Top activities
Top landmarks
Trip ideas
Nearby places

Top Chicago Luxury Tours

201 Results
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

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

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

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

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

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

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

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

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

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

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
Roundtrip Shuttle to South Side and Obama Presidential Center

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important …More

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important...

30 minutes Free Cancellation
4.5 (20)
from
$10
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent …More

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...

7 days Free Cancellation
5.0 (3)
from
$11
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

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

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
Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once …More

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once...

1 hour 30 minutes Free Cancellation
5.0 (27)
from
$15
Explore Chicago’s Indoor Mushroom Farm Experience

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushrooms were …More

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushrooms were...

1 hour 30 minutes Free Cancellation
4.5 (6)
from
$20
Embers of the Windy City: Chilling Chicago Ghost Tours

Come on our chilling ghost tour presented by US Ghost Adventures! Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks …More

Come on our chilling ghost tour presented by US Ghost Adventures! Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks...

1 hour Free Cancellation
4.6 (137)
from
$26
Frank Lloyd Wright Robie House Admission

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. …More

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture....

1 hour Free Cancellation
4.4 (152)
from
$27
West Town Hot Spots Tour By Studio W.I.P.

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. …More

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art....

90 to 105 minutes Free Cancellation
5.0 (3)
from
$27
Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich …More

Likely to Sell Out
Likely to Sell Out

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich...

45 minutes Free Cancellation
4.8 (3,582)
from
$28

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Chicago Tours
Attractions
Guides
Calendar