Top Chicago Private Sightseeing Tours

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Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! As a private tour, hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your private historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

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Chicago Gangsters and Ghosts Walking Tour

2 hoursFree Cancellation

Price varies by group size

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Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.

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Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

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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.

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Chicago Jewish History Landmarks Private Guided Walking Tour

2 hoursFree Cancellation

5% savings

from

$227$216

Price varies by group size

Member Pricing

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!

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Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

3 hoursFree Cancellation

5% savings

from

$263$250

Price varies by group size

Member Pricing

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.

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Historic Pullman Private Half-Day Walking Tour

4 hoursFree Cancellation

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3 hoursFree Cancellation

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2 hours Private Evening Walking Tour with the Ghosts of Chicago

2 hoursFree Cancellation

Member Pricing

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!

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Chicago VIP Private Tour

2 to 7 hoursFree Cancellation

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This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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Private Historical Ghost Walking Tour in Chicago Lincoln Park

2 hoursFree Cancellation

5% savings

from

$869$826

Price varies by group size

Member Pricing

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.

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Private Architectural Walking Tour in Chicago Loop Landmarks

2 hoursFree Cancellation

5% savings

from

$869$826

Price varies by group size

Member Pricing

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.

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Private Architectural Walking Tour in Chicago Historic Residences

2 hoursFree Cancellation

5% savings

from

$869$826

Price varies by group size

Member Pricing

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.

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Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

9 to 10 hoursFree Cancellation

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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

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Chicago Exotic Auto Experience

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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

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Mackinac Island Private Day Tour from Chicago

16 to 17 hoursFree Cancellation

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Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages prevails. This tour includes a beautiful drive through the Midwest and a scenic ferry ride across the Straits of Mackinac, leading you to explore stunning limestone formations like Arch Rock, the historic Fort Mackinac, and the picturesque Victorian architecture downtown. Treat your taste buds to the island's world-famous fudge amidst the serene surroundings, making this a perfect escape for history enthusiasts and nature lovers alike. - Scenic drive from Chicago to Mackinac Island - Discover the unique charm of a car-free island - Explore Arch Rock and Fort Mackinac's rich history - Sample local fudge while enjoying Victorian architecture

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2 Day Private Tour Chicago to Mackinac Island Exploration

2 daysFree Cancellation

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Must-Dos in Chicago

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Top Chicago Private Sightseeing Tours

100+ results

Must-Dos in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

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