Top Chicago Private Sightseeing Tours

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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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Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

2 hours to 2 hours 30 minutesFree Cancellation

Member Pricing

Stroll through Chicago's winter streets, lit up for the holidays, without the hassle of navigating the city yourself on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk.

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Chicago-Style Holiday Hike: Festive Food and Walking Tour

3 hoursFree Cancellation

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

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 -BOOKING: Please note the tour guide will contact you to schedule an exact time for your tour after you have completed the booking. There is no option to pick a start time.

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Pilsen Chicago Walking Tour: Street Art & Mexican History

1 hour 15 minutesFree Cancellation

Member Pricing

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

Member Pricing

Private Chicago History Museum Tour

2 hoursFree Cancellation

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

(388)

from $63

Special Offer

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.

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Chicago Private Night Skyline and Lakefront Scenic Tour

2 hoursFree Cancellation

Price varies by group size

Member Pricing

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

5% savings

from

$35$33

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

Special Offer

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

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Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

1 to 2 hoursFree Cancellation

Member Pricing

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects modern civic expression. What defines Chicago’s identity as a center of American innovation? Cloud Gate offers a striking reflection of skyline and sky. The DuSable Bridge stands as an engineering achievement tied to the city’s growth. Along the waterfront, Navy Pier reveals Chicago’s connection to commerce and recreation. This route connects cultural landmarks with the story of a city shaped by industry and design. 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 Cultural Walking Tour in Chicago with Lakefront Landmarks

2 hoursFree Cancellation

5% savings

from

$869$826

Price varies by group size

Member Pricing

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

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

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

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

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

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

1 to 30 days

4.0

(370)

from $84

Member Pricing

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.

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Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

1 to 2 hoursFree Cancellation

5% savings

from

$16$16

Price varies by group size

Member Pricing

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

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

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

Chicago Lakefront Trail: A Self-Guided Bike Tour

This self-guided bike tour traces Chicago's reinvention from the ashes of the Great Fire to the skyline that rose in its place, pedaling the Lakefront Trail with Lake Michigan on one side and the city's icons on the other. The route begins near Navy Pier and rolls through Museum Campus, past the Shedd Aquarium, Adler Planetarium, and Field Museum. Buckingham Fountain and the towering Willis Tower come next, followed by Millennium Park's Cloud Gate — Chicago's beloved "Bean." A quick pass through the Loop takes in the Chicago Theatre, State Street, and Union Station before crossing the Chicago River. Stories of the Great Fire and the innovators who rebuilt the city play through your headphones the whole way. Perfect for first-time visitors, casual cyclists, and anyone craving a fresh angle on the city. Download the VoiceMap app and enter the ticket code from your confirmation email to start riding.

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Chicago Lakefront Trail: A Self-Guided Bike Tour

1 to 2 hoursFree Cancellation

5% savings

from

$15$14

Member Pricing

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

Price varies by group size

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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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