Halloween in Illinois (Updated 2026)

We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together,...
$169

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum,...
$125

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

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

- Chicago's Highest Rated Limo And Car Service - 16 Years in the limousine business - Proven track of exceptional customer service - Professional, Safe,...
$175

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

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

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to...
$75

This guided tour is the ideal way to begin exploring the roots of the author's life and work. It is here that Ernest Hemingway was...
$20

The MCA Chicago is one of the nation’s largest multidisciplinary museums devoted to the art of our time with an international reputation for presenting ground-breaking...
$22

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...
$59

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake...
$24

Why stress about finding a taxi at Chicago's busy airports when you can book a private car in advance? Ensure a smooth ride from Chicago...
$90

The Chicago Theatre Tour Experience
A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and...
$32

#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

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...
$35

Chicago Lakefront Electric Bike Tour
This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...
$69

Enjoy a private and authentic cooking class in a local home with host Ruby who comes from a family that is all about communal eating...
$84

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty,...
$45

