Menu

Top 10 Best Chicago Private Sightseeing Tours

Found 83 Private Sightseeing Tours activities in Chicago. Sort by Popularity.
 

Private 45-Minute Chicago Skyline Helicopter Tour

(4.8 of 119 reviews)

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 city of Chicago on a 45 minute thrill seeking guided tour. The price is... More

Free Cancellation
Private Tour
Start From $849.00
 
Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

  • Chicago
  • Superb119 reviews4.8

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3....

    Free Cancellation
    Private Tour
    Start From $849.00
 
 

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

(4.8 of 119 reviews)

Get to know the city through the eyes of a local guide. With no set itinerary, you can customize the tour or leave it to the local for an enlightening introduction to the city. With our private walking tours, you'll skip the munda... More

Free Cancellation
Private Tour
Start From $116.78
 
Chicago Custom Private Walking Tour with A Guide ( Private Tour )

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

  • Chicago
  • Superb119 reviews4.8

Get to know the city through the eyes of a local guide. With no set itinerary, you can customize the....

    Free Cancellation
    Private Tour
    Start From $116.78
 
 

Chicago Private Tour

(4.8 of 119 reviews)

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. Be satisfied that you experienced the most important and beautiful si... More

Free Cancellation
Private Tour
Start From $300.00
 
Chicago Private Tour

Chicago Private Tour

  • Chicago
  • Superb119 reviews4.8

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and vis....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Private Al Capone Gangster Tour in Chicago

(4.7 of 12 reviews)

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: ... More

Free Cancellation
Private Tour
Start From $880.00
 
Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

  • Chicago
  • Superb12 reviews4.7

Chicago and the history of the mob are synonymous when we look back at history. That’s why we prov....

    Free Cancellation
    Private Tour
    Start From $880.00
 
 

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

(5 of 185 reviews)

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 guided museum tour, you’ll be able to skip the line and explore it’s mo... More

Free Cancellation
Private Tour
Start From $132.50
 
Art Institute of Chicago Skip-the-Line Guided Museum Tour

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

  • Chicago
  • Superb185 reviews5

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Me....

    Free Cancellation
    Private Tour
    Start From $132.50
 
 

Private Chicago Scenic Driving Tour

(5 of 6 reviews)

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour wi... More

Free Cancellation
Private Tour
Start From $315.00
 
 Private Chicago Scenic Driving Tour

Private Chicago Scenic Driving Tour

  • Chicago
  • Superb6 reviews5

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires ....

    Free Cancellation
    Private Tour
    Start From $315.00
 
 

Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

(3.3 of 7 reviews)

This is a drive by tour, no tour guide included, admission not included. Choose the number of hours & the vehicle type and we can help you schedule it. The list has been build with efficiency in mind and all stops are arranged in... More

Free Cancellation
Private Tour
Start From $300.00
 
Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle

  • Chicago
  • Good7 reviews3.3

This is a drive by tour, no tour guide included, admission not included. Choose the number of hours....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Insta Walk and Polaroid Photoshoot in Chicago

(3.3 of 7 reviews)

Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative ideas during our relaxed and friendly stroll. I'll use both iPhone and Polaroid cameras to capture your best shots. You'll get abou... More

Free Cancellation
Private Tour
Start From $99.00
 
 Insta Walk and Polaroid Photoshoot in Chicago

Insta Walk and Polaroid Photoshoot in Chicago

  • Chicago
  • Good7 reviews3.3

Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative id....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Chicago Private Custom City Tour with Hotel Pick Up

(4.9 of 189 reviews)

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.  Our services include pick up from your downtown Chicago hotel, a 3-4... More

Free Cancellation
Private Tour
Start From $539.00
 
Chicago Private Custom City Tour with Hotel Pick Up

Chicago Private Custom City Tour with Hotel Pick Up

  • Chicago
  • Superb189 reviews4.9

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Privat....

    Free Cancellation
    Private Tour
    Start From $539.00
 
 

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

(4.5 of 2 reviews)

Featuring over 30 locations! Take this two-hour walking tour in downtown Chicago and visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more! Visit the infamous theater venue from Public... More

Free Cancellation
Private Tour
Start From $81.25
 
Private Downtown Chicago TV and Movie Sites Guided Walking Tour

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

  • Chicago
  • Exellent2 reviews4.5

Featuring over 30 locations! Take this two-hour walking tour in downtown Chicago and visit sites fro....

    Free Cancellation
    Private Tour
    Start From $81.25
 
 

Eastside Chicago The Heist Exploration Game and Tour

(3.9 of 9 reviews)

Play a city game where you will follow clues to discover amazing places and local stories in Chicago. You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to r... More

Free Cancellation
Private Tour
Start From $6.89
 
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

  • Chicago
  • Very Good9 reviews3.9

Play a city game where you will follow clues to discover amazing places and local stories in Chicago....

