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Top 10 Best Chicago Private Sightseeing Tours

Found 86 Private Sightseeing Tours activities in Chicago. Sort by Popularity.
 

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

(5 of 269 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 $90.01
 
Private Art Institute of Chicago Skip-the-Line Guided Tour

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

  • Chicago
  • Superb269 reviews5

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

    Free Cancellation
    Private Tour
    Start From $90.01
 
 

Chicago City Tours

(4.8 of 16 reviews)

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 experience, customizable from 2 to 8 hours. From the iconic skyline to ... More

Free Cancellation
Private Tour
Start From $199.00
 
Chicago City Tours

Chicago City Tours

  • Chicago
  • Superb16 reviews4.8

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, m....

    Free Cancellation
    Private Tour
    Start From $199.00
 
 

Private Chicago Foodie Tour

(5 of 6 reviews)

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, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city la... More

Free Cancellation
Private Tour
Start From $288.00
 
Private Chicago Foodie Tour Likely to Sell Out

Private Chicago Foodie Tour

  • Chicago
  • Superb6 reviews5

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites lik....

    Free Cancellation
    Private Tour
    Start From $288.00
 
 

Art Institute of Chicago Private Expert Guided Tour

(5 of 81 reviews)

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’ll discover an extraordinary collection spanning centuries and cultur... More

Free Cancellation
Private Tour
Start From $215.00
 
Art Institute of Chicago Private Expert Guided Tour Likely to Sell Out

Art Institute of Chicago Private Expert Guided Tour

  • Chicago
  • Superb81 reviews5

Let our expert local guides share their passion with you for The Art Institute of Chicago on this pr....

    Free Cancellation
    Private Tour
    Start From $215.00
 
 

Haunted Chicago Exploration Game and Tour

(3.8 of 5 reviews)

Discover Chicago’s haunted locations by following clues and solving puzzles on your phone. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Ready for an adventure... More

Free Cancellation
Private Tour
Start From $7.09
 
Haunted Chicago Exploration Game and Tour Likely to Sell Out

Haunted Chicago Exploration Game and Tour

  • Chicago
  • Very Good5 reviews3.8

Discover Chicago’s haunted locations by following clues and solving puzzles on your phone. As you ....

    Free Cancellation
    Private Tour
    Start From $7.09
 
 

Chicago Millennium Park Self-Guided Walking Tour

(4.6 of 5 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 Likely to Sell Out

Chicago Millennium Park Self-Guided Walking Tour

  • Chicago
  • Superb5 reviews4.6

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 Self-Guided Audio Tour

(3.9 of 9 reviews)

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... More

Free Cancellation
Private Tour
Start From $9.00
 
Chicago Self-Guided Audio Tour Likely to Sell Out

Chicago Self-Guided Audio Tour

  • Chicago
  • Very Good9 reviews3.9

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at....

    Free Cancellation
    Private Tour
    Start From $9.00
 
 

Chicago Riverwalk Self-Guided Walking Tour

(4.2 of 6 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 Likely to Sell Out

Chicago Riverwalk Self-Guided Walking Tour

  • Chicago
  • Exellent6 reviews4.2

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

    Free Cancellation
    Private Tour
    Start From $14.99
 
 

Private 45-Minute Chicago Skyline Helicopter Tour

(4.8 of 126 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 Likely to Sell Out

Private 45-Minute Chicago Skyline Helicopter Tour

  • Chicago
  • Superb126 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
 
 

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

(5 of 27 reviews)

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 captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

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

  • Chicago
  • Superb27 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Chicago Lakefront Electric Bike Tour

(4.5 of 16 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 Likely to Sell Out

Chicago Lakefront Electric Bike Tour

  • Chicago
  • Exellent16 reviews4.5

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
 
 

2 Hour Private Chicago Soul House Tour

(3.3 of 3 reviews)

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 pictures and have great conversation! The personal, small tour approach ... More

Free Cancellation
Private Tour
Start From $65.00
 
2 Hour Private Chicago Soul House Tour Likely to Sell Out

2 Hour Private Chicago Soul House Tour

  • Chicago
  • Good3 reviews3.3

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personali....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Eastside Chicago The Heist Exploration Game and Tour

(4 of 10 reviews)

The city sparkles with steel, glass and stolen art. You’ve just pulled off the heist of a lifetime, walking the streets of Chicago with Edward Hopper’s Nighthawks tucked in your bag. Now all you need is to disappear into the c... More

Free Cancellation
Private Tour
Start From $7.09
 
Eastside Chicago The Heist Exploration Game and Tour Likely to Sell Out

Eastside Chicago The Heist Exploration Game and Tour

  • Chicago
  • Very Good10 reviews4

The city sparkles with steel, glass and stolen art. You’ve just pulled off the heist of a lifetime....

    Free Cancellation
    Private Tour
    Start From $7.09
 
 

Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

(4 of 10 reviews)

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Q... More

Free Cancellation
Private Tour
Start From $9.75
 
Chicago’s Millennium Park Self Guided Audio GPS Walking Tour Likely to Sell Out

Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

  • Chicago
  • Very Good10 reviews4

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. Weâ€....

    Free Cancellation
    Private Tour
    Start From $9.75
 
 

Chicago Haunted Ghost Tour GPS Self-Guided 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 $9.75
 
Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour Likely to Sell Out

Chicago Haunted Ghost Tour GPS Self-Guided 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 $9.75
 
 

Chicago Private Custom City Tour with Hotel Pick Up

(4.9 of 201 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 Likely to Sell Out

Chicago Private Custom City Tour with Hotel Pick Up

  • Chicago
  • Superb201 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
 
 

Chicago Helicopter 25-Mile Tour for up to Three Passengers

(4.3 of 11 reviews)

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks,... More

Free Cancellation
Private Tour
Start From $650.00
 
Chicago Helicopter 25-Mile Tour for up to Three Passengers Likely to Sell Out

Chicago Helicopter 25-Mile Tour for up to Three Passengers

  • Chicago
  • Exellent11 reviews4.3

A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. Fr....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

Chicago Highlights Private Walking Tour with a Guide

(5 of 1 review)

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 $130.14
 
Chicago Highlights Private Walking Tour with a Guide Likely to Sell Out

Chicago Highlights Private Walking Tour with a Guide

  • Chicago
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $130.14
 
 

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

(5 of 3 reviews)

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 you... More

Free Cancellation
Private Tour
Start From $9.99
 
Self-Guided Chicago Loop Tour Explore the City at Your Own Pace Likely to Sell Out

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

  • Chicago
  • Superb3 reviews5

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s histo....

    Free Cancellation
    Private Tour
    Start From $9.99
 
 

Private Holiday City Tour

(5 of 1 review)

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... More

Free Cancellation
Private Tour
Start From $499.00
 
Private Holiday City Tour Likely to Sell Out

Private Holiday City Tour

  • Chicago
  • Superb1 review5

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in....

    Free Cancellation
    Private Tour
    Start From $499.00
 
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