Top Chicago Tours & Sightseeing

Q: What are the best options for Chicago Tours & Sightseeing?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Chicago Tours & Sightseeing are: 2 Hour Bronzeville, Chicago Tour Roundtrip Shuttle to South Side and Obama Presidential Center Chicago Foods Tour with The Loop, Skyline, Millennium Park Private Chicago Foodie Tour Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Q: What are the best kid-friendly options for Chicago Tours & Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Tours & Sightseeing 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 Tours & Sightseeing have Instant Confirmation?

Chicago Tours & Sightseeing with Instant Confirmation include: Chicago Architecture River Cruise Chicago Architecture Center River Cruise aboard First Lady Chicago Favorites Ultimate Food and Walking Tour Chicago River 90-Minute Architecture Boat Tour Original Chicago Architecture Interiors Tour: Dazzling Interiors 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 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 →

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. …More

5.0 (1)

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT....

2 to 3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$130

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

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

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

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

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

Embark on an engaging scavenger hunt through the historic streets of Chicago! Explore the beautiful Magnificent Mile. Stroll the happening riverwalk See the historic sights …More

5.0 (1)

Magnificent Mile Scavenger Hunt: Chicago Walking Tour and Game

Embark on an engaging scavenger hunt through the historic streets of Chicago! Explore the beautiful Magnificent Mile. Stroll the happening riverwalk See the historic sights...

2 hours Free Cancellation

5.0 (1)

from
$8

Chicago Scav Hunt - An App-Guided Adventure

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a …More

5.0 (1)

Chicago Scav Hunt - An App-Guided Adventure

Take your shot at completing this Chicago Scavenger Hunt around the Loop and River North neighborhoods including the Riverwalk. Complete this solo or build a...

3 hours Free Cancellation

5.0 (1)

from
$8

Hanfu Chinese Traditional Costume Try on

Discover the elegance and beauty of Hanfu, the traditional  clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step …More

5.0 (1)

Hanfu Chinese Traditional Costume Try on

Discover the elegance and beauty of Hanfu, the traditional  clothing of ancient China, in this one-of-a-kind cultural experience here at our Chinatown Visitor Center! Step...

1 day Free Cancellation

5.0 (1)

from
$20

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

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

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 (1,606)

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 (1,606)

from
$45

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views …More

4.6 (897)

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy stunning views...

30 to 45 minutes Free Cancellation

4.6 (897)

from
$30

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 (444)

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 (444)

from
$50

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

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have …More

4.7 (145)

Lakefront Segway Tour in Chicago

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...

1 hour 30 minutes Free Cancellation

4.7 (145)

from
$70