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Things to do on Juneteenth in Chicago (Updated 2026)

Chicago, USA
Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always …More

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always...

2 hours Free Cancellation
5.0 (4)
from
$35
Spanish Paella Cooking Class in Chicago (Includes 3-Course Meal)

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you through …More

Tapas, paella and flan – this hands-on Spanish cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, takes you through...

2 hours 30 minutes Free Cancellation
5.0 (1)
from
$110
Art Boom 3 in 1 : Adults-Only Private Art Experience in Chicago

Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large …More

Likely to Sell Out
Likely to Sell Out

Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large...

1 hour 30 minutes Free Cancellation
4.0 (1)
from
$195
4-Hour Chicago City Tour by SUV

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...

4 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$800
6-Hour Private SUV Transportation Service in Chicago

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 (2)
from
$1,200
Professional Photo Shoot in Chicago

Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered …More

Professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered...

4 hours Free Cancellation
4.4 (9)
from
$50
Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer …More

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer...

1 to 2 hours Free Cancellation
4.4 (8)
from
$13
PRIVATE Online Chicago-Style Deep Dish Pizza Class with Nancy

Enjoy a private and authentic online cooking class and learn to make Nancy's recipe for Chicago-style Deep Dish Pizza, a style of pizza that originated …More

Enjoy a private and authentic online cooking class and learn to make Nancy's recipe for Chicago-style Deep Dish Pizza, a style of pizza that originated...

1 hour 30 minutes Free Cancellation
5.0 (4)
from
$59
Chicago Art Heist: Millennium Park Puzzle Adventure

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided …More

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided...

1 hour 35 minutes Free Cancellation
3.9 (11)
from
$8
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)
from
$179
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

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
Chicago Chinatown: Dragon Kings Puzzle Adventure

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of …More

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of...

48 to 78 minutes Free Cancellation
3.8 (10)
from
$8
2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get …More

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get...

2 hours Free Cancellation
5.0 (1)
from
$89
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
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
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
Luxury SUV O'Hare/Midway Airport (Curbside) Chicago One Way

THE PREMIUM SUV OFFERS SEATING FOR 6 PASSENGERS, WITH LUGGAGE CAPACITY FOR 3 CHECKED-IN BAGS AND 2 CARRY-ON ITEMS. Luxurious Fleet: Our fleet consists of …More

THE PREMIUM SUV OFFERS SEATING FOR 6 PASSENGERS, WITH LUGGAGE CAPACITY FOR 3 CHECKED-IN BAGS AND 2 CARRY-ON ITEMS. Luxurious Fleet: Our fleet consists of...

30 to 60 minutes Hotel pickup offered Free Cancellation
5.0 (3)
from
$205
Private Transfer ORD Airport to Chicago / Milwaukee / Oak Brook

Reliable and convenient transportation to and from the Pickup location. Our professional drivers ensure a smooth journey, providing a stress-free experience for travelers. On-time pickups …More

Reliable and convenient transportation to and from the Pickup location. Our professional drivers ensure a smooth journey, providing a stress-free experience for travelers. On-time pickups...

20 to 45 minutes Hotel pickup offered Free Cancellation
4.0 (2)
from
$21
Curbside Sedan Transfer from O`Hare Airport to Downtown Chicago

Reliable and luxury airport transfers Best and most professional Chauffeurs in the industry Up-to-date luxury vehicles High quality of service Smart rates …More

Reliable and luxury airport transfers Best and most professional Chauffeurs in the industry Up-to-date luxury vehicles High quality of service Smart rates...

30 to 90 minutes Free Cancellation
5.0 (4)
from
$190
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