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

When to find the cheapest flights to Chicago

  • any
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • day of search
  • price
  • departure city
Spirit Airlinesoutbound: Nov 4, 2020
direct (2h25m)
Spirit Airlines
Spirit Airlinesreturn: Nov 11, 2020
direct (2h44m)
Spirit Airlines
JetBlueoutbound: Nov 26, 2020
1 stop (11h10m)
JetBlue
JetBluereturn: Nov 29, 2020
direct (2h02m)
JetBlue
American Airlinesoutbound: Nov 26, 2020
2 stops (27h25m)
American Airlines
American Airlinesreturn: Nov 29, 2020
1 stop (6h58m)
American Airlines
Frontier Airlinesoutbound: Nov 22, 2020
direct (2h19m)
Frontier Airlines
Frontier Airlinesreturn: Nov 29, 2020
direct (2h47m)
Frontier Airlines
Alaska Airlinesoutbound: Nov 22, 2020
1 stop (28h23m)
Alaska Airlines
JetBluereturn: Nov 29, 2020
1 stop (17h55m)
JetBlue
American Airlinesoutbound: Nov 13, 2020
direct (3h11m)
American Airlines
American Airlinesreturn: Nov 16, 2020
direct (3h06m)
American Airlines
JetBlueoutbound: Nov 5, 2020
1 stop (20h44m)
JetBlue
Alaska Airlinesreturn: Nov 7, 2020
1 stop (26h45m)
Alaska Airlines
United Airlinesoutbound: Jan 15, 2021
direct (3h20m)
United Airlines
American Airlinesreturn: Jan 17, 2021
direct (3h04m)
American Airlines
United Airlinesoutbound: Nov 20, 2020
direct (2h25m)
United Airlines
United Airlinesreturn: Nov 22, 2020
direct (2h07m)
United Airlines
Spirit Airlinesoutbound: Nov 20, 2020
1 stop (14h20m)
Spirit Airlines
Spirit Airlinesreturn: Nov 22, 2020
1 stop (13h12m)
Spirit 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
    • October 2020
    • November 2020
    • December 2020
    • January 2021
    • February 2021
    • March 2021
    • April 2021
    • May 2021
    • June 2021
    • July 2021
    • August 2021
    • September 2021
    • popularity
    • price
    • departure city
    JetBlueoutbound: Nov 26, 2020
    1 stop (11h10m)
    JetBlue
    JetBluereturn: Nov 29, 2020
    direct (2h02m)
    JetBlue
    American Airlinesoutbound: Nov 13, 2020
    direct (3h11m)
    American Airlines
    American Airlinesreturn: Nov 16, 2020
    direct (3h06m)
    American Airlines
    Spirit Airlinesoutbound: Nov 5, 2020
    direct (2h33m)
    Spirit Airlines
    American Airlinesreturn: Nov 7, 2020
    1 stop (5h32m)
    American Airlines
    Spirit Airlinesoutbound: Nov 19, 2020
    direct (3h03m)
    Spirit Airlines
    Allegiant Airreturn: Nov 22, 2020
    direct (2h22m)
    Allegiant Air
    United Airlinesoutbound: Aug 20, 2021
    direct (50m)
    United Airlines
    Delta Air Linesreturn: Aug 23, 2021
    1 stop (19h21m)
    Delta Air Lines
    American Airlinesoutbound: Nov 4, 2020
    direct (1h24m)
    American Airlines
    Spirit Airlinesreturn: Nov 11, 2020
    1 stop (20h03m)
    Spirit Airlines
    Frontier Airlinesoutbound: Nov 22, 2020
    direct (2h19m)
    Frontier Airlines
    Frontier Airlinesreturn: Nov 29, 2020
    direct (2h47m)
    Frontier Airlines
    Spirit Airlinesoutbound: Nov 6, 2020
    1 stop (6h31m)
    Spirit Airlines
    Spirit Airlinesreturn: Nov 7, 2020
    1 stop (12h03m)
    Spirit Airlines