Chicago
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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 Scavenger Hunt by Operation City Quest
Walk around Chicago while completing the Operation City Quest scavenger hunt! Use an app to find a list of objects around the city in any order you choose and perform fun challenges for points. Collect points and take a look at your score compared to others across the country. All of our scavenger hunts have a remote host via chat to help along the way. Come out and explore with us in Chicago.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$10
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Viator
Private Transfer from Chicago (ORD) Airport to Chicago City
Take the worry out of your arrival to Chicago (ORD) Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoid the long lines for taxis on arrival, and travel in the comfort of a Premium car or minivan.
35 Minutes
Chicago
- Free cancellation
- Private tour
From
$333
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Viator
Private Tango Class Experience in Chicago
Many people join dating websites at great expense in hopes of developing a relationship with the person of their dreams. We provide dance classes as an alternative social interaction to the usually disappointing bar scene, it’s like “speed dating” to music—we call each dance with your partner a “3-minute marriage” and the results are phenomenal in cementing a relationship. Finally the Tango embrace releases endorphins and serotonin into our blood stream; the released hormones amplify pleasure and mute aches & pain. These hormones reduce chances of heart problems, help manage weight issues and create a sense of well-being. After this class your life and relationship will change forever.
2 Hours
Chicago
- Private tour
From
$200
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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
$226
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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 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
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
$131
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Viator
Iconic Photoshoot in Chicago
Capture your Chicago adventure with a professional photoshoot at the city’s most famous landmarks. Perfect for solo travelers, couples, or friends — no posing experience needed! We’ll visit: The Bean, Chicago Theatre, Riverwalk, Millennium Park & colorful street art spots. You will receive: • 100 high-resolution edited photos • Natural posing guidance • Optional outfit changes • Insider local tips for dining & exploring Come as you are — I’ll take care of the angles, lighting & magic!
1 Hour
Chicago
- Free cancellation
- Private tour
From
$250
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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
- Likely to sell out
From
$869
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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
$1,070
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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
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
Navy Pier Chicago: Private Sailboat Charter with Captain
On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include: Pricing for private groups up to 7 guests. Custom pricing available for larger groups up to 12. Anchoring in the Chicago Playpen for swim and float parties. Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties. Large open cockpit seating area. Complimentary beverages and snacks or BYO (alcohol allowed). Stereo surround sound speakers with Bluetooth connection. Fridge with ice, fully stocked kitchenware. Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse. Anchoring for concerts at Northerly Island. Kitchen, bathroom and changing room on board.
3 Hours
Chicago
- Free cancellation
- Private tour
- Special offer
From
$879
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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
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Viator
Art Boom 3 in 1 : Adults-Only Private Art Experience in Chicago
Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large canvas (24x36 inches) using our unique Shooting/Spinning technique. Each team of seven people will work together to shoot down balloons filled with paint, then watch as we spin your canvas to create mesmerizing abstract art. Art Room Experience: Indulge your inner artist as you each create your own masterpiece on a personal canvas (16x20 inches). Choose your colors, unleash your creativity, and bring your vision to life in our inviting art room. Paint: High-quality acrylic paints provided for all your artistic endeavors. Premium Clothes Protection: Keep your party attire clean and stylish with our premium clothes protection, ensuring a worry-free painting experience. Book your party at Shot of Art today and prepare for an unforgettable experience!
1h 30m
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$195
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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
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
Chicago Private Night Skyline and Lakefront Scenic Tour
Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighborhoods, and history as the skyline comes alive after sunset. Begin along the Magnificent Mile, where illuminated skyscrapers and elegant streets create a stunning urban scene. Continue to the Chicago River for reflections of iconic buildings, then visit Navy Pier with its sparkling Ferris wheel and waterfront views. Drive along Lake Shore Drive to admire the dramatic skyline over Lake Michigan, and finish at Adler Planetarium for one of the city’s most spectacular panoramic night views. This flexible, door-to-door private tour offers a relaxed, immersive way to enjoy Chicago’s landmarks and lakefront illuminated under the night sky.
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$115
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Viator
Neon Paint Therapy Experience
Paint ""Therapy"" is allowed for individuals aged 18 and over. In the case of a group, all participants must be 18 or older Engage in a vibrant explosion of creativity with the Neon Paint Therapy Experience at Shot Of Art. This immersive 30-minute activity invites adults aged 18 and over to unleash their artistic flair while surrounded by glowing neon lights and energetic vibes. Armed with water guns filled with neon paint, participants can freely express themselves on canvas and walls, creating a unique masterpiece. With premium clothes protection provided, enjoy the thrill of painting without worry. Capture the moment and let your imagination run wild in this exhilarating art session.
30 Minutes
Chicago
- Private tour
- New
From
$99
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Viator
Private Art Splash: Chicago Group Painting Experience
Discover a truly unique experience at Shot of Art! Immerse yourself in creative art sessions tailored for all occasions, from bachelor parties to corporate events. Our private rooms offer the perfect setting to unleash your creativity and celebrate with friends and colleagues. Join us for a memorable and fun-filled painting adventure unlike any other!
40 Minutes
Chicago
- Private tour
From
$70
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Viator
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
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
Museum of Illusions Chicago Admission Ticket
Step into the captivating realm of illusions, where reality is never exactly as it appears. Museum of Illusions is a one-of-a-kind, visual, sensory, and educational experience designed to engage your sense of wonder and challenge perceptions through the science behind optical illusions. We offer over 50 immersive, hands-on exhibits to explore. Our illusion rooms, installations and holograms let you defy gravity, grow and shrink your body, walk into a life-size kaleidoscope, and play tricks on your senses at every turn. It’s a mind-bending journey that deceives the senses and reveals how the brain interprets reality.
45 Minutes - 1h 30m
Chicago
- New
From
$43
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