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Flights to Chicago: the Windy City from £355

When you book a cheap flight to Chicago you'll discover this destination, affectionately named 'the windy city', is a truly wonderful place to visit. Chicago is vibrant, exciting and colourful, known for its cultural heritage, fine dining, modern art, sports venues and great shopping sites. There are many wonderful museums in Chicago including the DuSable Museum of African American History, which screens free movies during the summer and presents exhibitions displaying the deeply rich history of African Americans. The Art Institute of Chicago displays high-brow art, including Renoirs, Monet, Tissots and Van Gogh. For those searching for something other than museums, Lake Michigan is a wonderful place to visit. Here you can enjoy beaches, bike rides, scuba diving and magnificent views. You'll be spoiled for choice with the many excellent eateries. The city's cultural mix is reflected in the diversity of restaurants so finding somewhere to spend the evening will never be a problem. Sample Ethiopian cuisine at Ras Dashen or have your fill of succulent seafood at Shaw's Crab House. For sports fanatics, Wrigley Field is the home of the Chicago Cubs and the place to go to catch a ballgame and enjoy some food and beverages. The best thing is that our online price comparison tool can help you to compare hundreds of airlines across the market making your search for a flight from Leeds, Glasgow or anywhere else in the UK even easier. So with one click you can find yourself a cheap flight so that you can enjoy all of the things there are to do in this amazing city.

Prices for flights to Chicago by airline

  • British Airways

    London Chicago

    Tue 01 Nov - Tue 15 Nov

  • KLM

    Southampton Chicago

    Fri 27 Jan - Fri 10 Feb

  • Virgin Atlantic

    Teesside Chicago

    Thu 24 Nov - Tue 29 Nov

Flight destination: Chicago

Your flight will land in O'Hare Airport, which is well-connected transport wise. Trains and buses provide easy access to and from the airport, following your flight. The Metra train is located next to the Parking Lot F and is easily accessed by way of the Airport Transit System. This train takes you all around the city and downtown, including areas like Union Station, LaSalle Street Station and Millennium Station. Chicago Transit Authority (CTA) runs convenient and affordable Blue Line train services from O'Hare Airport. Trains are accessible from Terminal 2 and an airport transit system takes you to the train station. You can also walk there. Vending machines outside the station accept all major credit cards, allowing you to purchase your train ticket. The Pace Bus service also serves O'Hare International Airport, with bus routes 250 and 330 travelling throughout the city's suburbs. You can catch a taxi outside the Baggage Claim terminals, if you prefer to ride in one after your flight. Taxis cost anywhere from 20 to 27 downtown, although prices vary, depending on traffic flow. Woodfield Mall is the largest of its kind in America and closely located near O'Hare airport. If you want to buy some designer clothes, this is the perfect place to do it. There are many fabulous restaurants, like the popular national chain The Cheesecake Cafe Factory, where you can sample quality fusion cuisine and Wicker Park for fresh tasty sushi.

Latest searches for cheap Chicago flights

  • Ryanair LTD

    Liverpool Chicago

    Wed 05 Oct - Wed 12 Oct

  • Ryanair LTD

    Manchester Chicago

    Tue 01 Nov - Tue 15 Nov

  • Ryanair LTD

    Edinburgh Chicago

    Mon 10 Oct - Sun 16 Oct

  • Easyjet

    Glasgow Chicago

    Tue 13 Sep - Tue 20 Sep

  • Ryanair LTD

    Birmingham Chicago

    Sat 04 Feb - Wed 08 Feb

  • Ryanair LTD

    Newcastle Chicago

    Mon 12 Dec - Mon 19 Dec

  • Ryanair LTD

    Leeds Chicago

    Mon 06 Feb - Fri 10 Feb

  • Ryanair LTD

    Bristol Chicago

    Sun 20 Nov - Wed 30 Nov

  • British Airways

    London Chicago

    Tue 01 Nov - Tue 15 Nov

  • Easyjet

    Belfast Chicago

    Thu 06 Oct - Mon 10 Oct

  • British Airways

    Inverness Chicago

    Thu 16 Mar - Thu 23 Mar

  • British Airways

    Aberdeen Chicago

    Wed 08 Feb - Wed 15 Feb

  • Ryanair LTD

    Cardiff Chicago

    Mon 06 Mar - Sun 12 Mar

  • KLM

    Southampton Chicago

    Fri 27 Jan - Fri 10 Feb

  • British Airways

    Jersey Chicago

    Mon 06 Mar - Mon 03 Apr

  • Lufthansa

    Edinburgh Chicago

    Thu 11 May - Wed 17 May

  • Virgin Atlantic

    Teesside Chicago

    Thu 24 Nov - Tue 29 Nov

  • KLM

    Humberside Chicago

    Tue 06 Sep - Wed 28 Sep

  • Virgin Atlantic

    Norwich Chicago

    Mon 24 Oct - Mon 31 Oct

  • Aer Lingus

    Isle of Man Chicago

    Wed 03 Aug - Tue 09 Aug

  • Ryanair LTD

    Bournemouth Chicago

    Tue 02 Aug - Tue 09 Aug