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: ️ Chicago Instagram Walking Tour (Private & All- Inclusive) Private Chicago Guided Tour with Hotel Pickup Chicago Millennium Park Self-Guided Walking Tour Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour 2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

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: 5-Day Tour of Superior, Huron and Michigan from Chicago Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago Private and All-Inclusive Tour of Chicago Chicago Helicopter Tour: City to Shoreline Chicago Small Group City Tour View all kid-friendly Tours →

Q: Which Chicago Tours & Sightseeing have Instant Confirmation?

Chicago Tours & Sightseeing with Instant Confirmation include: Chicago Exotic Auto Experience Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens Chicago 6-Hour City Tour by Sedan Private 45-Minute Chicago Skyline Helicopter Tour 4-Hour Chicago City Tour by SUV 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 Tour to Lake Geneva and Anderson Japanese Gardens Private Chicago City Minibus Tour Chicago 6-Hour City Tour by Sedan 4-Hour Chicago City Tour by SUV Private City Tour 6-10ppl 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 →

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla, …More

5.0 (2)

2 Hour Bronzeville, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla,...

2 hours Free Cancellation

5.0 (2)

from
$45

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting …More

5.0 (8)

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting...

3 hours Free Cancellation

5.0 (8)

from
$45

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

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! …More

5.0 (256)

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience!...

2 hours Free Cancellation

5.0 (256)

from
$44

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 (432)

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 (432)

from
$43

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a …More

4.9 (26)

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a...

1 hour 15 minutes

4.9 (26)

from
$42

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into …More

4.9 (207)

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into...

2 hours Free Cancellation

4.9 (207)

from
$40

Art Institute of Chicago Admission Ticket

See why the Art Institute of Chicago is the only museum in the world to be top-ranked by Cool Shore Excursions five years in a …More

4.9 (186)

Art Institute of Chicago Admission Ticket

See why the Art Institute of Chicago is the only museum in the world to be top-ranked by Cool Shore Excursions five years in a...

3 hours Free Cancellation

4.9 (186)

from
$40

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier …More

5.0 (25)

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier...

1 to 2 hours Free Cancellation

5.0 (25)

from
$40

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of …More

4.9 (16,682)

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of...

60 to 75 minutes Free Cancellation

4.9 (16,682)

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$39

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional …More

4.9 (1,958)

Chicago River 90-Minute Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional...

1 hour 30 minutes Free Cancellation

4.9 (1,958)

from
$37

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Gain entry into one of the largest interactive torture museums in the USA with this attraction ticket. Explore the museum with an audio guide and …More

4.9 (1,070)

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

Gain entry into one of the largest interactive torture museums in the USA with this attraction ticket. Explore the museum with an audio guide and...

1 hour 30 minutes Free Cancellation

4.9 (1,070)

from
$36

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's …More

5.0 (1,871)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's...

2 hours Free Cancellation

5.0 (1,871)

from
$35

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to …More

4.9 (594)

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to...

2 hours Free Cancellation

4.9 (594)

from
$35

Chicago Walking Tour: Art Deco Skyscrapers Loop

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism …More

4.9 (197)

Chicago Walking Tour: Art Deco Skyscrapers Loop

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism...

1 hour 30 minutes Free Cancellation

4.9 (197)

from
$35

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think …More

5.0 (141)

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think...

2 hours Free Cancellation

5.0 (141)

from
$35

Chicago Architecture Walking Tour: What's New

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on …More

5.0 (90)

Chicago Architecture Walking Tour: What's New

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on...

1 hour 30 minutes Free Cancellation

5.0 (90)

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$35

Chicago Walking Tour: A Walk Through Time

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological …More

4.9 (230)

Chicago Walking Tour: A Walk Through Time

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological...

1 hour 30 minutes Free Cancellation

4.9 (230)

from
$35

Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) …More

4.9 (71)

Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM)...

1 hour 30 minutes Free Cancellation

4.9 (71)

from
$35

Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying …More

5.0 (43)

Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying...

1 hour 45 minutes Free Cancellation

5.0 (43)

from
$35