Top Chicago City Tours

Q: Which Chicago City Tours have Instant Confirmation?

Chicago City Tours with Instant Confirmation include: Continental US Train Zephyr Adventure CA -CO - Il Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour Roundtrip Shuttle to South Side and Obama Presidential Center Chicago Gangster History Walking Tour of River North View all Tours with Instant Confirmation →

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

No problem. These Chicago City 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 Private Chicago Guided Tour with Hotel Pickup Chicago City Private Tours 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 →

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through …More

5.0 (5)

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through...

2 hours Free Cancellation

5.0 (5)

from
$45

Chicago River 90 Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to …More

4.8 (11,087)

Chicago River 90 Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to...

1 hour 30 minutes Free Cancellation

4.8 (11,087)

from
$45

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years …More

4.8 (2,424)

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years...

1 hour 30 minutes Free Cancellation

4.8 (2,424)

from
$45

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago …More

4.7 (1,607)

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago...

1 hour 30 minutes Free Cancellation

4.7 (1,607)

from
$45

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

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

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 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

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

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

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

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

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. …More

5.0 (394)

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour....

2 hours Free Cancellation

5.0 (394)

from
$67

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold …More

5.0 (131)

Downtown Chicago Walking Pizza Tour

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold...

2 to 3 hours Free Cancellation

5.0 (131)

from
$69

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