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Top 10 Best Chicago Private Sightseeing Tours

Found 80 Private Sightseeing Tours activities in Chicago. Sort by Popularity. - Page 3
 

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

(3.5 of 2 reviews)

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 private tour and discover the hidden architectural treasures of Chicago wi... More

Free Cancellation
Private Tour
Start From $225.88
 
Private 2-Hour Walking Tour: Chicago Loop Interior Architecture Likely to Sell Out

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

  • Chicago
  • Good2 reviews3.5

Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago d....

    Free Cancellation
    Private Tour
    Start From $225.88
 
 

Private Frida and Friends Tour in Pilsen

(4.3 of 6 reviews)

Discover Pilsen and its local art, street art, food and people. We will visit a traditional bakery and taqueria and enjoy the art of many great local artists. And then there are the hundreds of cool murals in the neighborhood. We... More

Free Cancellation
Private Tour
Start From $240.00
 
Private Frida and Friends Tour in Pilsen Likely to Sell Out

Private Frida and Friends Tour in Pilsen

  • Chicago
  • Exellent6 reviews4.3

Discover Pilsen and its local art, street art, food and people. We will visit a traditional bakery ....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Love is in the Windy City - Chicago Walking Tour

(4.3 of 6 reviews)

How about an unforgettable time in Chicago with your beloved? If you're looking to have the most romantic time while visiting famous attractions of Chicago, then you can't miss this walking tour! Why is Chicago called "The Windy C... More

Free Cancellation
Private Tour
Start From $329.36
 
Love is in the Windy City - Chicago Walking Tour Likely to Sell Out

Love is in the Windy City - Chicago Walking Tour

  • Chicago
  • Exellent6 reviews4.3

How about an unforgettable time in Chicago with your beloved? If you're looking to have the most rom....

    Free Cancellation
    Private Tour
    Start From $329.36
 
 

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 Likely to Sell Out

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
 
 

Private Holiday City Tour

(4 of 5 reviews)

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
  • Very Good5 reviews4

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
 
 

Chicago Private Walking Food Tour With Secret Food Tours

(5 of 43 reviews)

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's biggest food hits, many dishes with roots dating back over 150 years... More

Free Cancellation
Private Tour
Start From $306.00
 
Chicago Private Walking Food Tour With Secret Food Tours Likely to Sell Out

Chicago Private Walking Food Tour With Secret Food Tours

  • Chicago
  • Superb43 reviews5

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the ....

    Free Cancellation
    Private Tour
    Start From $306.00
 
 

Walking Tour of Chicago’s Artsy Cultural Landmarks

(5 of 43 reviews)

Dive into "Chicago's Artsy Cultural Landmarks – Walking Tour," a vibrant exploration of the city's iconic artistic and architectural gems. Start at the Chicago Cultural Center, home to the world's largest Tiffany stained-glass d... More

Free Cancellation
Private Tour
Start From $329.36
 
Walking Tour of Chicago’s Artsy Cultural Landmarks Likely to Sell Out

Walking Tour of Chicago’s Artsy Cultural Landmarks

  • Chicago
  • Superb43 reviews5

Dive into "Chicago's Artsy Cultural Landmarks – Walking Tour," a vibrant exploration of the city's....

    Free Cancellation
    Private Tour
    Start From $329.36
 
 

Private Chicago TV and Movie Locations 3 Hour Walking Tour

(5 of 1 review)

Whether you’re a movie fanatic or simply want to take a Chicago sightseeing tour that hits iconic landmarks, this walking tour is for you! We’ll start our tour in the Chicago Loop, a lively neighborhood filled with incredible... More

Free Cancellation
Private Tour
Start From $320.00
 
Private Chicago TV and Movie Locations 3 Hour Walking Tour Likely to Sell Out

Private Chicago TV and Movie Locations 3 Hour Walking Tour

  • Chicago
  • Superb1 review5

Whether you’re a movie fanatic or simply want to take a Chicago sightseeing tour that hits iconic ....

