Chicago
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Chicago’s Millennium Park Self Guided Audio GPS Walking Tour
Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.
1 Hour - 1h 30m
Chicago
- Free cancellation
- Private tour
From
$10
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Chicago Willis Tower Skydeck Ticket and Audio Tour with City Walk
Entry ticket and self-guided audio tour of Skydeck and the city of Chicago are available in a separate app — the WeGoTrip app. You will receive an email from WeGoTrip with the link to download the app with the ticket and the digital guide. The digital guide includes maps, photos, scripts, and audio commentary. You will see Chicago from above and on foot with a Skydeck ticket and self-guided audio touring-app audio tour. Soak up history and panoramas of the place that Frank Sinatra called "My kind of town" and after your visit to the Skydeck, continue your journey on foot, uncovering the stories behind what you saw. Visit Millennium Park, cross the Chicago River and stroll along the Magnificent Mile
2 Hours
Chicago
- Private tour
- New
From
$79
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Viator
Private Architectural Walking Tour in Chicago Loop Landmarks
Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building and the historic Rookery Building, steeped in timeless elegance. Marvel at the striking Calder sculpture in Federal Plaza, a highlight of the city’s public art scene. Admire the innovative design of the Marquette Building, a masterpiece of the Chicago School of Architecture. Step into the luxurious Palmer House, a landmark boasting historical significance. Discover the rich legacy of the Marshall Field and Company Building, a symbol of Chicago’s commercial prowess. Finally, delve into the cultural richness of the Chicago Cultural Center, showcasing the city’s artistic diversity. Join us on this unforgettable journey through Chicago’s architectural gems in the heart of the Loop.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$869
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Viator
Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour
This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.
45 Minutes - 1h 15m
Chicago
- Free cancellation
- Private tour
- New
From
$10
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Viator
Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens
Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insights about the region. Once at Lake Geneva, you’ll have free time to explore its picturesque lakeside paths, historic estates, and even take an optional cruise. Afterward, immerse yourself in the serene pathways of Anderson Japanese Gardens, where elegant bridges, koi ponds, and peaceful landscapes await. This personalized tour offers a relaxing and enriching experience, perfect for couples, families, and small groups seeking a nature‑filled escape.
9 Hours - 10 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$1,200
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Viator
Pilsen Chicago Walking Tour: Street Art & Mexican History
Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours
1h 15m
Chicago
- Free cancellation
- Private tour
- New
From
$35
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Viator
Chicago VIP Private Tour
Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!
2 Hours - 7 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$499
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Viator
Private Cultural Walking Tour in Chicago with Lakefront Landmarks
This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects modern civic expression. What defines Chicago’s identity as a center of American innovation? Cloud Gate offers a striking reflection of skyline and sky. The DuSable Bridge stands as an engineering achievement tied to the city’s growth. Along the waterfront, Navy Pier reveals Chicago’s connection to commerce and recreation. This route connects cultural landmarks with the story of a city shaped by industry and design. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
2 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$869
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Viator
Private Architectural Walking Tour in Chicago Cultural Center
This private architectural walking tour in Chicago reveals a city shaped by cultural ambition and design excellence. You will begin at the historic Cultural Center, where a grand stained-glass dome reflects artistic heritage. How did Chicago rise from devastation to become a center of modern architecture? In Millennium Park, contemporary art and landscape design express civic identity. The Palmer House interior preserves classical elegance rooted in early urban luxury. Federal Plaza introduces bold modernist sculpture within a civic setting. The Marquette Building presents detailed mosaics that honor exploration and early American narratives. At Daley Plaza, a monumental sculpture invites reflection on artistic interpretation. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$869
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Viator
Exclusive Downtown Chicago Guided Walking Tour 12ppl Max
What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago. Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”
2h 30m
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$52
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Viator
Downtown Chicago Loop Walking Tour (Private)
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.
