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: Chicago Private Neighborhoods Tour to Lincoln and Hyde Park City Cruises Chicago: Premier Lake Michigan Brunch Cruise Private Chicago Foodie Tour Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour Private Chicago Architecture Walking 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 →

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on …More

5.0 (1)

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on...

2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$999

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local …More

5.0 (1)

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$77

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get …More

5.0 (1)

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get...

2 hours Free Cancellation

5.0 (1)

from
$89

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods …More

5.0 (1)

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$340

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

5.0 (1)

Chicago 6-Hour City Tour by Sedan

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

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$960

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects …More

5.0 (1)

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects...

2 hours Free Cancellation

5.0 (1)

from
$349

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding …More

5.0 (1)

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding...

4 hours Free Cancellation

5.0 (1)

from
$179

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility …More

5.0 (1)

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility...

60 to 70 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$90

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are …More

5.0 (1)

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are...

2 hours Free Cancellation

5.0 (1)

from
$469

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

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour …More

5.0 (1)

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour...

90 to 120 minutes Free Cancellation

5.0 (1)

from
$40

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

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

5.0 (1)

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...

2 to 5 hours Free Cancellation

5.0 (1)

from
$60

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

5.0 (1)

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...

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

5.0 (1)

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...

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

5.0 (1)

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,...

1 hour 30 minutes Free Cancellation

5.0 (1)

from
$35

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

5.0 (1)

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...

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

5.0 (1)

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...

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

5.0 (1)

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...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$180

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. …More

4.6 (3,564)

Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities....

90 to 120 minutes Free Cancellation

4.6 (3,564)

from
$49