Chicago Luxury Tours

204 Results
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

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
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. …More

Likely to Sell Out
Likely to Sell Out

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

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

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
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
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

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

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
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 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

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

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
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 …More

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

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

Likely to Sell Out
Likely to Sell Out

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

Likely to Sell Out
Likely to Sell Out

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

Likely to Sell Out
Likely to Sell Out

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

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
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 …More

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
Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. …More

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

2 hours Free Cancellation
4.9 (56)
from
$60
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
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, …More

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends,...

2 hours Free Cancellation
4.2 (342)
from
$63
Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to …More

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to...

1 hour 30 minutes Free Cancellation
4.5 (17)
from
$63

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