Downtown Chicago Loop Walking Tour (Private)
Jarrett
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.
Departure Point
- 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)
- Human tour guide - English
Points of Interest
Stop At: The Chicago Theatre175 N State St, , Chicago, IllinoisStep 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.Duration: 10 minutesStop At: Marshall Field And Company Building111 N State St, Chicago, IllinoisExplore 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.Duration: 10 minutesStop At: Skydeck Chicago - Willis Tower233 S Wacker Drive, Chicago, IllinoisLook 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.Duration: 10 minutesStop At: Daley Center48 W Washington St Chicago, IL, , Chicago, IllinoisStand 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.Duration: 10 minutesStop At: Millenium ParkN Clinton St, Chicago, IllinoisWalk 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.Duration: 10 minutesStop At: The Art Institute of Chicago111 S Michigan Ave, Chicago, IllinoisPause 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.Duration: 10 minutesStop At: The L Station186 North Wells Street, Chicago, IL 60606Watch 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.Duration: 10 minutesStop At: Route 66198 S Michigan Ave, , Chicago, IllinoisStand 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.Duration: 10 minutesStop At: Chase Tower10 S Dearborn St, Chicago, IllinoisStand beneath the sweeping curve of Chase Tower, one of Chicago’s most striking modern skyscrapers.Duration: 10 minutesStop At: City of Chicago - City Hall121 N La Salle St, Chicago, IllinoisAdmire the grand neoclassical design of Chicago City Hall, a symbol of the city’s civic pride and resilience.Duration: 10 minutesAdditional Information
- 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
- Visits to major landmarks including the Chicago Theatre, Millennium Park, Willis Tower, and more
- Guided walking tour of the Chicago Loop led by a knowledgeable local guide
- Insider stories about Chicago’s Great Fire, skyscraper innovations, and urban design evolution
- Architecture and history commentary throughout the route
- Opportunities for photos at Chicago’s most iconic sites
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.
Departure Point
- 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)
- Human tour guide - English
Points of Interest
Stop At: The Chicago Theatre175 N State St, , Chicago, IllinoisStep 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.Duration: 10 minutesStop At: Marshall Field And Company Building111 N State St, Chicago, IllinoisExplore 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.Duration: 10 minutesStop At: Skydeck Chicago - Willis Tower233 S Wacker Drive, Chicago, IllinoisLook 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.Duration: 10 minutesStop At: Daley Center48 W Washington St Chicago, IL, , Chicago, IllinoisStand 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.Duration: 10 minutesStop At: Millenium ParkN Clinton St, Chicago, IllinoisWalk 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.Duration: 10 minutesStop At: The Art Institute of Chicago111 S Michigan Ave, Chicago, IllinoisPause 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.Duration: 10 minutesStop At: The L Station186 North Wells Street, Chicago, IL 60606Watch 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.Duration: 10 minutesStop At: Route 66198 S Michigan Ave, , Chicago, IllinoisStand 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.Duration: 10 minutesStop At: Chase Tower10 S Dearborn St, Chicago, IllinoisStand beneath the sweeping curve of Chase Tower, one of Chicago’s most striking modern skyscrapers.Duration: 10 minutesStop At: City of Chicago - City Hall121 N La Salle St, Chicago, IllinoisAdmire the grand neoclassical design of Chicago City Hall, a symbol of the city’s civic pride and resilience.Duration: 10 minutesAdditional Information
- 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
- Visits to major landmarks including the Chicago Theatre, Millennium Park, Willis Tower, and more
- Guided walking tour of the Chicago Loop led by a knowledgeable local guide
- Insider stories about Chicago’s Great Fire, skyscraper innovations, and urban design evolution
- Architecture and history commentary throughout the route
- Opportunities for photos at Chicago’s most iconic sites
Need To Know Info
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and Savings