Chicago Downtown Private Guided Walking Tour
Active
2h - 3h
For a full refund, cancel at least 24 hours before the scheduled departure time.
Instant confirmation
Mobile or paper ticket accepted
About this experience
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.
Available options
3H:Downtown,ChicagoTheatre&Clo
Duration: 3 hours: Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate. <br/>,: Extend your walk through rich history and iconic views.<br/>Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.
2-hour: Downtown SPA, FRE
Duration: 2 hours: Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building. <br/>,: Uncover stories of resilience and architectural beauty. <br/>Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.
2-hour: Downtown ENG
Duration: 2 hours: Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building. <br/>,: Uncover stories of resilience and architectural beauty.<br/>Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.
3H:Downtown,Theatre&CloudGate
Duration: 3 hours: Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate. <br/>,: Extend your walk through rich history and iconic views. <br/>Expert-Guide: Official 5-Stars Guide who is an Expert in this kind of tours. Guide speaks fluently in chosen language - USCH001.
What's included
Private Walking Tour of Downtown Chicago’s Iconic Landmarks and Hidden Gems
5-Star Licensed Guide fluent in your chosen language
Fascinating insights into Chicago’s architecture, history, and culture
Insider tips on the best local attractions and hidden gems
Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate (in the 3H option)
- (number of attractions depends on the selected option)
Detailed itinerary
1
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.
2
Begin at the magnificent Holy Name Cathedral, a Gothic Revival masterpiece rebuilt after the Great Chicago Fire, symbolizing faith and resilience.
3
Stop 3
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.
4
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.
5
Stop 5
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.
6
Stop 6
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.
7
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.
8
Stop 8
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.
What's not included
Extended walking route to the Chicago Theatre, Cultural Center, and Cloud Gate (in the 2H option)
Entry/tickets to any attractions
Food and drinks
Available languages
Guide guide
EN
FR
ES
Important information
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!
Meeting point
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.
Important notes
Information for the customer (Know before you go)
• 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!
About Chicago
Chicago is a vibrant city known for its stunning architecture, rich cultural heritage, and world-class cuisine. Situated along the shores of Lake Michigan, it offers a unique blend of urban excitement and natural beauty, making it a must-visit destination for travelers from around the globe.
Top Attractions
Millennium Park
Millennium Park is a famous public park in downtown Chicago, known for its modern art and architecture. It's home to the iconic Cloud Gate sculpture, also known as 'The Bean'.
Park
1-2 hours
Free
Art Institute of Chicago
One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world.
Museum
2-3 hours
$25 (adults), Free for children under 14
Skydeck Chicago
Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending out from the building.
Observation Deck
1-2 hours
$28 (adults), $20 (children 3-11)
Navy Pier
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Entertainment
2-4 hours
Free to enter, individual attractions have varying costs
Wrigley Field
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
Sports
2-4 hours (game duration varies)
Ticket prices vary depending on the game and seating
Must-Try Local Dishes
Deep-Dish Pizza
A thick, buttery crust filled with layers of cheese, toppings, and tomato sauce. It's a Chicago classic and a must-try for pizza lovers.
Dinner
Contains gluten and dairy. Vegetarian and vegan options are available at some restaurants.
Chicago-Style Hot Dog
A steamed or grilled all-beef hot dog topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt, all served on a poppy seed bun.
Snack
Contains gluten and dairy. Vegetarian and vegan options are available at some hot dog stands.
Italian Beef Sandwich
Thinly sliced beef cooked in its own juices and served on an Italian roll. It's typically dipped in the juices and topped with sweet or hot peppers.
Lunch/Dinner
Contains gluten and beef. Vegetarian and vegan options are available at some Italian beef restaurants.
Chicago-Style Popcorn
A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.
Snack
Contains dairy. Vegetarian and vegan options are available at some popcorn stands.
Popular Activities
Kayaking on the Chicago River
Biking along Lake Michigan
Rock climbing at First Ascent
Picnicking in Millennium Park
Yoga in the park
Spa treatments at The Peninsula Chicago
Visiting the Art Institute of Chicago
Attending a performance at the Chicago Symphony Orchestra
Best Time to Visit
May to September
This is the best time to visit Chicago for outdoor activities, festivals, and sightseeing. The weather is warm and pleasant, making it ideal for exploring the city's parks and attractions.
15°C to 30°C
59°F to 86°F
Practical Information
Language
- Official: English
- Widely spoken: Spanish, Polish, Chinese
- English: Widely spoken
Currency
United States Dollar (USD)
Time Zone
Central Time Zone (CT) (GMT-6)
Electricity
120VV, 60HzHz
Safety Information
Overall Safety Rating: Generally safe
Chicago is generally safe for tourists, but visitors should be aware of their surroundings and take precautions to protect themselves and their belongings. Some areas of the city have higher crime rates, and visitors should research their destinations before traveling.
Important Precautions:
- • Be aware of your surroundings and keep valuables secure
- • Use licensed taxis or ride-sharing services
- • Avoid walking alone in isolated or poorly lit areas, especially at night
Getting there
By air
- O'Hare International Airport • 27 km (17 miles) from city center
- Midway International Airport • 13 km (8 miles) from city center
By train
Union Station, Ogilvie Transportation Center
By bus
Greyhound Station, Megabus Terminal
Getting around
Public transport
The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.
Taxis
Available • Apps: Uber, Lyft
Rentals
Car, Bike, Scooter
Neighborhoods
The Loop
Lincoln Park
Wicker Park
Magnificent Mile
Pilsen
Day trips
Navy Pier
2 km (1.2 miles) • Half day to full day
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Wrigley Field
10 km (6.2 miles) • Half day to full day
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
Museum Campus
3 km (1.9 miles) • Half day to full day
The Museum Campus is a 57-acre park located on the southern tip of Grant Park in Chicago. It's home to several world-class museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
Festivals
Lollapalooza • Early August (4-day festival)
Chicago Jazz Festival • Late August to early September (weekend festival)
Chicago Food Festival • Early September (weekend festival)
Pro tips
- Visit popular attractions early in the morning or late in the afternoon to avoid crowds and long wait times
- Use the Ventra card for easy and convenient payments on public transportation
- Explore the city's diverse neighborhoods and culinary scene to get a true sense of Chicago's character and culture
- Take an architecture river cruise to see the city's stunning skyline and learn about its architectural history
- Visit the city's many parks and outdoor spaces to enjoy nature and outdoor activities, even in the heart of the city
From $25
per person
Price varies by option
Secure booking
Free cancellation available
Instant confirmation
