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

When to find the cheapest flights to Chicago

  • any
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • day of search
  • price
  • departure city
Alaska Airlinesoutbound: Dec 24, 2020
1 stop (7h44m)
Alaska Airlines
Alaska Airlinesreturn: Jan 2, 2021
direct (4h38m)
Alaska Airlines
Spirit Airlinesoutbound: Aug 8, 2020
direct (3h05m)
Spirit Airlines
Spirit Airlinesreturn: Aug 10, 2020
direct (2h52m)
Spirit Airlines
JetBlueoutbound: Sep 9, 2020
direct (2h50m)
JetBlue
JetBluereturn: Sep 23, 2020
direct (2h15m)
JetBlue
American Airlinesoutbound: Sep 9, 2020
direct (2h41m)
American Airlines
American Airlinesreturn: Sep 23, 2020
direct (2h17m)
American Airlines
Frontier Airlinesoutbound: Jul 15, 2021
1 stop (7h47m)
Frontier Airlines
Frontier Airlinesreturn: Jul 18, 2021
1 stop (18h12m)
Frontier Airlines
TAP Air Portugaloutbound: Aug 30, 2020
2 stops (20h55m)
TAP Air Portugal
TAP Air Portugalreturn: Sep 6, 2020
2 stops (24h44m)
TAP Air Portugal
Aer Lingusoutbound: Aug 30, 2020
1 stop (11h40m)
Aer Lingus
Aer Lingusreturn: Sep 6, 2020
1 stop (33h30m)
Aer Lingus
KLMoutbound: Aug 30, 2020
1 stop (11h25m)
KLM
KLMreturn: Sep 6, 2020
1 stop (27h55m)
KLM
United Airlinesoutbound: Aug 30, 2020
1 stop (12h50m)
United Airlines
Swissreturn: Sep 6, 2020
1 stop (13h20m)
Swiss
United Airlinesoutbound: Aug 8, 2020
direct (2h35m)
United Airlines
United Airlinesreturn: Aug 10, 2020
direct (2h42m)
United Airlines
LOT Polish Airlinesoutbound: Aug 21, 2020
2 stops (35h05m)
LOT Polish Airlines
LOT Polish Airlinesreturn: Sep 6, 2020
1 stop (33h15m)
LOT Polish Airlines
Delta Air Linesoutbound: Aug 21, 2020
1 stop (13h51m)
Delta Air Lines
Delta Air Linesreturn: Sep 6, 2020
1 stop (14h17m)
Delta Air Lines
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Departure

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
    • August 2020
    • September 2020
    • October 2020
    • November 2020
    • December 2020
    • January 2021
    • February 2021
    • March 2021
    • April 2021
    • May 2021
    • June 2021
    • July 2021
    • popularity
    • price
    • departure city
    Spirit Airlinesoutbound: Aug 9, 2020
    direct (2h34m)
    Spirit Airlines
    American Airlinesreturn: Aug 16, 2020
    direct (2h25m)
    American Airlines
    Frontier Airlinesoutbound: Aug 28, 2020
    direct (3h26m)
    Frontier Airlines
    Frontier Airlinesreturn: Aug 31, 2020
    direct (3h10m)
    Frontier Airlines
    Frontier Airlinesoutbound: Jul 15, 2021
    1 stop (7h47m)
    Frontier Airlines
    Frontier Airlinesreturn: Jul 18, 2021
    1 stop (18h12m)
    Frontier Airlines
    Frontier Airlinesoutbound: Oct 9, 2020
    1 stop (14h44m)
    Frontier Airlines
    Frontier Airlinesreturn: Oct 12, 2020
    1 stop (20h49m)
    Frontier Airlines
    Spirit Airlinesoutbound: Aug 12, 2020
    1 stop (29h45m)
    Spirit Airlines
    United Airlinesreturn: Aug 19, 2020
    direct (1h30m)
    United Airlines
    Frontier Airlinesoutbound: Aug 9, 2020
    1 stop (27h24m)
    Frontier Airlines
    United Airlinesreturn: Aug 16, 2020
    direct (44m)
    United Airlines