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American Holidays to Chicago | Book Flights & Hotel | Cassidy Travel

Chicago

American Holidays to Chicago
Discover the Windy City: Holidays to Chicago - Where Culture and Architecture Dance!
 
Welcome to the dynamic and captivating city of Chicago, where towering skyscrapers, iconic architecture, and a thriving cultural scene create an enticing holiday destination. Located on the shores of Lake Michigan, Chicago, also known as the Windy City, offers a rich blend of history, art, cuisine, and entertainment that will leave you enchanted.
A holiday to Chicago is an extraordinary experience that blends architectural wonders, cultural treasures, and delectable cuisine. Whether you're exploring the iconic landmarks, indulging in the city's vibrant food scene, or soaking in the lakeside charm, Chicago promises an unforgettable journey.
 
Book your dream holiday to the Chicago in the USA today or clikc here and get a quote to discover the fascinating rhythm of this vibrant metropolis with Cassidy Travel.

Browse Selected offers to Chicago

Departure Airport

Destination

Number of Nights

7 to 14

Number of Adults

Number of Children

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Departure Airport

Destination

Number of Nights

7 to 14

Number of Adults

Number of Children

Stops

Filters

Board Basis

Hotel Rating

Price Range

€50 to €3,000

Explore Chicago

Architectural Marvels

The Magnificent Mile
Wander down the Magnificent Mile, Chicago's premier shopping and dining district, lined with majestic skyscrapers and luxury boutiques.
 
Willis Tower Skydeck
Get a bird's-eye view of the city from the Willis Tower Skydeck, standing 1,353 feet above the ground, offering breathtaking vistas of Chicago's skyline.
 
Chicago River Architecture Tour
Embark on a relaxing boat tour along the Chicago River to admire the city's famous architecture, including the Tribune Tower, Wrigley Building, and Marina City.
 

Cultural Treasures

Art Institute of Chicago
Immerse yourself in art at the Art Institute of Chicago, one of the oldest and most renowned art museums in the country, housing an impressive collection from around the world.
 
Millennium Park
Discover the iconic Cloud Gate sculpture, also known as "The Bean," and enjoy outdoor concerts and events at Millennium Park, a green oasis in the heart of the city.
 
Museum Campus
Visit the Museum Campus, home to the Field Museum, the Shedd Aquarium, and the Adler Planetarium, offering a day filled with science, history, and marine life.
 

Culinary Delights

Deep-Dish Pizza
Savor the famous Chicago-style deep-dish pizza, with its thick crust, layers of cheese, and rich tomato sauce, making it a must-try dish while in the city.
 
Chicago Hot Dogs
Bite into the classic Chicago-style hot dog, topped with mustard, onions, relish, tomatoes, pickles, peppers, and celery salt – a true local delicacy.
 
Dining Experience
Foodie Scene: Experience Chicago's vibrant food scene, boasting a diverse array of restaurants serving cuisines from around the world, as well as Michelin-starred fine dining establishments.
 
Nightlife
Jazz and Blues Clubs: Immerse yourself in Chicago's legendary jazz and blues scene at various clubs and bars throughout the city.
 

Festive Season Special

Chicago Christmas Market
Embrace the holiday spirit at the Chicago Christmas Market in Daley Plaza, where twinkling lights, holiday treats, and artisanal gifts await.
 

Lakeside Retreats

Lakefront Trail
Take a leisurely stroll or bike ride along the Lakefront Trail, offering stunning views of Lake Michigan and a refreshing escape from the urban bustle.
 
Chicago Beaches
Enjoy the sun and sand at Chicago's beautiful beaches, such as North Avenue Beach and Oak Street Beach, perfect for relaxation and water activities.