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Top things to do in Chicago in Summer (Updated November 2026)

Chicago, USA
Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must …More

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must...

50 minutes Free Cancellation
4.6 (7)
from
$9
Private Photography Session with Local Photographer in Chicago

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. …More

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot....

1 hour Free Cancellation
5.0 (2)
from
$325
Chicago 6-Hour City Tour by Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city …More

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
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 …More

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
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

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
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, …More

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
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

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

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

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

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
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 …More

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

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
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

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

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
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 …More

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

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
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

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
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 …More

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

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

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
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