Top Chicago Tours & Sightseeing

Q: Which Chicago Tours & Sightseeing have Instant Confirmation?

Chicago Tours & Sightseeing 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 Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour Chicago Scav Hunt - An App-Guided Adventure View all Tours with Instant Confirmation →

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

No problem. These Chicago Tours & Sightseeing 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 →

Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour …More

3.0 (2)

Chicago Scavenger Hunt Adventure

Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour...

3 hours Free Cancellation

3.0 (2)

from
$49

Chicago City Tour with Architecture River Cruise Option

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, & …More

4.8 (727)

Chicago City Tour with Architecture River Cruise Option

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, &...

2 to 4 hours Free Cancellation

4.8 (727)

from
$50

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with curated photo stops at Cloud Gate ("The Bean"), Museum Campus, …More

4.9 (689)

Chicago City Minibus Tour

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with curated photo stops at Cloud Gate ("The Bean"), Museum Campus,...

2 hours Free Cancellation

4.9 (689)

from
$50

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers …More

4.6 (446)

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers...

1 hour 30 minutes Free Cancellation

4.6 (446)

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

Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered …More

4.4 (9)

Professional Photo Shoot in Chicago

Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered...

4 hours Free Cancellation

4.4 (9)

from
$50

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

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, …More

5.0 (4)

Original Chicago Prohibition Bus Tour

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own,...

Free Cancellation

5.0 (4)

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 Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by …More

4.1 (136)

Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...

3 hours Free Cancellation

4.1 (136)

from
$59

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every …More

4.5 (127)

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every...

2 to 3 hours

4.5 (127)

from
$60

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

4.9 (56)

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....

2 hours Free Cancellation

4.9 (56)

from
$60

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

4.5 (17)

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...

1 hour 30 minutes Free Cancellation

4.5 (17)

from
$63

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 (21)

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 (21)

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