Chicago Holidays 2024 & 2025 • Freedom Destinations
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Chicago Holidays 2024 & 2025 The lake-side city that’s the start of so many USA adventures

Chicago Holidays

Chicago, often called the “Windy City”, is a vibrant and bustling destination in the heart of the United States, attracting millions of visitors each year. Known for its stunning skyline, world-class museums, cultural diversity, and delicious cuisine, Chicago is a must-visit city for anyone planning a holiday in the USA.

During your Chicago holiday, take a stroll along the iconic Lake Michigan, explore the Navy Pier, and visit the famous “Cloud Gate” sculpture in Millennium Park. Don’t forget to catch a “ball game” or to try some of the city’s famous deep-dish pizza and signature hot dogs!

With so much to see and do, Chicago offers something for everyone. So book your Chicago holiday today to experience all this amazing city has to offer.

Plan your holiday

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    Popular Chicago Holiday Ideas

    Some favourite Chicago holiday ideas that can be personalised to suite your plans.

    Chicago Road Trip Holidays

    By car, motorhome or motorcycle, explore the Great Lakes or head out on Route 66.

    Chicago Rail Holidays

    Chicago is well connected for your next holiday by train.

    Discover the East of America

    Cape Cod to Capital City, there’s so much to see in East USA.

    Free Planning Service

    Tell us where you want to go and what you would like to do and we will create your perfect holiday – at a price you can afford.

    call us on 0333 234 0922 or

    Visit Chicago

    Beyond Chicago’s iconic architecture and exciting city centre, is a cultural melting pot of ethnic neighbourhoods just waiting to be explored, they each have their own unique attractions, excellent restaurants and bustling nightlife.

    With jazz and blues music deeply rooted in the culture of Chicago, in the evenings the city comes alive with the sounds of great music pumping from its bustling bars.

    Things To Do In Chicago

    • Visit the Art Institute of Chicago
    • Relax in Chicago’s popular Millennium Park
    • Catch a ball game at Wrigley Field, home to the Chicago Cubs
    • Explore the Museum of Science & Industry
    • Experience the carnival atmosphere on Navy Pier
    • Enjoy breath taking views from the top of the Willis Tower
    • Gaze out over Lake Michigan from the 360° Chicago
    • Shop till you drop on the Magnificent Mile
    • Indulge in the nightlife, dining and entertainment of Lincoln Park

    Getting There

    By Road – Milwaukee 95 miles; Indianapolis 180 miles; St Louis 295 miles

    By Rail – Chicago is a major transport hub offering routes to 46 states, the District of Columbia and three Canadian provinces, the national rail operator Amtrak offers more than 300 trains each day to more than 500 destinations.

    By Air – Direct flights from the UK and most major cities

    Getting Around

    Chicago is a large city but easy to navigate by walking, taxi and public transport. Consider exploring Chicago by neighbourhood to cut down on travel time.

    It’s helpful to think of Chicago as a vertical city, with Lake Michigan as a natural border to the east. Chicago’s numerical grid system is an easy reference point for directions.

    Holidays Designed For You

    Discover America your way. Combine a self drive with a city stay or an escorted tour with a cruise.

    For a holiday designed for you, call 0333 234 0922 or Enquire online