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Offered languages
- English
Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design.
Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.
What's Included
Meeting and pickup
Meet your guide in front of the Chicago Theatre at 175 N. State St. It is at the corner of State and Lake.
Tour ends at Cloud Gate (a.k.a. the Bean)
Itinerary
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1The Chicago Theatre
Step beneath the iconic marquee of the Chicago Theatre, one of the city’s most recognizable landmarks. Learn how this 1920s movie palace helped shape the Loop’s entertainment district and why its French Baroque design still dazzles visitors today.
10 minutes • Admission ticket free -
2
Explore the former Marshall Field’s department store, now Macy’s, and discover its stunning Tiffany glass ceiling and grand architecture. Hear stories of how this building became a symbol of innovation and luxury in Chicago retail history.
10 minutes • Admission ticket free -
3Skydeck Chicago - Willis Tower
Look up at one of the world’s most famous skyscrapers and the tallest building in Chicago. Learn how Willis Tower redefined the city’s skyline, its innovative “bundled tube” design, and the story behind its enduring place in Chicago’s architectural identity.
10 minutes • Admission ticket free -
4
Stand face-to-face with the mysterious 50-foot Picasso sculpture in Daley Plaza. Find out why the artist never explained his work and how it sparked Chicago’s reputation as an open-air museum of modern art.
10 minutes • Admission ticket free -
5
Walk through Chicago’s most celebrated public space. See Cloud Gate (“the Bean”), Crown Fountain, and the Jay Pritzker Pavilion, and hear how these modern designs turned an old rail yard into the city’s gathering place.
10 minutes • Admission ticket free -
6The Art Institute of Chicago
Pause by the iconic bronze lions outside the Art Institute and learn about the museum’s Beaux-Arts architecture and role in the 1893 World’s Fair. Discover how art and architecture intertwine in this Chicago landmark.
10 minutes • Admission ticket free -
7
Watch Chicago’s famous elevated trains loop around downtown and learn how this unique transit system shaped the city’s skyline, neighborhoods, and even the Loop’s name.
10 minutes • Admission ticket free -
8Route 66
Stand at the official starting point of the legendary Route 66. Hear how Chicago became the launchpad for the “Mother Road” and how it connects the city’s architectural ambition to America’s love of travel.
10 minutes • Admission ticket free -
9Chase Tower
Stand beneath the sweeping curve of Chase Tower, one of Chicago’s most striking modern skyscrapers.
10 minutes • Admission ticket free -
10
Admire the grand neoclassical design of Chicago City Hall, a symbol of the city’s civic pride and resilience.
10 minutes • Admission ticket free
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
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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
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
You can cancel up to 24 hours in advance of the experience for a full refund.
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