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Chicago holidays

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Why go to Chicago

Holidays in Chicago offer an authentic taste of American pie. Sitting on the banks of vast Lake Michigan in the state of Illinois, cosmopolitan Chicago is one of the largest and most popular cities in the US.

If you are looking for holidays to Chicago, use the price-comparison service on TravelSupermarket to find your ideal break...

The so-called Windy City is a sultry mix of history, intrigue and tales of Prohibition-era gangsters, combined with a modern and eclectic city buzz where excellent nightlife and a lively outdoors scene can be enjoyed.

Chicago holidays begin the moment you step off the plane at Chicago O'Hare International Airport (ORD). This busy airport gives you a flavour for the highs you're going to experience in the city.

Home of the deep-dish pizza, an array of beaches, soaring skyscrapers, swathes of parkland and baseball at Wrigley Field, Chicago is a tasty city break destination. Holidays here are also easily combined with road trips to explore more of America's midwest. You could even get your kicks on Route 66 as the famous road begins here and winds its way through the United States of America until it reaches Los Angeles.

Many of Chicago's hotels, restaurants and shops can be found along a stretch of Michigan Avenue known as the Magnificent Mile, and you might opt to pick one of the excellent accommodation options here. You'd certainly be at the heart of the action.

Alternatively, you could select a room overlooking one of Chicago's many green spaces, such as Grant Park, which features museums and galleries and was where President Obama delivered his victory speech in 2008. Grant Park is also home to Millennium Park, which is like a huge rooftop garden sitting atop a parking garage and a railway station.

Tackle the heights of one of Chicago's skyscrapers, such as the Willis Tower, formerly known as the Sears Tower, or the John Hancock Center, where a 95th-floor restaurant offers splendid views to diners. From these heights you can see the city stretch away below you and check out what's left to discover, such as: the attractions of the Loop – the city's historic commercial centre; the Chicago River Esplanade, the sculpture-dotted walk on the north bank of the Chicago River; and Soldier Field, home to NFL's Chicago Bears.

Add all of this to lots of museums and galleries, a thriving dining scene, theatres, clubs and bars, and you'll soon realise that you're never going to get bored in Chicago. And you haven't even tackled sailing or water sports on the grand Lake Michigan yet. Phew!

Start planning your break in Chicago today. You can find and compare prices of holidays by using TravelSupermarket's search tool. Book yours today.

Travel Information




US Dollar ($)

Average flight time(from London)

9 hrs

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*ATOL (Air Travel Organiser's Licence) is a financial protection scheme for package holidays: It provides support to consumers in the event their holiday provider collapses. Booking with an ATOL holder ensures that you won't be left out of pocket and you won't be left stranded abroad. All package holidays compared using TravelSupermarket are protected by ATOL.

ABTA (Association of British Travel Agents) offers similar cover for packages booked with its members. However, while ATOL predominantly covers flight-based packages, ABTA covers non-flight based holidays (such as rail and cruise) and linked travel arrangements. If you are unsure whether or not your trip is covered by ABTA, check with your provider.

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