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  • Last Updated: 15th June 2016


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Holidays in Chicago

Holidays in Chicago

Chicago holidays are perfect for those looking to venture to the United States and experience a city break like no other.

Nicknamed the Windy City, tourists can experience a captivating mix of history and culture. Dominated by stunning skyscrapers, the Chicago skyline is recognised across the world and contains some of the finest architecture you’ll ever see. From fascinating museums to lush green parks, and trendy restaurants to vibrant nightlife, there's plenty of activities to fill your time in Chicago!

Find low cost deals on Chicago holidays by searching online or call one of our travel experts on 01772 386386 today.

Chicago holidays - Book your flight & hotel together and SAVE!

hotel offer

4 star_rating MileNorth Chicago

- Set in the Streeterville neighbourhood
- Close to Magnificent Mile & Navy Pier
- 52EIGHTY Rooftop Lounge
- Fitness centre
- Free WiFi

3 night holiday Room Only
Includes return flights from London Heathrow with United Airlines
Departure dates: 29 Oct - 12 Dec 16
Book by: 30 Jun 16

3 nt holiday from
per person
hotel offer

4 star_rating Thompson Chicago

- At the heart of Chicago's Gold Coast
- Close to Lake Michigan
- Dine at Italian restaurant Nico Osteria
- Fitness centre
- Complimentary Wifi

3 night holiday Room Only
Includes return flights from London Heathrow with United Airlines
Departure dates: 29 Oct - 12 Dec 16
Book by: 30 Jun 16

3 nt holiday from
per person

100s more hotels available

Flights to Chicago with

London Heathrow London Gatwick
Manchester Birmingham

Destination Chicago


Although usually overlooked for the 24 hour lifestyle of New York or the hedonistic feel of Los Angeles, Chicago is in fact one of the most fascinating cities in America.

With history that encapsulates everything from 1920s gangsters, to the birth of Jazz and President Obama’s victory speech, you begin to see what shaped this fascinating city. Venture to the numerous museums located throughout Chicago to find out more, such as those at Grant Park; one of the city’s many beautiful green spaces.

Along with various art galleries, a thriving theatre and a party atmosphere that could rival New York; you’ll wonder why you hadn’t thought of the Windy City sooner.

Visiting Chicago? Don't forget your car hire!


USA car hire

America is built for travelling by car. From the freedom of the wide open road to miles of highways and interstates. It’s the best way to discover and explore all the USA has to offer.

The above prices are guidelines only and are correct at the time of publishing. Subject to availability. Other travel dates are available, supplements may apply. Please use the search box or call for details. For more information please read our Pricing Terms and Conditions.