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

Chicago, USA
173 Results
Chicago Scavenger Hunt Adventure

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to …More

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to...

2 hours Free Cancellation
5.0 (5)
from
$29
Private Chicago Highlights Photography Session

Visitors to Chicago who want to capture fantastic vacation photos shouldn’t settle for smartphone selfies when you can book a professional photographer. With this photo …More

Visitors to Chicago who want to capture fantastic vacation photos shouldn’t settle for smartphone selfies when you can book a professional photographer. With this photo...

1 hour 30 minutes Free Cancellation
5.0 (5)
from
$200
Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the …More

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the...

2 hours Hotel pickup offered Free Cancellation
5.0 (5)
from
$315
Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour …More

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour...

4 hours Hotel pickup offered Free Cancellation
5.0 (4)
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$178
Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, …More

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables,...

2 hours
4.8 (4)
from
$87
Express Chicago Photo Tour of Landmarks

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo …More

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo...

30 to 40 minutes Free Cancellation
5.0 (4)
from
$99
Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers …More

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers...

120 to 150 minutes Free Cancellation
5.0 (4)
from
$10
Original Chicago Prohibition Bus Tour

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, …More

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own,...

Free Cancellation
5.0 (4)
from
$55
Chicago Gangster History Walking Tour of River North

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets. …More

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets....

2 hours Free Cancellation
4.8 (4)
from
$30
Chicago Architecture, History and Culture Loop Walking Tour

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the …More

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the...

3 hours Free Cancellation
5.0 (4)
from
$50
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock …More

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock...

3 hours Free Cancellation
5.0 (3)
from
$109
Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time …More

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time...

2 hours 30 minutes Free Cancellation
5.0 (3)
from
$195
5-Day Tour of Superior, Huron and Michigan from Chicago

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are …More

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are...

5 days Free Cancellation
5.0 (3)
from
$1,180
Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the …More

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the...

4 days Free Cancellation
5.0 (3)
from
$995
Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal …More

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal...

3 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$499
Private City Tour 6-10ppl

PRICE IS PER VEHICLE, AND YOU MAY BRING UP TO 5 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help …More

PRICE IS PER VEHICLE, AND YOU MAY BRING UP TO 5 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help...

3 to 4 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$649
Taste of Chicago's Chinatown Food Tours

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to …More

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to...

3 hours Free Cancellation
5.0 (3)
from
$85
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent …More

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...

7 days Free Cancellation
5.0 (3)
from
$11
Iconic Action Film and Movie Locations 1 Day Tour in Chicago

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On …More

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On...

9 hours Free Cancellation
5.0 (3)
from
$158
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
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