Chicago
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Historic Pullman Private Half-Day Walking Tour
Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once the heart of George Pullman’s luxury railcar empire, this neighborhood is now a National Monument that beautifully preserves its 19th-century charm and revolutionary history. Wander past rows of red-brick homes, elegant civic buildings, and historic landmarks as your local guide shares the fascinating rise and fall of the Pullman Company—and how a workers’ strike here forever changed labor rights across the country. - Explore a National Monument – Walk through one of the best-preserved 19th-century industrial communities in the United States. - Visit historic landmarks – See the Pullman Administration Building, Hotel Florence, Greenstone Church, and the Pullman Historic Foundation Visitor Center. - Discover labor movement history – Learn how the famous 1894 Pullman Strike shaped the future of workers’ rights in America.
4 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$223
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Viator
Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets
Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!
3 Hours
Chicago
- Free cancellation
- Private tour
From
$263
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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
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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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 80's Movie Scavenger Hunt Adventure
Do you love 80's movies? Explore Chicago’s cinematic history with an engaging scavenger hunt that takes you through the iconic Loop and River North. This activity invites participants to connect with the city’s rich film legacy, discovering locations where classic 80's movies were filmed. Teams will tackle fun tasks like answering movie trivia, snapping photos, and solving clues, all while immersing themselves in the vibrant architecture of the Windy City. Don’t forget to channel the spirit of the 80s by dressing up and competing against friends for a memorable experience.
1 Hour
Chicago
- Free cancellation
- Private tour
- New
From
$6
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Viator
Private Chicago Suburbs Movie Sites Tour
Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits like The Dark Knight. Led by a local actor guide, explore iconic homes, schools, and streets while hearing behind-the-scenes stories and fun film trivia. Perfect for movie lovers and anyone wanting a fresh, cinematic look at the Chicago suburbs.
2 Hours - 3 Hours
Chicago
- Private tour
- Likely to sell out
From
$320
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Viator
Chicago Architecture, History and Culture Loop Walking Tour
Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago Fire, the origin of the skyscraper, the 1893 World’s Fair, Prohibition and the creation of Millennium Park. Along the way, you’ll discover some of the Loop’s most beautiful interiors, found in buildings that thousands of people walk past every day, completely unaware of what’s inside…And how things created inside those buildings shaped our current world for the better. You’ll hear the stories of the men and women--including Jean Baptiste Point du Sable, Daniel Burnham, Potter and Bertha Palmer, and Muddy Waters--who made Chicago what it is today, and those, like Jeanne Gang, who are defining Chicago’s architectural future.
3 Hours
Chicago
- Free cancellation
- New
From
$50
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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
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 Acrylic Painting Class in Chicago
Our "Fluid Art" experience is truly unique. It offers a mesmerizing journey into the world of art unlike any other. Participants are guided through an exciting process using acrylic paints, silicone, a hair dryer, and a gas burner to create captivating patterns on canvas. This dynamic and spontaneous art form is suitable for everyone, whether you're an art enthusiast or a beginner. You'll be amazed by the intricate and unexpected designs that emerge, making each piece one-of-a-kind. It's a therapeutic and enjoyable activity that guarantees a memorable artistic adventure.
45 Minutes
Chicago
- Private tour
From
$99
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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
2 Hour North Lawndale, Chicago Tour
Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like North Lawndale, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in North Lawndale - Led by knowledgeable Historian Dilla for an authentic experience
2 Hours
Chicago
- Free cancellation
- New
From
$45
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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
Logan Square Walking Tour Experience
An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chicago experience a memorable one. Get out of downtown, come and experience the neighborhoods that make Chicago the great city that it is. Looking forward to seeing you!
