Top Chicago Private Sightseeing Tours

100+ results

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

Chicago City Private Tours

2 to 8 hoursFree Cancellation

4.7

(28)

from $199

Per group

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

(3,195)

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

(16,085)

from $39

Chicago River 90-Minute Architecture Tour

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

(10,004)

from $45

Personalized Private Driving Tour of Chicago for 1-3 People

Looking for a convenient way to see Chicago rain or shine? Discover Chicago and its remarkable landmarks in a unique way with a private tour designed just for you. Enjoy the comfort of a private car as a friendly local guide takes you through the city’s iconic architecture, vibrant neighborhoods, and scenic drives. This tour allows you to explore at your own pace while receiving insider tips and local insights. - Private tour for 1-3 people with a local guide - Explore iconic landmarks and vibrant neighborhoods - Flexible itinerary tailored to your interests - Enjoy the comfort of a private car with scenic drives

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Personalized Private Driving Tour of Chicago for 1-3 People

from $395

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

(295)

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

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

(1,239)

from $30

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

4.4

(910)

from $33

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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Chicago Private Boat Tours

2 to 8 hoursFree Cancellation

4.4

(7)

from $299

Per group

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

Likely to Sell Out

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(2,333)

from $45

Chicago Gangsters and Prohibition Private History Tour

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

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Chicago Gangsters and Prohibition Private History Tour

2 hoursFree Cancellation

2.3

(3)

from $115

Price varies by group size

Private Frida and Friends Tour in Pilsen

2 hoursFree Cancellation

4.3

(6)

from $240

Per group

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

(1,829)

from $44

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

4.6

(520)

from $29

Likely to Sell Out

It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.

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Private Chicago Foodie Tour

4 hoursFree Cancellation

5.0

(6)

from $288

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

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Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

3.9

(2,243)

from $49

Special Offer

Private Chicago Guided Tour with Hotel Pickup

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.

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Private Chicago Guided Tour with Hotel Pickup

4 hoursFree Cancellation

Price varies by group size

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

4.5

from $25

Likely to Sell Out

Private Chicago History Museum Tour

2 hoursFree Cancellation

5.0

(18)

from $163

Price varies by group size

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

Special Offer

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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Top Attractions in Chicago

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Top Chicago Private Sightseeing Tours

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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