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Top Chicago Private Sightseeing Tours

61 Results
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Chicago Tours

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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 …More

4.0 (1)

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...

3 days Free Cancellation
4.0 (1)
from
$5
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 your …More

4.1 (7)

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 your...

3 to 9 hours
4.1 (7)
from
$6
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 …More

4.5 (2)

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...

110 to 140 minutes Free Cancellation
4.5 (2)
from
$6
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 …More

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...

45 to 60 minutes
from
$7
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 …More

4.0 (6)

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...

2 hours Free Cancellation
4.0 (6)
from
$8
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 …More

3.9 (11)

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...

1 hour 35 minutes Free Cancellation
3.9 (11)
from
$8
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 …More

3.8 (10)

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...

48 to 78 minutes Free Cancellation
3.8 (10)
from
$8
Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must …More

4.6 (7)

Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must...

50 minutes Free Cancellation
4.6 (7)
from
$9
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 …More

4.8 (6)

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...

60 to 75 minutes Free Cancellation
4.8 (6)
from
$10
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 skyscrapers …More

5.0 (4)

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 skyscrapers...

120 to 150 minutes Free Cancellation
5.0 (4)
from
$10
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 restaurants during the summer …More

4.4 (8)

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 restaurants during the summer...

1 to 2 hours Free Cancellation
4.4 (8)
from
$13
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 …More

4.6 (5)

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...

1 to 2 hours Free Cancellation
4.6 (5)
from
$13
History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became …More

5.0 (31)

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became...

2 hours Free Cancellation
5.0 (31)
from
$33
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 shares stories and …More

Likely to Sell Out
Likely to Sell Out
3.0 (2)

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 shares stories and...

2 hours Hotel pickup offered Free Cancellation
3.0 (2)
from
$34
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 local culture. This locally …More

5.0 (8)

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 local culture. This locally...

1 hour 15 minutes Free Cancellation
5.0 (8)
from
$35
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 …More

5.0 (8)

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...

3 hours Free Cancellation
5.0 (8)
from
$45
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 intimate journey …More

5.0 (1)

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 intimate journey...

2 hours Free Cancellation
5.0 (1)
from
$46
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 shares local stories, …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

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 shares local stories,...

3 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$59
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 …More

5.0 (1)

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...

1 hour Free Cancellation
5.0 (1)
from
$59
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 …More

5.0 (27)

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...

2 hours Free Cancellation
5.0 (27)
from
$59

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