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Top 10 Best Chicago Private Sightseeing Tours

Found 86 Private Sightseeing Tours activities in Chicago. Sort by Popularity. - Page 3
 

Private Frida and Friends Tour in Pilsen

(4.3 of 6 reviews)

Step into one of Chicago’s most colorful and creative neighborhoods — Pilsen — and experience its vibrant blend of art, culture, and community. This private guided walking tour takes you through streets filled with powerful ... More

Free Cancellation
Private Tour
Start From $240.00
 
Private Frida and Friends Tour in Pilsen

Private Frida and Friends Tour in Pilsen

  • Chicago
  • Exellent6 reviews4.3

Step into one of Chicago’s most colorful and creative neighborhoods — Pilsen — and experience ....

    Free Cancellation
    Private Tour
    Start From $240.00
 
 

Romantic Chicago Walking Tour: Love Stories & Landmarks

(4.3 of 6 reviews)

Skip the crowds this is a private tour for your group only! 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'... More

Free Cancellation
Private Tour
Start From $656.64
 
Romantic Chicago Walking Tour: Love Stories & Landmarks Likely to Sell Out

Romantic Chicago Walking Tour: Love Stories & Landmarks

  • Chicago
  • Exellent6 reviews4.3

Skip the crowds this is a private tour for your group only! How about an unforgettable time in Chica....

    Free Cancellation
    Private Tour
    Start From $656.64
 
 

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

(4.3 of 6 reviews)

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... More

Free Cancellation
Private Tour
Start From $24.99
 
Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle Likely to Sell Out

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

  • Chicago
  • Exellent6 reviews4.3

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Mill....

    Free Cancellation
    Private Tour
    Start From $24.99
 
 

Chicago Gangsters: Self-Guided Crime Story Puzzle Walk

(2.3 of 3 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 $5.90
 
Chicago Gangsters: Self-Guided Crime Story Puzzle Walk Likely to Sell Out

Chicago Gangsters: Self-Guided Crime Story Puzzle Walk

  • 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 $5.90
 
 

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

(4.5 of 2 reviews)

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, The Dark Knight, The Bear, and more. See the theater from Public Enemi... 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

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Vis....

    Free Cancellation
    Private Tour
    Start From $132.00
 
 

Private Wicker Park and Bucktown Walking Tour

(5 of 2 reviews)

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 whole different side of the city. The tour has 2 options: Wicker Pa... More

Free Cancellation
Private Tour
Start From $195.00
 
Private Wicker Park and Bucktown Walking Tour Likely to Sell Out

Private Wicker Park and Bucktown Walking Tour

  • Chicago
  • Superb2 reviews5

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeab....

    Free Cancellation
    Private Tour
    Start From $195.00
 
 

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

(5 of 1 review)

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 $8.86
 
Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago Likely to Sell Out

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

  • Chicago
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $8.86
 
 

Exclusive Private Art Walking Tour in Chicago

(5 of 1 review)

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
 
Exclusive Private Art Walking Tour in Chicago Likely to Sell Out

Exclusive Private Art Walking Tour in Chicago

  • Chicago
  • Superb1 review5

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
 
 

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

(5 of 2 reviews)

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, and complete challenges for a unique experience blending sightseeing wit... More

Free Cancellation
Private Tour
Start From $17.14
 
Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game Likely to Sell Out

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

  • Chicago
  • Superb2 reviews5

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic lan....

    Free Cancellation
    Private Tour
    Start From $17.14
 
 

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

(1 of 1 review)

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 $14.99
 
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

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 $14.99
 
 

Personalized Private Chicago Tour for 2-3 People

(5 of 1 review)

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 tak... More

Special Offer
Free Cancellation
Private Tour
Start From $316.00
(Saving 20% ) $395.00
 
-20% Personalized Private Chicago Tour for 2-3 People Likely to Sell Out

Personalized Private Chicago Tour for 2-3 People

  • Chicago
  • Superb1 review5

Looking for a convenient way to see Chicago rain or shine? Discover Chicago and its remarkable lan....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $316.00
    (Saving 20% ) $395.00
 
 

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

(2.8 of 4 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

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

(5 of 1 review)

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. You are a detective in Chicago and a woman has been found murdered... More

Free Cancellation
Private Tour
Start From $22.73
 
Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit Likely to Sell Out

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

  • Chicago
  • Superb1 review5

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “....

    Free Cancellation
    Private Tour
    Start From $22.73
 
 

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

(5 of 1 review)

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 $9.99
 
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
  • Superb1 review5

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 $9.99
 
 

Custom Chicago Walking Tours

(5 of 2 reviews)

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s ... More

Free Cancellation
Private Tour
Start From $20.00
 
Custom Chicago Walking Tours Likely to Sell Out

Custom Chicago Walking Tours

  • Chicago
  • Superb2 reviews5

We create custom walking tours for groups of all sizes and interests, blending delicious food experi....

    Free Cancellation
    Private Tour
    Start From $20.00
 
 

Lincoln Park Spirits Ghost Private Walking Tour

(5 of 2 reviews)

Skip the crowds this is a private tour for your group only! “Lincoln Park Spirits: A Ghostly Walk Through Chicago’s Past” takes you on an eerie exploration of the Lincoln Park neighborhood. Begin at Julia Porter Park, a sere... More

Free Cancellation
Private Tour
Start From $656.64
 
Lincoln Park Spirits Ghost Private Walking Tour Likely to Sell Out

Lincoln Park Spirits Ghost Private Walking Tour

  • Chicago
  • Superb2 reviews5

Skip the crowds this is a private tour for your group only! “Lincoln Park Spirits: A Ghostly Walk ....

    Free Cancellation
    Private Tour
    Start From $656.64
 
 

Echoes of Elegance Private Tour Chicago’s Architectural Splendors

(5 of 2 reviews)

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultur... More

Free Cancellation
Private Tour
Start From $656.64
 
Echoes of Elegance Private Tour Chicago’s Architectural Splendors Likely to Sell Out

Echoes of Elegance Private Tour Chicago’s Architectural Splendo....

  • Chicago
  • Superb2 reviews5

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through ....

    Free Cancellation
    Private Tour
    Start From $656.64
 
 

4 Hours of Chicago City Tour Sedan

(5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $640.00
 
4 Hours of Chicago City Tour Sedan Likely to Sell Out

4 Hours of Chicago City Tour Sedan

  • Chicago
  • Superb2 reviews5

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating....

    Free Cancellation
    Private Tour
    Start From $640.00
 
 

Private Walking Tour of Chicago’s Artsy Cultural Landmarks

(5 of 2 reviews)

Skip the crowds this is a private tour for your group only! 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... More

Free Cancellation
Private Tour
Start From $656.64
 
Private Walking Tour of Chicago’s Artsy Cultural Landmarks Likely to Sell Out

Private Walking Tour of Chicago’s Artsy Cultural Landmarks

  • Chicago
  • Superb2 reviews5

Skip the crowds this is a private tour for your group only! Dive into "Chicago's Artsy Cultural Land....

    Free Cancellation
    Private Tour
    Start From $656.64
 
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