Top Chicago Private Sightseeing Tours

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Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the Field Museum and Adler Planetarium, will zip right along the waters of Lake Michigan, and will stop to soak up picture-perfect views of the Chicago skyline.

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Chicago Lakefront Electric Bike Tour

45 minutes to 1 hourFree Cancellation

Member Pricing

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

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Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

Member Pricing

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

Price varies by group size

Member Pricing

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!

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Private Holiday City Tour

3 hoursFree Cancellation

Member Pricing

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

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Chicago Self-Guided Audio Tour

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Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

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Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

Member Pricing

Private Chicago History Museum Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly history, gorgeous murals, and 300-year-old oak trees; and, at your journey’s end, find yourself rewarded by the sight of an architectural gem. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Join the game! Highlights include: • Explore Merz Apothecary, Gene's Sausage Shop and Delicatessen, Lincoln Square Mural and lesser-known places. • Enjoy a uniquely crafted story brought to you by our top-notch/gifted/talented writers. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt. After your booking you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

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Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

1 hour 50 minutes to 2 hours 20 minutesFree Cancellation

Price varies by group size

Member Pricing

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

Member Pricing

Route 66 Multi Day Tour from Chicago to Los Angeles

14 daysFree Cancellation

5% savings

from

$10$10

Member Pricing

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

2 to 4 hoursFree Cancellation

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

1 to 30 days

4.0

(370)

from $84

Likely to Sell Out

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

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The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

4.0

(59)

from $32

Special Offer

Chicago Chinatown: Dragon Kings Puzzle Adventure

Embark on an interactive adventure through Chicago’s Chinatown with the Dragon Kings Quest, a mobile escape game blending urban exploration, riddles, and local legends. Use your phone and the Questo app to follow clever clues, unlock stories, and discover must-see landmarks from Chinatown Square and colorful murals to hidden gems and Ping Tom Memorial Park. Go at your own pace, play solo or with friends, and experience the city in a totally new way. Fun for all ages—perfect for families, date nights, or teams seeking a unique outdoor challenge!

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Chicago Chinatown: Dragon Kings Puzzle Adventure

48 minutes to 1 hour 18 minutesFree Cancellation

3.8

(10)

from

Price varies by group size

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

Member Pricing

Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that works best for you. Discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and stop and start the tour whenever you like.

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Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

50 minutesFree Cancellation

Special Offer

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.

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Chicago Private Night Skyline and Lakefront Scenic Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of the world’s first skyscrapers and venture inside a collection of the city’s most influential and iconic buildings. Your expert local guide will share captivating stories about the rise of Chicago, the Great Fire, and the visionary architects whose bold designs shaped the skyline we know today. This tour offers the perfect mix of history, design, and city energy—a must for architecture lovers and curious travelers alike. - Explore the birthplace of the modern skyscraper - Step inside landmark buildings like The Rookery and the Palmer House - Learn about the Great Chicago Fire and its lasting impact on the city - Enjoy a relaxed pace through Chicago’s vibrant downtown Loop

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Private Chicago Architecture Walking Tour

3 hoursFree Cancellation

Member Pricing

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

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Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

Special Offer

Chicago Art Heist: Millennium Park Puzzle Adventure

1 hour 35 minutesFree Cancellation

4.0

(10)

from

Price varies by group size

Member Pricing

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

5% savings

from

$27$26

Member Pricing

Resilience and Revolution: Audio Tour of Chicago’s Black History

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activism that transformed both the city and the nation. From Underground Railroad stations to civil rights battlegrounds, you’ll discover how Chicago became a beacon for those seeking freedom and opportunity. Starting at the site of Jean Baptiste Point DuSable’s mansion near the Chicago River, you’ll follow the footsteps of the city’s founder: a Black man who established Chicago’s first trading post in the 1770s. You’ll walk through the heart of the Loop, exploring sites where pioneering entrepreneurs like John Jones built businesses that became platforms for activism. The tour ends at Grant Park, where Barack Obama delivered his historic presidential acceptance speech in 2008 – a moment that represented the culmination of generations of struggle.

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Resilience and Revolution: Audio Tour of Chicago’s Black History

2 hours to 2 hours 30 minutesFree Cancellation

5% savings

from

$15$14

Member Pricing

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

Discover the creative side of Chicago beyond the city limits with this small-group tour of suburban hidden gems! Visit charming historic districts, offbeat local landmarks, striking public art, scenic waterfronts, and under-the-radar eateries as your expert guide shares insider stories you won’t find in guidebooks. With transport included and group size kept small, it’s a relaxed, camera-worthy way to explore unique neighborhoods, architectural treasures, and distinctive local culture. Ideal for repeat visitors, adventure seekers, or anyone curious to see more than the Magnificent Mile.

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Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

8 to 12 hoursFree Cancellation

Price varies by group size

Member Pricing

GPS Audioguide app: From Loop to Millennium Park (Offline).

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

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Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

3 hoursFree 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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