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

Chicago, USA
173 Results
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

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
Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how …More

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...

2 hours Free Cancellation
5.0 (12)
from
$35
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

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
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

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
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 …More

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)
from
$39
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

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 Key West Private Charters five years in …More

See why the Art Institute of Chicago is the only museum in the world to be top-ranked by Key West Private Charters five years in...

3 hours Free Cancellation
4.9 (186)
from
$40
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

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
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

Likely to Sell Out
Likely to Sell Out

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
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

Likely to Sell Out
Likely to Sell Out

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
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

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

Likely to Sell Out
Likely to Sell Out

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 (11,096)
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

Likely to Sell Out
Likely to Sell Out

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
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 …More

Likely to Sell Out
Likely to Sell Out

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
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, …More

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

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
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

Likely to Sell Out
Likely to Sell Out

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
The Escape Game Chicago: Epic 60-Minute Adventures in River North

Our Chicago location is right off of the famed Michigan Ave next to countless entertainment and dining options, perfect for pairing an escape room with …More

Our Chicago location is right off of the famed Michigan Ave next to countless entertainment and dining options, perfect for pairing an escape room with...

1 hour 15 minutes Free Cancellation
5.0 (433)
from
$48
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 …More

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
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

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
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. …More

Likely to Sell Out
Likely to Sell Out

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 (3,568)
from
$49
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