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: Private Photography Session with Local Photographer in Chicago Chicago 6-Hour City Tour by Sedan Chicago Self-Guided Audio Tour Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer Luxury SUV 4 Hour Sightseeing 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 →

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start …More

4.6 (5)

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start...

1 to 2 hours Free Cancellation

4.6 (5)

from
$13

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on …More

4.5 (4)

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on...

2 hours Free Cancellation

4.5 (4)

from
$84

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, …More

4.5 (2)

Luxury SUV 4 Hour Sightseeing Tour

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks,...

2 to 4 hours Hotel pickup offered Free Cancellation

4.5 (2)

from
$350

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 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

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, …More

4.0 (27)

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture,...

7 to 10 minutes Free Cancellation

4.0 (27)

from
$150

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ …More

4.3 (20)

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️...

4 to 8 hours Free Cancellation

4.3 (20)

from
$150

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your …More

4.1 (7)

Chicago Self-Guided Audio Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your...

3 to 9 hours

4.1 (7)

from
$6

Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing …More

4.0 (4)

Private Vacation Photoshoot with Photographer in Chicago

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing...

1 hour Free Cancellation

4.0 (4)

from
$137

Chicago, Cloud Gate, Grant Park Full-Day City Tour

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the …More

4.0 (4)

Chicago, Cloud Gate, Grant Park Full-Day City Tour

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the...

8 to 10 hours Free Cancellation

4.0 (4)

from
$194

Lincoln Park Zoo Adventure -An App-Guided Adventure

This self-guided Adventure is perfect for last-minute travelers who love animals and games, and for families traveling with kids! Travelers will use the eATLAS app …More

4.0 (3)

Lincoln Park Zoo Adventure -An App-Guided Adventure

This self-guided Adventure is perfect for last-minute travelers who love animals and games, and for families traveling with kids! Travelers will use the eATLAS app...

45 minutes Free Cancellation

4.0 (3)

from
$8

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely …More

4.0 (2)

Chicago Private Rental Yacht Charter

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely...

3 to 8 hours Free Cancellation

4.0 (2)

from
$1,300

Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the …More

4.0 (1)

Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the...

3 days Free Cancellation

4.0 (1)

from
$5

Museum of Ice Cream Chicago Admission Ticket

Step into a world of color, creativity, and sweetness at the Museum of Ice Cream in Chicago! This immersive, Instagram-worthy experience brings together art, interactive …More

3.6 (431)

Museum of Ice Cream Chicago Admission Ticket

Step into a world of color, creativity, and sweetness at the Museum of Ice Cream in Chicago! This immersive, Instagram-worthy experience brings together art, interactive...

1 hour 30 minutes

3.6 (431)

from
$43

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 Chocolate Tour - An App-Guided Adventure

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and …More

3.0 (7)

Chicago Chocolate Tour - An App-Guided Adventure

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and...

2 hours Free Cancellation

3.0 (7)

from
$8

Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and …More

3.0 (2)

Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and...

2 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$34

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

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, …More

3.0 (2)

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque,...

9 to 10 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$315

Private Photo Session with a Local Photographer in Chicago

Want to capture your amazing honeymoon? Family vacation while the kids are still little? Your perfect couples retreat from everyday busy life? A solo trip …More

3.0 (1)

Private Photo Session with a Local Photographer in Chicago

Want to capture your amazing honeymoon? Family vacation while the kids are still little? Your perfect couples retreat from everyday busy life? A solo trip...

30 minutes

3.0 (1)

from
$285