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: River North Food Walking Tour Chicago Walking Tour: Modern Architecture Lincoln Park Hauntings Ghost Investigation Tour Chicago Walking Tour: The Magnificent Mile Lincoln Park Zoo & Nature Museum Private 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: Continental US Train Zephyr Adventure CA -CO - Il Roundtrip Shuttle to South Side and Obama Presidential Center Explore Chicago’s Indoor Mushroom Farm Experience Frank Lloyd Wright Robie House Admission West Town Hot Spots Tour By Studio W.I.P. View all kid-friendly Tours →

Q: Which Chicago Luxury Tours have Instant Confirmation?

Chicago Luxury Tours with Instant Confirmation include: Hyde Park Walking Tour History Race and Urban Change Continental US Train Zephyr Adventure CA -CO - Il Chicago Self-Guided Audio Tour Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio 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 Night Skyline and Lakefront Scenic Tour Best of Chicago: Premium Small Group City Tour Skyline Lakefront and Millennium Park Chicago Private Day Tour Chicago Private Neighborhoods Tour to Lincoln and Hyde Park Frank Lloyd Wright Oak Park Architecture Tour from Chicago 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 →

The Serial Killer and Iconic Chicago Landmarks Bus Tour

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past …More

5.0 (6)

The Serial Killer and Iconic Chicago Landmarks Bus Tour

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past...

1 hour 30 minutes

5.0 (6)

from
$46

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

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of …More

4.7 (184)

Chicago's Original Gangster Tour by Bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of...

1 hour 45 minutes Free Cancellation

4.7 (184)

from
$48

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago …More

5.0 (48)

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago...

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (48)

from
$48

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 (3,567)

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 (3,567)

from
$49

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, …More

4.1 (2,188)

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks,...

2 hours Free Cancellation

4.1 (2,188)

from
$49

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

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

3.6 (8)

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...

1 hour 30 minutes Free Cancellation

3.6 (8)

from
$49

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

Chicago Architecture, History and Culture Loop Walking Tour

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the …More

5.0 (4)

Chicago Architecture, History and Culture Loop Walking Tour

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the...

3 hours Free Cancellation

5.0 (4)

from
$50

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 Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used …More

5.0 (4)

Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$53

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our …More

4.5 (35)

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our...

1 hour 30 minutes

4.5 (35)

from
$54

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the …More

4.8 (519)

Chicago Night Crimes Tour by Bus

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the...

120 to 150 minutes Free Cancellation

4.8 (519)

from
$55

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only …More

5.0 (7,624)

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...

1 hour 30 minutes

5.0 (7,624)

from
$57

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

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
$58

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence …More

4.9 (247)

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...

3 hours Free Cancellation

4.9 (247)

from
$59

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city …More

5.0 (274)

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city...

3 hours Free Cancellation

5.0 (274)

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

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