    Free Cancellation
    Private Tour
    Start From $6.89
 
 

Chicago Lakefront Electric Bike Tour

(4.3 of 12 reviews)

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 chance to ride Electric Bikes and see the city from a different vantage... More

Free Cancellation
Private Tour
Start From $69.34
 
Chicago Lakefront Electric Bike Tour

Chicago Lakefront Electric Bike Tour

  • Chicago
  • Exellent12 reviews4.3

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful ....

    Free Cancellation
    Private Tour
    Start From $69.34
 
 

Dragon Kings Quest Experience in Chinatown Chicago

(3.8 of 5 reviews)

Get ready to explore Chicago Chinatown landmarks, hotspots, and popular restaurants all while playing the role of a brave Imperial Advisor to the Emperor of China. As you solve challenges, the story unfolds and exact directions ... More

Free Cancellation
Private Tour
Start From $6.89
 
Dragon Kings Quest Experience in Chinatown Chicago

Dragon Kings Quest Experience in Chinatown Chicago

  • Chicago
  • Very Good5 reviews3.8

Get ready to explore Chicago Chinatown landmarks, hotspots, and popular restaurants all while playin....

    Free Cancellation
    Private Tour
    Start From $6.89
 
 

Chicago Riverwalk Self-Guided Walking Tour

(4 of 5 reviews)

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax, boat rentals, an... More

Free Cancellation
Private Tour
Start From $14.99
 
Chicago Riverwalk Self-Guided Walking Tour

Chicago Riverwalk Self-Guided Walking Tour

  • Chicago
  • Very Good5 reviews4

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called....

    Free Cancellation
    Private Tour
    Start From $14.99
 
 

Chicago Lincoln Square Quest Experience

(4 of 5 reviews)

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... More

Free Cancellation
Private Tour
Start From $6.89
 
Chicago Lincoln Square Quest Experience

Chicago Lincoln Square Quest Experience

  • Chicago
  • Very Good5 reviews4

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores....

    Free Cancellation
    Private Tour
    Start From $6.89
 
 

Chicago Millennium Park Self-Guided Walking Tour

(4.5 of 4 reviews)

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 like; pausing to explore further on your own. Take in the sights of the p... More

Free Cancellation
Private Tour
Start From $14.99
 
Chicago Millennium Park Self-Guided Walking Tour

Chicago Millennium Park Self-Guided Walking Tour

  • Chicago
  • Exellent4 reviews4.5

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and y....

    Free Cancellation
    Private Tour
    Start From $14.99
 
 

Chicago's Dark Side Self-Guided Smartphone Walking Tour

(4.7 of 3 reviews)

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 music... More

Free Cancellation
Private Tour
Start From $6.95
 
Chicago's Dark Side Self-Guided Smartphone Walking Tour

Chicago's Dark Side Self-Guided Smartphone Walking Tour

  • Chicago
  • Superb3 reviews4.7

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like a....

    Free Cancellation
    Private Tour
    Start From $6.95
 
 

Gangster Story Quest Experience in Chicago

(3 of 2 reviews)

A historic walk that tells the story of Chicago's emergence from the ashes of the Great Chicago Fire. Your stroll takes you from the heart of downtown north across the river. You'll see world-famous landmarks while learning answer... More

Free Cancellation
Private Tour
Start From $6.89
 
Gangster Story Quest Experience in Chicago

Gangster Story Quest Experience in Chicago

  • Chicago

A historic walk that tells the story of Chicago's emergence from the ashes of the Great Chicago Fire....

    Free Cancellation
    Private Tour
    Start From $6.89
 
 

Chicago Highlights Private Walking Tour with a Guide

(3 of 2 reviews)

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, foll... More

Free Cancellation
Private Tour
Start From $116.78
 
Chicago Highlights Private Walking Tour with a Guide

Chicago Highlights Private Walking Tour with a Guide

  • Chicago

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the ....

    Free Cancellation
    Private Tour
    Start From $116.78
 
 

Echoes of Elegance: Chicago’s Architectural Splendors

(3 of 2 reviews)

Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultural allure. From the soaring heights of 1150 Lake Shore Drive... More

Free Cancellation
Private Tour
Start From $244.18
 
Echoes of Elegance: Chicago’s Architectural Splendors Likely to Sell Out

Echoes of Elegance: Chicago’s Architectural Splendors

  • Chicago

Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tell....

    Free Cancellation
    Private Tour
    Start From $244.18
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com