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Top Chicago Luxury Tours

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

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
Bird Tours across Chicago

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested …More

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested...

2 to 5 hours Free Cancellation
5.0 (1)
from
$60
Happy Hour Fireboat Cruise

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this …More

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this...

2 hours Free Cancellation
5.0 (1)
from
$52
Chicago Hauntings Original Ghost Walk through Old Chicago

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's …More

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's...

2 hours
5.0 (1)
from
$40
Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history, …More

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their history,...

1 hour 30 minutes Free Cancellation
5.0 (1)
from
$35
Chinatown Food Tour

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore …More

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore...

3 hours Free Cancellation
5.0 (1)
from
$98
Chicago Photo Capture Your Adventure Walking Tour

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn …More

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$49
Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy …More

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$180
Chicago, Cloud Gate, Grant Park Full-Day City Tour

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the …More

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the...

8 to 10 hours Free Cancellation
4.0 (4)
from
$194
Chicago River Fireworks Cruise

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does …More

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does...

45 minutes
3.3 (3)
from
$32
Chicago Amazing Lakefront Bike Tour

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The …More

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The...

1 hour 30 minutes Free Cancellation
3.6 (8)
from
$49
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
One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, …More

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque,...

9 to 10 hours Hotel pickup offered Free Cancellation
3.0 (2)
from
$315
Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride …More

Likely to Sell Out
Likely to Sell Out

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride...

3 to 7 hours
from
$1,800
Chicago Highlights Running Tour

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” …More

Likely to Sell Out
Likely to Sell Out

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list”...

1 hour 15 minutes Free Cancellation
from
$44
Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in …More

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in...

6 hours Hotel pickup offered Free Cancellation
from
$750
4 Hours of Chicago City Tour Sedan

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

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

4 hours Hotel pickup offered Free Cancellation
from
$640
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
Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show …More

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show...

4 days Free Cancellation
from
$1,030
Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to …More

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

5 hours Hotel pickup offered
from
$443

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

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