Alexander Calder's design adds movement and color to Chicago's public art scene and learn about the city's rich collection of outdoor art.
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Stop 4
Visit the starting point of Historic Route 66. Take a photo by the iconic 'Begin Route 66' sign and hear stories about how this legendary highway symbolizes exploration and the American Dream, stretching from Chicago to California.
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Stop 5
See the exterior of the Art Institute of Chicago, renowned for its Beaux-Arts architecture and bronze lion statues. Learn about its history and the world-class artworks housed inside.
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Stop 6
Explore Millennium Park, Chicago's most famous urban space. Discover landmarks like Cloud Gate ('The Bean'), Crown Fountain, and the Jay Pritzker Pavilion, and learn how the park transformed into a top city attraction.
Meeting point & pickup
Meet at the starting point
You will find us next to the Picasso statue, look for our blue umbrella!
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 in advance
- No refund if cancelled within 24 hours of departure
- Tour may be canceled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $25.00 per person
- Free cancellation
- Secure checkout with our booking partner