    Free Cancellation
    Private Tour
    Start From $320.00
 
 

Wind City Wanderlust: A Chicago Family Odyssey

(5 of 1 review)

Embark on a family adventure starting at the iconic metal horse sculpture at 425 S. Financial Place, a symbol of strength in the city's bustling financial district. Wander to the Chicago Board of Trade Building, marveling at its s... More

Free Cancellation
Private Tour
Start From $195.83
 
Wind City Wanderlust: A Chicago Family Odyssey Likely to Sell Out

Wind City Wanderlust: A Chicago Family Odyssey

  • Chicago
  • Superb1 review5

Embark on a family adventure starting at the iconic metal horse sculpture at 425 S. Financial Place,....

    Free Cancellation
    Private Tour
    Start From $195.83
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $5.77
(Saving 20% ) $7.22
 
-20% Gangster Story Quest Experience in Chicago Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $5.77
    (Saving 20% ) $7.22
 
 

Art of a City Downtown Chicago - Exclusive Guided Walking Tour

(3 of 2 reviews)

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 ... More

Free Cancellation
Private Tour
Start From $51.94
 
Art of a City Downtown Chicago - Exclusive Guided Walking Tour Likely to Sell Out

Art of a City Downtown Chicago - Exclusive Guided Walking Tour

  • Chicago

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hid....

    Free Cancellation
    Private Tour
    Start From $51.94
 
 

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

(5 of 2 reviews)

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, some amazing architecture, & a ton of great photos then this is the tour ... More

Free Cancellation
Private Tour
Start From $236.00
 
️ Chicago Instagram Walking Tour (Private & All- Inclusive) Likely to Sell Out

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

  • Chicago
  • Superb2 reviews5

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in ....

    Free Cancellation
    Private Tour
    Start From $236.00
 
 

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 $132.00
 
Private Downtown Chicago TV and Movie Sites Guided Walking Tour Likely to Sell Out

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 $132.00
 
 

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 $9.75
 
Chicago's Dark Side Self-Guided Smartphone Walking Tour Likely to Sell Out

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 $9.75
 
 

The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour

(4.7 of 3 reviews)

Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour. • Take in Chicago’s concrete giants and hear fascinating stories about quirky artworks, local ... More

Free Cancellation
Private Tour
Start From $11.99
 
The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour Likely to Sell Out

The Loop, River North and Chicago’s Theater District: A Self-Gu....

  • Chicago
  • Superb3 reviews4.7

Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with....

    Free Cancellation
    Private Tour
    Start From $11.99
 
 

Chicago Lincoln Square Quest Experience

(4.7 of 3 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

Special Offer
Free Cancellation
Private Tour
Start From $8.89
(Saving 20% ) $11.12
 
-20% Chicago Lincoln Square Quest Experience Likely to Sell Out

Chicago Lincoln Square Quest Experience

  • Chicago
  • Superb3 reviews4.7

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $8.89
    (Saving 20% ) $11.12
 
 

A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

(3.5 of 2 reviews)

This self-guided audio tour begins at the Laboratory Schools founded by John Dewey, and winds through the University of Chicago. Along the way, walkers will encounter world-renowned architects and Nobel Laureates, robber barons an... More

Free Cancellation
Private Tour
Start From $5.40
 
A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers Likely to Sell Out

A Storied Neighborhood: A Self-Guided Audio Tour with Bill Ayers

  • Chicago
  • Good2 reviews3.5

This self-guided audio tour begins at the Laboratory Schools founded by John Dewey, and winds throug....

    Free Cancellation
    Private Tour
    Start From $5.40
 
 

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

(3.5 of 2 reviews)

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 gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians w... More

Free Cancellation
Private Tour
Start From $7.99
 
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour Likely to Sell Out

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

  • Chicago
  • Good2 reviews3.5

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affor....

    Free Cancellation
    Private Tour
    Start From $7.99
 
 

Chicago Highlights Private Walking Tour with a Guide

(3.5 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 $122.40
 
Chicago Highlights Private Walking Tour with a Guide Likely to Sell Out

Chicago Highlights Private Walking Tour with a Guide

  • Chicago
  • Good2 reviews3.5

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

    Free Cancellation
    Private Tour
    Start From $122.40
 
 

Echoes of Elegance: Chicago’s Architectural Splendors

(3.5 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 $262.60
 
Echoes of Elegance: Chicago’s Architectural Splendors Likely to Sell Out

Echoes of Elegance: Chicago’s Architectural Splendors

  • Chicago
  • Good2 reviews3.5

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

    Free Cancellation
    Private Tour
    Start From $262.60
 
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