Chicago
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Private Chicago Street Food Walking Tour With A Local Guide
Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. Indulge in the iconic Chicago deep-dish pizza, renowned for its thick crust and flavorful fillings, followed by a visit to a historic eatery for the famed dipped Italian beef sandwich, a local favorite. Amidst culinary delights, marvel at architectural marvels like Cloud Gate and the Chicago Cultural Center, adding depth to your exploration. As the tour unfolds, anticipate a tantalizing surprise: a secret dish, revealed only on the day of your adventure, promising an unexpected culinary delight. This immersive experience offers not only a feast for the palate but also insights into Chicago's rich culinary heritage and architectural splendor.
3 Hours
Chicago
- Free cancellation
- Private tour
From
$308
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Viator
2 hours Private Evening Walking Tour with the Ghosts of Chicago
Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$350
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Viator
Chicago Self-Guided Walking Audio Tour
Relive this city’s most remarkable historic events while visiting the towering buildings, fascinating sculptures, and beloved public spaces built by generations of Chicago laborers who brought to life the ingenious ideas of some of the world’s most influential designers.
1 Hour - 2 Hours
Chicago
- Private tour
- New
From
$5
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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
$323
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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
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Viator
History of the Jazz Age at Chicago Art Deco Architecture Tour
Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour. Go back in history while admiring one of the epicenters of the style’s birth. Immerse yourself into the life of the Windy City between World War I and World War II, the time when the design evolved and turned into neo archaic Mesoamerican grandeur, which can’t leave anyone indifferent. Be delighted with the variety of decorations and geometrical shapes which distinguish Art-Deco from Neoclassicism. Uncover the stories behind the famous Loop district of Chicago. Delve into the atmosphere of the 1920s as you listen to more insights and facts from your enthusiastic local guide. Overview the history and pay attention to the details you wouldn’t notice without a tour. Grab the chance to get inside famous buildings and revel in the Art Deco interiors.
1h 30m
Chicago
- Free cancellation
From
$67
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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 Congress Plaza Walking Tour
Walk where a nation was born and experience the story behind America’s fight for independence. Join Rosotravel for a 2.5-hour guided walk along the Freedom Trail, crafted for travelers who want insight, emotion, and connection—not just photos. Starting at Boston Common, your Licensed Guide brings history to life at sites including the Massachusetts State House, Old South Meeting House, Old State House, Faneuil Hall, and Old North Church, ending near the Bunker Hill Monument. Through vivid storytelling and expert perspective, discover the people and events that shaped a nation. Don’t just visit Boston—understand it. Book your walking tour today. Discover Chicago’s dark past with a 5-Star Licensed Guide downtown Trace Al Capone’s rise from Riverwalk to Congress Plaza Hotel Learn how Prohibition gang wars shaped Michigan Avenue’s legacy See Chicago Theatre and Palmer House tied to crime lore Feel chills at Congress Plaza and Cloud Gate at night
2 Hours
Chicago
- Free cancellation
- Special offer
- New
From
$24
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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 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
Visit in French: The Evolution of the Skyscraper
This unique tour will give you a complete overview of Chicago's architecture. While listening to the history of the city, you will see, in chronological order, some of its oldest buildings, as well as ultra-high towers of recent construction.
2 Hours
Chicago
- Free cancellation
From
$35
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Viator
Private Shopping Tour from Chicago to Chicago Premium Outlets
Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - 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 - 6 Hours
Chicago
- Free cancellation
- Private tour
From
$295
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Viator
Architectural and Historical Private Tour in Downtown Chicago
To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.
2h 20m - 2h 30m
Chicago
- Free cancellation
- Private tour
From
$199
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Viator
Hyde Park Walking Tour History Race and Urban Change
Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development. - Walk through Hyde Park and learn about its historical significance - Visit key sites related to civil rights and urban policy - Understand the neighborhood's transformation and ongoing challenges - Perfect for history lovers and those curious about social dynamics
3 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$5
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Viator
Christmas Eve Plated Dinner Cruise on Lake Michigan
Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City Cruises’ distinctive hospitality. While onboard, experience exceptional views of Washington DC’s iconic landmarks, DJ entertainment, and festive décor. Our team will happily take care of the details, leaving you to celebrate the holidays on the Potomac River with your friends and family. Happy Holidays Includes Three-hour Christmas Eve dinner cruise on the Potomac River Chef-prepared, three-course, plated holiday menu The most breathtaking views of the nation's greatest landmarks including the Washington Monument and Lincoln Memorial DJ entertainment Complimentary coffee, hot tea, and iced tea
3 Hours
Chicago
- Free cancellation
From
$198
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Viator
Chicago to Mackinac Island Scenic Tour
Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with 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
- New
From
$795
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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
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
No similar experiences found
Viator
Latin Libations Mixology Experience
Unlike typical cocktail classes, this experience is infused with culture, storytelling, and hospitality rooted in Latin and Caribbean traditions. Hosted by Chef & Mixologist Inez Melendez at the warm, welcoming Chicago Mama’s Kitchen, you’ll learn more than just how to mix a drink—you’ll explore the origins of ingredients, the legacy of spirits like rum and agave, and the personal stories behind each cocktail. This is a true culinary journey in a glass—designed to connect people through flavor, rhythm, and shared experience. With small group sizes, hands-on participation, and a fun, relaxed vibe, it’s not just a class—it’s a celebration.
1h 30m
Chicago
- Free cancellation
- New
From
$100
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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
Chicago Early Skyscraper Walking Tour in the Loop
Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.
2 Hours
Chicago
- Free cancellation
- New
From
$39
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Viator
Classic Chicago Food Lovers Tour in River North
Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of the place while trying out the best dishes to illustrate different cuisines. Follow your guide’s advice not to get lost in a great diversity of options and enjoy the most peculiar delicacies including deep dish pizza, Italian beef, and hot-dogs. Feel your stomach with delight and your head with new information as you walk and learn something new with every step you make. - Eat your way through the River North neighborhood to get a real taste of the City by the Lake. - Combine walking tour with history insights and culinary tips from your guide. - Enjoy a small group for better personalized experience. - Benefit from your guides expertise and learn more about restaurants and cafés of Chicago.
2 Hours
Chicago
- Free cancellation
From
$136
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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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