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$27
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Viator
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour
See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
45 Minutes - 1 Hour
Chicago
- Private tour
From
$7
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Viator
Skyline, Lakefront and Millennium Park Chicago Private Day Tour
Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories, history, and insights while guiding you through the city’s most famous sites. Begin at Millennium Park to see the iconic Cloud Gate sculpture (“The Bean”), then visit Buckingham Fountain in Grant Park for stunning lake and skyline views. Drive through downtown to admire the Willis Tower Skydeck area, then enjoy the Chicago Riverwalk and Wacker Drive for striking architectural vistas. Continue to Navy Pier with its attractions and Centennial Wheel, then take a scenic drive along Lake Shore Drive for panoramic lakefront skyline views. Conclude at Lincoln Park and North Avenue Beach for one of the city’s most memorable photo spots. This flexible, door-to-door private tour offers a relaxed and immersive way to experience Chicago’s architecture, waterfront, and vibrant urban culture.
3 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$171
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Viator
Private Shopping Tour from Chicago to Fashion Outlets of Chicago
Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.
5 Hours
Chicago
- Free cancellation
- Private tour
From
$267
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Viator
4 Hours of Chicago City Tour Sedan
Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city
4 Hours
Chicago
- Free cancellation
- Private tour
From
$640
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Viator
Chicago Custom Private Walking Tour with A Guide ( Private Tour )
Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour focuses on the exteriors of iconic monuments, including museums, while your guide shares insights into Chicago’s culture and history. If you wish to explore inside a museum, just let us know in advance and we can create a customized itinerary for you. Perfect for families, solo travelers, or couples, this tour highlights must-see landmarks and hidden gems alike. Connect with the city through local stories, insider knowledge, and expert guidance for an unforgettable experience.
2 Hours - 8 Hours
Chicago
- Free cancellation
- Private tour
From
$130
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Viator
Private Architectural Walking Tour in Chicago Historic Residences
This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where early high-rise living reshaped urban life. What architectural movements defined Chicago’s rise as a global city? Historic homes reveal craftsmanship influenced by leading architects of the modern era. Prestigious streets present a collection of preserved facades that reflect social and cultural history. Landmark residences highlight transitions from classical to modern design principles. This experience offers insight into architectural innovation and the lifestyles that shaped it. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$869
No similar experiences found
Viator
Chicago Exotic Auto Experience
This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience
3 Hours - 7 Hours
Chicago
- Private tour
- New
From
$1,800
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Viator
Mackinac Island Private Day Tour from Chicago
Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embraces a serene atmosphere where horse-drawn carriages navigate past Victorian architecture and picturesque views. Visit iconic sites such as Fort Mackinac and Arch Rock, explore quaint downtown shops, and indulge in the island's famous fudge. This tour is perfect for families, couples, and solo travelers looking for a relaxing getaway immersed in natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation
16 Hours - 17 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$1,350
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Viator
Chicago Private Neighborhoods Tour to Lincoln and Hyde Park
Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character. Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage. Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.
4 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$225
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Viator
Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries
Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower, while learning fascinating stories about Al Capone and Prohibition. An enriching experience for architecture, history and gastronomy lovers, all in one day. - 7.2 km tour through points of interest in Chicago - Discover the historical and modern heritage of the city - Explore at your own pace with captivating audio stories - Ideal for travelers in a hurry or those on a quick visit to Chicago
3 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$7
No similar experiences found
Viator
Chicago Jewish History Landmarks Private Guided Walking Tour
Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and untold stories that shaped the city’s cultural heart. Book your journey today! Tour is available in following language: English Spanish & French Highlights: • Explore Chicago’s Jewish heritage with a knowledgeable 5-Star Private Guide • Discover key Jewish landmarks and skip common tourist routes with ease • See historic monuments and hidden gems that shaped the city’s vibrant culture • Learn inspiring stories of Jewish contributions to Chicago’s art and history • Get custom tips for more cultural sites and experiences around the city Follow the footprints of Jewish history through Chicago’s vibrant streets!. On this private walking tour with Rosotravel, a Licensed Guide will tailor the experience to your interests, revealing hidden gems, fascinating stories, and historical treasures.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$227
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Viator
Private Tour Art Institute of Chicago Guided Museum
Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Art Institute of Chicago. Discover the awe-inspiring allure of Art Institute of Chicago, marvel at the grandeur of Chicago, and capture iconic moments and many more. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!
5 Hours
Chicago
- Private tour
From
$1,067
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Viator
Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game
Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing with gaming. Explore the Magnificent Mile and Cultural Mile with this unique adventure: Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.
1 Hour - 2 Hours
Chicago
- Free cancellation
- Private tour
From
$17
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