Cheap flights to Chicago: for art, parks and a giant bean

When to find the cheapest flights to Chicago

  • any
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • day of search
  • price
  • departure city
United Airlinesoutbound: Dec 9, 2019
direct (2h44m)
United Airlines
United Airlinesreturn: Dec 9, 2019
direct (2h17m)
United Airlines
JetBlueoutbound: Dec 9, 2019
1 stop (7h20m)
JetBlue
JetBluereturn: Dec 9, 2019
direct (2h17m)
JetBlue
JetBlueoutbound: Jun 15, 2020
1 stop (9h26m)
JetBlue
JetBluereturn: Jun 21, 2020
1 stop (8h23m)
JetBlue
Alaska Airlinesoutbound: Jun 15, 2020
1 stop (21h)
Alaska Airlines
Alaska Airlinesreturn: Jun 21, 2020
1 stop (12h30m)
Alaska Airlines
Spirit Airlinesoutbound: Feb 13, 2020
direct (3h09m)
Spirit Airlines
Spirit Airlinesreturn: Feb 20, 2020
direct (2h49m)
Spirit Airlines
American Airlinesoutbound: Feb 13, 2020
direct (2h58m)
American Airlines
American Airlinesreturn: Feb 20, 2020
1 stop (5h16m)
American Airlines
American Airlinesoutbound: Mar 18, 2020
direct (2h45m)
American Airlines
United Airlinesreturn: Mar 22, 2020
direct (2h05m)
United Airlines
Delta Air Linesoutbound: Mar 18, 2020
direct (2h49m)
Delta Air Lines
United Airlinesreturn: Mar 22, 2020
direct (2h05m)
United Airlines
JetBlueoutbound: Mar 18, 2020
direct (2h51m)
JetBlue
JetBluereturn: Mar 22, 2020
direct (2h12m)
JetBlue
United Airlinesoutbound: Apr 13, 2020
direct (4h04m)
United Airlines
American Airlinesreturn: Apr 27, 2020
direct (4h21m)
American Airlines
Frontier Airlinesoutbound: Nov 19, 2019
1 stop (11h44m)
Frontier Airlines
United Airlinesreturn: Nov 26, 2019
direct (2h15m)
United Airlines
United Airlinesoutbound: Mar 12, 2020
direct (2h45m)
United Airlines
United Airlinesreturn: Mar 21, 2020
direct (3h01m)
United Airlines
Spirit Airlinesoutbound: Dec 17, 2019
direct (2h42m)
Spirit Airlines
Spirit Airlinesreturn: Dec 28, 2019
direct (2h09m)
Spirit Airlines
Spirit Airlinesoutbound: Jan 22, 2020
direct (2h51m)
Spirit Airlines
Frontier Airlinesreturn: Jan 29, 2020
direct (3h09m)
Frontier Airlines
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Chicago guide: how to get there, what to see

Distance from Chicago city centre
11 km
26 km

Flights to Chicago: need to know

Cheap airline tickets to Chicago

Looking for cheap airfares to Chicago? The Windy City has two main airports, O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW) where you can fly non-stop from New York and across the country onboard American Airlines, Delta, JetBlue, United, among others.[/p]

When to book the cheapest flights to Chicago

If you’re after cheap airfares to Chicago, think about visiting either in spring or fall. Summer is the busiest time of the year. Major holidays like Labor Day and Memorial Day are also popular so make sure you book your flights to Chicago at least 4-5 month before you plan to go.

  • Peak season: Summer, major holidays.
  • Low season: Winter! They don’t call it the Windy City for nothing!
  • Flight duration

    A flight to Chicago from New York takes 2 hours 45 minutes.

    Experience Chicago: sights, tours and activities

    Chicago has a lot going for it. In the summer the city lives for the live music in Millennium Park when festivals like Pitchfork and Lollapalooza roll up. Deep-dish pizza on the waterfront or on the steps of the Art Institute is just the beginning of the foodie treats waiting in Chicago.

    Essentials in Chicago

    Millennium Park: There’s no better place to be in the summertime than Millennium Park. Home to “The Bean,” now a symbol for the city, and other worlds of art, the park also hosts a ton of free concerts at the Pritzker Pavilion. Bring a blanket and a couple of cold ones to enjoy on the lawn while you listen.

    Art Institute of Chicago: As the second largest art museum in the country, you can bet that the Art Institute has a pretty handsome collection. Give yourself at least 2-3 hours to see the museum’s highlights but if you’re really into art, you can easily spend the entire day here.

    Public Art: Chicago has some pretty amazing public art. One piece, known as “The Picasso” was commissioned from the artist when he was 82 years old and was built in steel to his specifications. Across the street is a piece by Joan Miró. Wander around long enough and you’ll stumble upon works by Jean Dubuffet, Marc Chagall and Alexander Calder.

    Visit www.choosechicago.com for more info.

