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Chicago Downtown Private Guided Walking Tour

By New York City Tours
Free cancellation available
Price is ￥63,612 per adult* *Get lower prices by selecting more than 2 adults
See tickets
Features
  • Free cancellation available
  • 3h
  • Mobile voucher
  • Instant confirmation
  • Multiple languages
Overview

Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, art, and innovation. Optional: see the Chicago Theatre, Cultural Center, and Tiffany glass dome.

Tour is available in following language:
English
French & Spanish

Choose one of our excellent tour options tailored to your needs and interests:

2-hour: Downtown
Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building. Uncover stories of resilience and architectural beauty.

3-hour: Downtown, Chicago Theatre, & Cloud Gate
Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate. Extend your walk through rich history and iconic views.

This fun and history-filled tour will take you through the architectural wonders and cultural landmarks of Downtown Chicago. With a Licensed Private Guide, you'll uncover the stories behind iconic sites.

Activity location

  • The Peninsula Chicago
    • 108 East Superior Street
    • 60611, Chicago, Illinois, United States

Meeting/Redemption Point

  • The Peninsula Chicago
    • 108 East Superior Street
    • 60611, Chicago, Illinois, United States

Check availability

2-hour: Downtown ENG
  • Activity duration is 3 hours3h
    3h
  • English

Duration: 2 hours: Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building.
,: Uncover stories of resilience and architectural beauty.
Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.

Language options: English
Price details
￥63,612 x 1 Adult￥63,612
Total
Price is ￥63,612
2-hour: Downtown SPA, FRE
  • Activity duration is 3 hours3h
    3h
  • Spanish

Duration: 2 hours: Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building.
,: Uncover stories of resilience and architectural beauty.
Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.

Price details
￥73,099 x 1 Adult￥73,099
Total
Price is ￥73,099
3H:Downtown,ChicagoTheatre&Clo
  • Activity duration is 3 hours3h
    3h
  • English

Duration: 3 hours: Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate.
,: Extend your walk through rich history and iconic views.
Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.

Language options: English
Starting time: 8:00pm
Price details
￥73,099 x 1 Adult￥73,099
Total
Price is ￥73,099
3H:Downtown,Theatre&CloudGate
  • Activity duration is 3 hours3h
    3h
  • Spanish

Duration: 3 hours: Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate.
,: Extend your walk through rich history and iconic views.
Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.

Starting time: 8:00pm
Price details
￥95,029 x 1 Adult￥95,029
Total
Price is ￥95,029
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What's included, what's not

  • What's includedWhat's included
    Private Walking Tour of Downtown Chicago’s Iconic Landmarks and Hidden Gems
  • What's includedWhat's included
    5-Star Licensed Guide fluent in your chosen language
  • What's includedWhat's included
    Fascinating insights into Chicago’s architecture, history, and culture
  • What's includedWhat's included
    Insider tips on the best local attractions and hidden gems
  • What's includedWhat's included
    Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate (in the 3H option)
  • What's includedWhat's included
    - (number of attractions depends on the selected option)
  • What's excludedWhat's excluded
    Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate (in the 2H option)
  • What's excludedWhat's excluded
    Entry/tickets to any attractions
  • What's excludedWhat's excluded
    Food and drinks

Know before you book

  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Suitable for all physical fitness levels
  • Please check your email the day before the tour for important details from Rosotravel, your tour operator.
  • The itinerary depends on the selected option.
  • This is a moderate 1-2 miles walking tour, including some uneven surfaces or steps. The guide will adapt the pace to your group. Wear comfortable shoes and dress for the weather – the tour runs rain or shine!
  • To ensure a personalized experience for all guests, our private tours are limited to 25 people per guide. Larger groups will be provided additional guides.
  • Entrance tickets, food and drinks are not included in the price, but your guide will gladly recommend attractions and eateries to enhance your visit.
  • Have a special request or need accessibility support? Let us know in advance—we’re happy to help!

Activity itinerary

The Peninsula Chicago
  • 10m
Meet your guide In front of The Peninsula Chicago, 108 E Superior St, Chicago, IL 60611, United States. Please do not enter the hotel, it is only a meeting point and the staff is not informed about the tour.
Holy Name Cathedral
  • 20m
Begin at the magnificent Holy Name Cathedral, a Gothic Revival masterpiece rebuilt after the Great Chicago Fire, symbolizing faith and resilience.
Richard H. Driehaus Museum
  • 20m
Follow your guide along charming streets lined with architecture from the Gilded Age, stopping by the exquisite Richard H. Driehaus Museum, an ornate mansion reflecting the opulence of the 19th century. Learn fascinating facts about the Tribune Tower, adorned with stones from world monuments, and admire the bright white façade of the Wrigley Building, a striking icon of the city skyline.
DuSable Bridge
  • 10m
As you cross the DuSable Bridge, once a key crossing during Prohibition times, take in panoramic river views while your guide shares captivating tales from Chicago’s tumultuous past.
American Writers Museum (Pass by)
Pass by the American Writers Museum, a tribute to America’s literary legends, and conclude at the grand Millennium Monument in Wrigley Square—an elegant tribute to Chicago’s centennial.
The Chicago Theatre
  • 30m
Extend your route beyond the Millennium Monument to include the legendary Chicago Theatre, where dazzling marquees and old-world glamour echo decades of entertainment history.
Marshall Field And Company Building
  • 30m
Pause at the historic Marshall Field and Company Building, a marvel of commercial architecture and innovation, then admire the ornate Chicago Cultural Center, home to the world’s largest Tiffany glass dome—a hidden gem few visitors discover.
Cloud Gate
  • 1h
Finally, stand before Cloud Gate, affectionately known as “The Bean,” where the city’s skyline bends and dances in polished steel. It’s the perfect finale to a tour that reflects both the timeless grandeur and modern vibrancy of Chicago. Elevate your city experience with the insight and intimacy only a Private Guide can provide.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIES
    The Peninsula Chicago
    • 108 East Superior Street
    • 60611, Chicago, Illinois, United States

Meeting/Redemption Point

  • PEOPLEPEOPLE
    The Peninsula Chicago
    • 108 East Superior Street
    • 60611, Chicago, Illinois, United States

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