Chicago Private Sightseeing Tours

Discover top private sightseeing tours in Chicago, including helicopter rides, museum visits, architecture tours, and personalized city explorations for small groups.

No tours match these filters.

2 Day Private Tour Chicago to Mackinac Island Exploration

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages preva

From $2,700.00 USD

2 Hour Private Chicago Soul House Tour

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pi

★ 4.0 (5)

From $65.00 USD

2 hours Private Evening Walking Tour with the Ghosts of Chicago

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.

From $350.00 USD

4 Hours of Chicago City Tour Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

From $640.00 USD

4-Hour Chicago City Tour by SUV

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

★ 5.0 (2)

From $800.00 USD

Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’l

★ 5.0 (125)

From $215.00 USD

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

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guide

★ 5.0 (344)

From $90.10 USD

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the ne

From $9.99 USD

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour th

From $5.00 USD

Chicago 6-Hour City Tour by Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

★ 5.0 (2)

From $960.00 USD

Chicago Art Heist: Millennium Park Puzzle Adventure

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided esc

★ 4.0 (10)

From $7.40 USD

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

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 Clou

From $7.00 USD

Chicago Chinatown: Dragon Kings Puzzle Adventure

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of weather and water

★ 3.8 (10)

From $7.40 USD

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable e

★ 4.6 (38)

From $199.00 USD

Chicago Custom Private Walking Tour with A Guide ( Private Tour )

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour foc

From $129.34 USD

Chicago Downtown Private Guided Walking Tour

Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, a

From $205.00 USD

Chicago Downtown Sports History Adventure

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating

From $5.00 USD

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

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, Th

★ 4.8 (4)

From $130.50 USD

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary thea

From $263.00 USD

Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests e

From $1,800.00 USD

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

★ 2.3 (3)

From $114.05 USD

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

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 y

★ 4.8 (5)

From $9.75 USD

Chicago Highlights Private Walking Tour with a Guide

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 intim

★ 5.0 (1)

From $129.34 USD

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting mon

★ 5.0 (11)

From $45.00 USD

Chicago Jewish History Landmarks Private Guided Walking Tour

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden

From $227.00 USD

Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a c

★ 4.6 (18)

From $69.34 USD

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

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 skysc

★ 5.0 (5)

From $9.99 USD

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you lik

★ 4.6 (5)

From $14.99 USD

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

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923.

★ 5.0 (1)

From $59.00 USD

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.

★ 4.9 (207)

From $539.00 USD

Chicago Private Lakefront Sunset and Skyline Photo Tour

Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into

From $114.05 USD

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver,

From $223.41 USD

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

★ 3.0 (2)

From $114.05 USD

Chicago Private Tour

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City.

From $300.00 USD

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenie

From $1,200.00 USD

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

From $24.99 USD

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurant

★ 4.0 (8)

From $14.99 USD

Chicago Self-Guided Audio Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as y

★ 3.9 (9)

From $6.00 USD

Chicago Street Art and Creative Districts Tour

Explore Chicago’s vibrant street art and creative neighborhoods on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who

From $111.70 USD

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

Experience a global adventure without leaving Chicagoland! This tour blends rich cultural landmarks, stunning natural beauty, and nostalgic favorites, creating

★ 4.4 (7)

From $269.00 USD

Chicago Suburbs Movie Sites Private Tour

Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s D

From $270.00 USD

Chicago VIP Private Tour

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighbor

From $499.00 USD

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holid

★ 4.9 (81)

From $84.99 USD

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 pea

From $9.75 USD

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangster

From $6.99 USD

Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of

★ 3.5 (2)

From $5.00 USD

Custom Chicago Walking Tours

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explo

★ 5.0 (4)

From $75.00 USD

Discover Chicago: A Self-Guided Walking Tour

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant c

★ 2.0 (1)

From $3.52 USD

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at ev

★ 5.0 (2)

From $99.00 USD

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your

From $195.00 USD

Downtown Chicago City Tour in a Super Car [30 Minute Experience]

Turn heads and take in the views with your Premier Chicago Tour Experience! Your journey begins in the passenger seat of an automotive masterpiece. Tour downt

From $160.00 USD

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 t

From $27.00 USD

Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

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 Ch

From $55.00 USD

Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s

★ 5.0 (2)

