Top Chicago Private Sightseeing Tours - page 3

100+ results

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing cruise with skyline views, we’ve got you covered. Cruise past iconic landmarks like the Wrigley Building on the Chicago River before heading out to Lake Michigan, where you'll take in panoramic views of the city’s world-famous skyline. With a comfortable and stylish cruiser boat, every ride is smooth, scenic, and uniquely Chicago. Want a custom experience? Choose a private boat rental with a licensed captain—ideal for birthdays, date nights, family outings, or simply relaxing with friends. You enjoy the moment, and we handle the navigation. No boating experience needed. Just bring your favorite snacks, drinks, and good vibes—we’ll provide the boat, the captain, and the unforgettable views. Book now and experience Chicago like never before—from the water!

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4.4

(7)

Chicago City Boat Tours

2 to 8 hoursFree Cancellation

from $299

Per group

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own with a private, self-guided app tour. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and more. With your GPS cuing your audio experience, this tour lets you go at your pace, style, and time, with lifetime access and no expiry.

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4.6

(5)

Chicago Millennium Park Self-Guided Walking Tour

1 to 2 hoursFree Cancellation

from $15

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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3.9

(9)

Chicago Self-Guided Audio Tour

3 to 9 hours

from $6

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

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4.7

(3)

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

from $10

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

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4.2

(6)

Chicago Riverwalk Self-Guided Walking Tour

1 to 2 hoursFree Cancellation

from $15

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.

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5.0

(1)

Chicago Highlights Private Walking Tour with a Guide

2 hoursFree Cancellation

from $131

Price varies by group size

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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5.0

(3)

Private Holiday City Tour

3 hoursFree Cancellation

from $499

Per group

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more. See the theater from Public Enemies, Harold Washington Library from Ocean’s Eleven, the Chicago Board of Trade and Calder’s Flamingo from Ferris Bueller, iconic Blues Brothers spots, and Bruce Wayne’s penthouse and Harvey Dent’s office from The Dark Knight. Perfect for film buffs and Chicago enthusiasts alike.

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4.7

(3)

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

2 hours

from $132

Price varies by group size

Chicago is renowned for its architecture—and this immersive walking tour offers the perfect way to discover its highlights. Pick from a wide range of start times, meet your private guide right in the Loop, and set off on foot. In between seeing renowned landmarks like the Chicago Cultural Center, public art by Picasso, and other heritage buildings, you’ll learn all about the city’s history.

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Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

2 hours

from $323

Price varies by group size

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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5.0

(1)

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

1 hourFree Cancellation

from $59

Per group

4.0

(10)

Chicago Art Heist: Millennium Park Puzzle Adventure

1 hour 35 minutesFree Cancellation

from $8

Price varies by group size

Likely to Sell Out

5.0

(2)

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

4 hoursFree Cancellation

from $236

It would take days to visit all of Chicago’s famous sights, but who has that kind of time? Cover the highlights of the Windy City during this private half-day walking tour. From the Magnificent Mile to Millennium Park, you’ll tick off top attractions while your guide fills you in on Chicago’s history. Finally, enjoy panoramic views overlooking the city from Hancock Tower’s Observation Deck—admission tickets included.

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5.0

(3)

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

3 hoursFree Cancellation

from $240

Price varies by group size

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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5.0

(2)

Chicago 6-Hour City Tour by Sedan

6 hoursFree Cancellation

from $960

Per group

Likely to Sell Out

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

from $869

Price varies by group size

5.0

(3)

Private Wicker Park and Bucktown Walking Tour

2 hours 30 minutesFree Cancellation

from $195

Per group

Likely to Sell Out

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago. Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

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Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

2 hours 30 minutesFree Cancellation

from $52

Price varies by group size

5.0

(2)

Custom Chicago Walking Tours

1 to 3 hoursFree Cancellation

from $20

Per group

4.6

(19)

Chicago Helicopter 25-Mile Tour for up to Three Passengers

15 minutesFree Cancellation

from $650

Per group

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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5.0

(65)

Private Chicago Food Tour with Deep Dish and Beef Sandwich

3 hoursFree Cancellation

from $225

Price varies by group size

Likely to Sell Out

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

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5.0

(27)

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

2 hoursFree Cancellation

from $508

Per group

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do European holiday customs shape winter traditions in American cities? Along State Street, seasonal décor reflects a long-standing retail heritage. The Christkindlmarket introduces a cultural tradition rooted in German history and craftsmanship. Wooden stalls and artisan goods echo centuries-old holiday markets of Europe. This experience blends festive atmosphere with cultural continuity in a refined city setting. 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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5.0

(1)

Private Christmas Walking Tour in Chicago with Christkindlmarket

2 hoursFree Cancellation

from $1,029

Price varies by group size

Likely to Sell Out

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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(6)

Private Chicago Architecture Walking Tour

3 hoursFree Cancellation

from $211

Likely to Sell Out

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

from $171

Price varies by group size

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Top Chicago Private Sightseeing Tours - page 3

100+ results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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