1h 20m
Chicago
- Free cancellation
- Private tour
- New
From
$35
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Viator
Romantic Chicago Date Night: A Creative Art Experience
SHOOTING&SPINNING IS ALLOWED FROM 18 YEARS OF AGE. In case it is a group, everyone must be 18+ What sets our Date Night Art Experience apart is the perfect blend of excitement, creativity, and connection in a vibrant, interactive setting. You won’t just paint—you’ll shoot paint-filled bombs with a BB gun, spin your canvases to create mesmerizing fluid art patterns, and splash paint freely in a dedicated studio space where messy fun is encouraged. Plus, you can customize playful "hugs" T-shirts as part of the experience. This exclusive combination of dynamic art techniques and uninhibited expression makes the experience energetic, memorable, and deeply engaging. Whether it’s your first date, anniversary, or a special night out, you’ll leave with unique, colorful masterpieces—and unforgettable memories shared in a lively, joyful atmosphere. Book now to turn your date into a creative celebration that’s truly one of a kind!
1h 50m
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$449
No similar experiences found
Viator
90 minute Chicago's Chinatown History and Culture Tour
Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks, historic streets, and cultural sites, sharing authentic stories and insights along the way. Perfect for first-time visitors or those short on time, it’s a quick yet meaningful introduction to one of Chicago’s most vibrant neighborhoods. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.
1h 30m
Chicago
- Free cancellation
From
$30
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Viator
Sip Happens: Chicago Loop Prohibition Tour
Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like Al Capone. This evening tour blends fascinating stories of gangsters and bootleggers with Chicago's vibrant cocktail and beer scene, making it an ideal experience for history lovers and cocktail enthusiasts alike. - Visit intriguing speakeasy-style venues and secret bars in Chicago's Loop - Discover the rich history of Prohibition and its impact on the city - Optional purchase of drinks and food at most stops, with recommendations provided - Perfect for history buffs and those seeking a unique night out in Chicago
1h 30m - 2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$5
No similar experiences found
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
No similar experiences found
Viator
Burning Spirits Haunted Pub Crawl
Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.
2 Hours
Chicago
- Free cancellation
- New
From
$35
No similar experiences found
Viator
Private Family Walking Tour in Chicago Loop Cultural District
This private family walking tour in Chicago introduces the cultural and architectural identity of the Loop district. You will begin in the financial center, where early skyscrapers reflect economic ambition. How did Chicago become a symbol of modern urban development? The Board of Trade Building showcases Art Deco design tied to global commerce. As you move through the Loop, theaters and public spaces reveal a vibrant cultural scene. The Cultural Center concludes the journey with artistic displays and historic interiors. This experience balances education and discovery within a city shaped by innovation. 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
$669
No similar experiences found
Viator
Lake Geneva, Anderson Japanese Gardens 1 Day Tour From Chicago
Escape the city and discover the serene beauty of the Midwest on this full-day Lake Geneva and Anderson Japanese Gardens tour from Chicago. Start your journey with a relaxing lakeside stroll through Lake Geneva, where historic estates and tranquil waters await. Enjoy optional boat rides and scenic views before heading to the renowned Anderson Japanese Gardens. There, immerse yourself in a peaceful 12-acre oasis featuring koi ponds, waterfalls, and traditional Japanese landscaping. Unlimited Bottled Water & Complimentary Snacks – Stay refreshed and energized throughout the journey. Themed Attractions with Seasonal, Adventurous & Playful Highlights – Carefully selected for excitement and discovery. Happy Family Time – Kids enjoy 50% off for a joyful and budget-friendly trip in July and August.(Prices shown are the final specials) Exclusive Travel Keepsakes – Includes a custom travel passport and share-worthy moments for your social media.
7 Hours - 9 Hours
Chicago
- Free cancellation
- Likely to sell out
From
$133
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Viator
Private 2-Hour Walking Tour: Chicago Loop Interior Architecture
Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a private tour and discover the hidden architectural treasures of Chicago with a local expert. Here are some examples of what you will enjoy: - Chicago Loop, Chicago - Chicago Cultural Center - Untitled by Picasso, - Block 37, - Marshall Field's Wholesale Store, This is a private tour just for your group.
2 Hours
Chicago
- Private tour
From
$321
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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
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