From $75.00 USD

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real mummies,

★ 4.0 (3)

From $313.00 USD

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

★ 4.3 (8)

From $223.41 USD

Guided Audio Road Trip Route 66

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies

★ 1.0 (1)

From $29.40 USD

Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's most haunted

★ 4.0 (6)

From $6.57 USD

Historic Pullman Private Half-Day Walking Tour

Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once

From $223.00 USD

Hyde Park Walking Tour History Race and Urban Change

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat

From $5.00 USD

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility impairm

★ 5.0 (1)

From $125.00 USD

Lincoln Park Zoo & Nature Museum Private Tour

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

★ 5.0 (21)

From $274.98 USD

Logan Square Walking Tour Experience

An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chica

From $35.00 USD

Luxury SUV 4 Hour Sightseeing Tour

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

★ 4.0 (1)

From $350.00 USD

Mackinac Island Private Day Tour from Chicago

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embrace

From $1,350.00 USD

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, an

From $17.04 USD

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 loca

★ 5.0 (5)

From $35.00 USD

Private & All-Inclusive Chicago Downtown Highlights Walking Tour

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions! The day will begin with you meeting with yo

From $223.00 USD

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a priv

From $319.24 USD

Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the c

★ 4.8 (134)

From $849.00 USD

Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in a sp

★ 5.0 (1)

From $750.00 USD

Private Architectural Walking Tour in Chicago Cultural Center

This private architectural walking tour in Chicago reveals a city shaped by cultural ambition and design excellence. You will begin at the historic Cultural Cen

From $869.00 USD

Private Architectural Walking Tour in Chicago Historic Residences

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where ea

From $869.00 USD

Private Architectural Walking Tour in Chicago Loop Landmarks

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture

From $869.00 USD

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 th

★ 4.8 (6)

From $211.00 USD

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on

★ 5.0 (1)

From $999.00 USD

Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city'

★ 5.0 (87)

From $224.99 USD

Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, G

★ 5.0 (6)

From $288.00 USD

Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most

★ 5.0 (5)

From $785.27 USD

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life

★ 5.0 (27)

From $162.50 USD

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic sky

★ 5.0 (13)

From $180.00 USD

Private Chicago Street Food Walking Tour With A Local Guide

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary lan

From $304.54 USD

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where archite

★ 5.0 (1)

From $1,029.00 USD

Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chi

★ 5.0 (3)

From $770.00 USD

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public a

From $869.00 USD

Private Family Walking Tour in Chicago Loop Cultural District

This private family walking tour in Chicago introduces the cultural and architectural identity of the Loop district. You will begin in the financial center, whe

From $669.00 USD

Private Historical Ghost Walking Tour in Chicago Lincoln Park

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by

From $869.00 USD

Private History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walking among gigantic towers of downtown, we will learn why and ho

From $144.00 USD

Private Holiday City Tour

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! Enjo

★ 5.0 (3)

From $499.00 USD

Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. From

★ 4.9 (81)

From $160.00 USD

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed capt

★ 5.0 (73)

From $507.96 USD

Private Shopping Tour from Chicago to Chicago Premium Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and

From $291.60 USD

Private Shopping Tour from Chicago to Fashion Outlets of Chicago

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes

From $264.56 USD

Private Shopping Tour from Chicago to Lighthouse Place Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from cl

From $370.38 USD

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the

From $1,058.24 USD

Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a

★ 5.0 (3)

From $195.00 USD

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’

From $14.99 USD

Route 66 Multi Day Tour from Chicago to Los Angeles

Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Ex

From $10.00 USD

Routes POR Route 66 with Audio Guide

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, T

From $56.44 USD

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, gorg

★ 3.3 (3)

From $6.46 USD

Sip Happens: Chicago Loop Prohibition Tour

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars a

★ 1.0 (1)

From $5.00 USD

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

Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive into a treasure trove of art

From $318.00 USD

Skyline Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who sha

★ 5.0 (1)

From $169.32 USD

The Bear Private Pedicab Food Tour of Chicago

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

★ 5.0 (1)

From $200.00 USD

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

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hanco

★ 5.0 (3)

From $240.00 USD

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, som

★ 5.0 (2)

From $236.00 USD