Top Chicago Private Sightseeing Tours

Private Sightseeing Tours

100+ results

Best Seller

Chicago City Private Tours

2 to 8 hoursFree Cancellation

4.7

(30)

from $199

Per group

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

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Chicago Private Custom City Tour with Hotel Pick Up

3 to 4 hoursFree Cancellation

4.9

(204)

from $539

Per group

Likely to Sell Out

Private Art Institute of Chicago Skip-the-Line Guided Tour

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

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Private Art Institute of Chicago Skip-the-Line Guided Tour

2 hours 30 minutesFree Cancellation

5.0

(304)

from $90

Price varies by group size

Private 45-Minute Chicago Skyline Helicopter Tour

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

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Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

4.8

(128)

from $849

Per group

Likely to Sell Out

Explore Chicago's legendary architecture and history.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(10,179)

from $45

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3,278)

from $28

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,266)

from $39

Likely to Sell Out

Heading out to Four Mile Crib on a beautiful day of sailing.

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

2 hoursFree Cancellation

5.0

(70)

from $508

Per group

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

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360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,263)

from $27

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and renowned stadiums. Whether you’re attending a concert, exploring historic sites, or enjoying a day at the park, our professional chauffeur service ensures a seamless and luxurious journey. With our SUV tours, you'll have the flexibility to explore at your own pace. Visit top attractions like Millennium Park, the Art Institute of Chicago, and the Field Museum. Enjoy a thrilling game at Wrigley Field or United Center or take in a concert at Allstate Arena. Our chauffeur will drop you off and pick you up at each location, providing you with the utmost convenience. Book your tour today and let us take care of the details. Travel in comfort and make the most of your time in Chicagoland with our premium SUV tour service.

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Luxury SUV 4 Hour Sightseeing Tour

from $350

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.

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Skyline, Lakefront and Millennium Park Chicago Private Day Tour

3 hoursFree Cancellation

5.0

from $169

Price varies by group size

Likely to Sell Out

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

4.0

(360)

from $63

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.

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Downtown Chicago Loop Walking Tour (Private)

2 hoursFree Cancellation

from $27

The Chicago Loop is the city's epicenter of culture, commerce, and design.

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

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Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

2 hours to 2 hours 30 minutesFree Cancellation

5.0

(4)

from $10

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

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Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

1 hourFree Cancellation

5.0

(1)

from $59

Per group

The end of our tour, and the start of The Bear, Mr Beef!

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The Bear and good food which is why we start our tour at the world famous Pequod's pizza where a hot pie will be ready waiting for us to pickup and try. Enjoy this in the pedicab as we begin our leisurely ride through the city getting an open air view of some of Chicago's cutest neighborhoods. Next up we go to Margies Candies for a Banana Split before embarking on a ride all the way from the west side to River North, crossing the Chicago River and getting some photos at the iconic LaSalle Flowers. End your epic Chicago adventure at Mr. Beef or Kasama! Your tour vehicle will be a decorated 6 seat pedicab driven by one of our knowledgeable tour guides. Comfortable for up to 4-5 adults, 6 if kids/teenagers are in the mix. Look at the photos of the cab and feel free to reach out with any questions.

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The Bear Private Pedicab Food Tour of Chicago

2 to 3 hoursFree Cancellation

5.0

(1)

from $200

Price varies by group size

Likely to Sell Out

Private Chicago Food Tour with Deep Dish and Beef Sandwich

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

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Private Chicago Food Tour with Deep Dish and Beef Sandwich

3 hoursFree Cancellation

5.0

(73)

from $225

Price varies by group size

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

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Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,847)

from $44

Likely to Sell Out

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

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Art Institute of Chicago Private Expert Guided Tour

2 hoursFree Cancellation

5.0

(99)

from $215

Price varies by group size

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.

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Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

1 hour to 1 hour 30 minutesFree Cancellation

5.0

from $10

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!

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Lincoln Park Zoo & Nature Museum Private Walking Tour

2 hoursFree Cancellation

5.0

(14)

from $275

Per group

Luxury Sedan- Lincoln Continental, Cadillac XTS, Lincoln MKT or similar

If it’s your first time in Chicago or you just have limited time, make the most of a day in the Windy City on a private driving tour. Instead of navigating public transit or waiting for ride shares, relax as a dedicated driver takes you to all the major attractions of downtown and beyond, including Navy Pier, Michigan Avenue, Wrigley Field, Millennium Park, and Museum Campus. Plus, get local insight into Chicago along the way.

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Chicago 6-Hour City Tour by Sedan

6 hoursFree Cancellation

5.0

(2)

from $960

Per group

Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.

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Frank Lloyd Wright Oak Park Architecture Tour from Chicago

5 hoursFree Cancellation

3.0

(2)

from $222

Price varies by group size

Likely to Sell Out

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,365)

from $49

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Top Attractions in Chicago

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Top Chicago Private Sightseeing Tours

100+ results

Top Attractions in Chicago

Chicago Riverwalk

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

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