Things to do on Juneteenth in Chicago (Updated 2026)
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Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became...
$33
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...
$91
Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At...
$275
Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn...
$35
Private Chicago History Museum Tour
Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life...
$59
Chicago Sunset Segway Tour
Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views...
$75
Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once...
$15
Illinois Holocaust Museum presents Experience360 offers a profound journey through the narratives of survival and resilience during the Holocaust and other genocides. This immersive experience...
$12
Intro to Chicago Architecture
Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired...
$35
I am the only person in the US, and possibly the world, that offers this experience. It is both a demonstration and an interactive opportunity...
$85
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...
$42
Experience the best Chicago kayak rentals and Chicago SUP & paddleboard rentals from our unbeatable location at Ohio Street Beach, just steps from Navy Pier...
$40
Chicago Scenic Driving Tour
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local...
$315
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in...
$114
Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...
$71
Skip the stress of a taxi or shared shuttle between Chicago downtown and Midway airport with the Highest rated limousine service in Chicago on Cool Shore...
$142
Chicago’s top-rated limo and car service — with 16+ years of proven service, licensed drivers, and full commercial insurance. Enjoy a safe, private transfer between...
$160
Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean",...
$65
Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer...
$65
#1 Rated Car Service In Chicago Area based on 400 + combined reviews on Cool Shore Excursions, Google and Yelp. We carry newer model luxury...
$133