    Hotels and accommodation in Chicago

    Chicago is a convention city with no shortage of hotel rooms. Just keep in mind that during major conventions, hotel room prices shoot up and rooms in certain areas can be scarce. Chicago is a huge city and hotels outside the downtown area are cheaper. Just make sure you have easy access to a CTA train line if you don’t plan to rent a car for your trip.

    Chicago in the Traveler's Edition

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    All flight tickets to Chicago (USA)

    • any
    • November 2019
    • December 2019
    • January 2020
    • February 2020
    • March 2020
    • April 2020
    • May 2020
    • June 2020
    • July 2020
    • August 2020
    • September 2020
    • October 2020
    • popularity
    • price
    • departure city
    Spirit Airlinesoutbound: Feb 13, 2020
    direct (3h24m)
    Spirit Airlines
    Spirit Airlinesreturn: Feb 17, 2020
    direct (4h01m)
    Spirit Airlines
    Spirit Airlinesoutbound: Dec 25, 2019
    direct (2h19m)
    Spirit Airlines
    Spirit Airlinesreturn: Jan 1, 2020
    direct (2h38m)
    Spirit Airlines
    United Airlinesoutbound: Apr 13, 2020
    direct (4h04m)
    United Airlines
    American Airlinesreturn: Apr 27, 2020
    direct (4h21m)
    American Airlines
    United Airlinesoutbound: Dec 9, 2019
    direct (2h44m)
    United Airlines
    United Airlinesreturn: Dec 9, 2019
    direct (2h17m)
    United Airlines
    Spirit Airlinesoutbound: Nov 22, 2019
    1 stop (13h16m)
    Spirit Airlines
    United Airlinesreturn: Nov 24, 2019
    direct (2h03m)
    United Airlines
    Frontier Airlinesoutbound: Nov 24, 2019
    direct (3h33m)
    Frontier Airlines
    Spirit Airlinesreturn: Nov 26, 2019
    direct (3h01m)
    Spirit Airlines
    Spirit Airlinesoutbound: Feb 13, 2020
    direct (3h09m)
    Spirit Airlines
    Spirit Airlinesreturn: Feb 20, 2020
    direct (2h49m)
    Spirit Airlines
    Spirit Airlinesoutbound: Nov 23, 2019
    direct (2h34m)
    Spirit Airlines
    Spirit Airlinesreturn: Nov 30, 2019
    direct (2h51m)
    Spirit Airlines
    Spirit Airlinesoutbound: Dec 21, 2019
    1 stop (6h38m)
    Spirit Airlines
    Spirit Airlinesreturn: Dec 27, 2019
    1 stop (7h59m)
    Spirit Airlines
    Frontier Airlinesoutbound: Nov 19, 2019
    1 stop (13h23m)
    Frontier Airlines
    United Airlinesreturn: Nov 26, 2019
    direct (1h24m)
    United Airlines
    American Airlinesoutbound: Dec 10, 2019
    direct (1h53m)
    American Airlines
    American Airlinesreturn: Dec 10, 2019
    direct (1h50m)
    American Airlines
    American Airlinesoutbound: Nov 19, 2019
    direct (1h37m)
    American Airlines
    United Airlinesreturn: Nov 26, 2019
    direct (1h36m)
    United Airlines
    Spirit Airlinesoutbound: Dec 25, 2019
    1 stop (13h59m)
    Spirit Airlines
    Spirit Airlinesreturn: Dec 30, 2019
    1 stop (15h09m)
    Spirit Airlines
    Frontier Airlinesoutbound: Nov 19, 2019
    1 stop (11h44m)
    Frontier Airlines
    United Airlinesreturn: Nov 26, 2019
    direct (2h15m)
    United Airlines
    JetBlueoutbound: Dec 9, 2019
    1 stop (7h20m)
    JetBlue
    JetBluereturn: Dec 9, 2019
    direct (2h17m)
    JetBlue
    Cape Airoutbound: Jan 24, 2020
    1 stop (4h03m)
    Cape Air
    Cape Airreturn: Jan 24, 2020
    1 stop (16h50m)
    Cape Air
    Spirit Airlinesoutbound: Nov 24, 2019
    direct (3h15m)
    Spirit Airlines
    Spirit Airlinesreturn: Nov 26, 2019
    direct (3h01m)
    Spirit Airlines
    Spirit Airlinesoutbound: Jan 10, 2020
    1 stop (8h10m)
    Spirit Airlines
    Spirit Airlinesreturn: Jan 12, 2020
    1 stop (12h29m)
    Spirit Airlines
    Spirit Airlinesoutbound: Nov 29, 2019
    direct (4h02m)
    Spirit Airlines
    Spirit Airlinesreturn: Dec 1, 2019
    1 stop (26h14m)
    Spirit Airlines
    Air Franceoutbound: Apr 14, 2020
    2 stops (22h35m)
    Air France
    Air Francereturn: Aug 13, 2020
    1 stop (20h)
    Air France