Top Chicago Luxury Tours

Q: What are the best options for Chicago Luxury Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Chicago Luxury Tours are: Pilsen Chicago Walking Tour: Street Art & Mexican History Chicago River Spectacular Fireworks Show and Tiki Bar Cruise Chicago's Secret Interiors Architectural Walking Tour Lakefront Segway Tour in Chicago Downtown Chicago Walking Pizza Tour

Q: What are the best kid-friendly options for Chicago Luxury Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Luxury Tours are: Chicago Architecture River Cruise Chicago River 90 Minute Architecture Tour Chicago Architecture Center River Cruise aboard First Lady Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago Lake and River Architecture Tour View all kid-friendly Tours →

Q: Which Chicago Luxury Tours have Instant Confirmation?

Chicago Luxury Tours with Instant Confirmation include: Chicago Architecture River Cruise Chicago Architecture Center River Cruise aboard First Lady Chicago Favorites Ultimate Food and Walking Tour Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings Chicago's Chinatown Food and Walking Tour View all Tours with Instant Confirmation →

Q: I need a ride! Which Chicago Luxury Tours have Hotel Pickup?

No problem. These Chicago Luxury Tours include Hotel Pickup: Chicago Private Custom City Tour with Hotel Pick Up Chicago Fire TV Show Set Tour Best of Chicago: Premium Small Group City Tour Chicago City Private Tours Chicago P.D. TV Show Set Tour View all Tours with Hotel Pickup →

Q: Got any more Chicago trip ideas?

We sure do. Check out our curated lists of hand-picked Chicago Tours. Top 10 Chicago 2026 Senior-friendly tours Chicago The best tours and activities for culture lovers in Chicago Top Day Trips from Chicago Things to do in Chicago this summer View all Chicago Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Chicago?

Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are: Chicago Luxury & Special Occasions Chicago Luxury Tours Chicago Tours & Sightseeing Chicago Cruises, Sailing & Water Tours Chicago Boat Tours View all tour styles in Chicago →

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At …More

5.0 (29)

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At...

2 hours Free Cancellation

5.0 (29)

from
$275

Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn …More

5.0 (28)

Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn...

90 to 105 minutes Free Cancellation

5.0 (28)

from
$35

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

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views …More

5.0 (27)

Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views...

1 hour 30 minutes Free Cancellation

5.0 (27)

from
$75

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

5.0 (27)

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...

1 hour 30 minutes Free Cancellation

5.0 (27)

from
$15

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired …More

5.0 (26)

Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired...

1 hour 45 minutes Free Cancellation

5.0 (26)

from
$35

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a …More

4.9 (26)

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a...

1 hour 15 minutes

4.9 (26)

from
$42

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local …More

5.0 (25)

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local...

2 hours Hotel pickup offered Free Cancellation

5.0 (25)

from
$315

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in …More

4.8 (24)

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in...

1 hour 30 minutes

4.8 (24)

from
$114

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic …More

5.0 (22)

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...

120 to 150 minutes Free Cancellation

5.0 (22)

from
$71

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean", …More

4.9 (20)

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean",...

2 hours Free Cancellation

4.9 (20)

from
$65

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer …More

4.9 (18)

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer...

2 hours Free Cancellation

4.9 (18)

from
$65

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will …More

5.0 (15)

Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...

45 to 60 minutes Free Cancellation

5.0 (15)

from
$69

The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting …More

4.9 (13)

The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting...

1 hour 30 minutes Free Cancellation

4.9 (13)

from
$45

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how …More

5.0 (12)

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...

2 hours Free Cancellation

5.0 (12)

from
$35

Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this …More

5.0 (12)

Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this...

2 hours 20 minutes

5.0 (12)

from
$44

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior …More

5.0 (11)

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior...

3 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$315

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 Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking …More

5.0 (7)

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking...

2 hours Free Cancellation

5.0 (7)

from
$50