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Chicago city breaks

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*As standard all of our holidays are ATOL protected

Why go to Chicago

Admire the world's densest skyline on city breaks to Chicago, America's ‘Second City’ and birthplace of the skyscraper. Alternatively, if soaring architecture fails to impress, tuck into a delicious deep-dish pizza and get a taste for the USA.

TravelSupermarket compares prices on a range of Chicago city breaks. Get a cuppa, put your feet up and let us help you to find your next trip.

Chicago's skyscrapers rise abruptly from vast Lake Michigan with the Willis Tower peeping above the city skyline. The top attractions are clustered in The Loop, the historic centre circled by the Chicago River, while sandy beaches backed by a string of parks line the shore.

One thing is for certain on a city break to Chicago, you'll never be bored!

Located in the state of Illinois, next to the seemingly infinite waters of Lake Michigan, Chicago is one of America's biggest cities. It's got a great restaurant scene, sports-mad residents, more than a handful of excellent museums, family-friendly amenities, ice-skating in winter, water sports in summer and one of the most rocking live-music scenes in the US. This is a city in which people really live life to the full, and it's the perfect destination for a short break.

Flights arrive into Chicago O'Hare International Airport (ORD) - one of the busiest in the world. From here it's easy to get into the city to check in at your hotel. Many of the best tourist hotels are in the Loop, though visitors are also drawn to accommodation along the Magnificent Mile, Old Town, Lincoln Park and along the Gold Coast.

Wherever you stay, you can make use of the excellent network of public transportation, hail taxis or even hire a car in Chicago to see the main sights. Catch a game of baseball at Wrigley Field, go shopping on the Magnificent Mile, visit Grant Park, amble along the Chicago River Esplanade, drink in the views from the Skydeck of the Willis Tower... there's so much to see and do in Chicago.

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Dollars ($)

Average flight time(from London)

8 hrs 45 mins

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*All deal pricing is accurate as of 3 am on the 12 Nov 2019. Prices are subject to change. Deals are subject to the partners' T&Cs.

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*All deal pricing is accurate as of 3 am on the 12 Nov 2019. Prices are subject to change. Deals are subject to the partners' T&Cs.

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*All deal pricing is accurate as of 3 am on the 12 Nov 2019. Prices are subject to change. Deals are subject to the partners' T&Cs.

*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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