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

When to find the cheapest flights to Chicago

  • any
  • May 2022
  • June 2022
  • July 2022
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  • December 2022
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  • February 2023
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  • day of search
  • price
  • departure city
Icelandairoutbound: Jun 22, 2022
1 stop (31h15m)
Icelandair
Icelandairreturn: Jul 18, 2022
1 stop (31h45m)
Icelandair
Finnairoutbound: Jun 22, 2022
1 stop (13h45m)
Finnair
British Airwaysreturn: Jul 18, 2022
1 stop (13h10m)
British Airways
Spirit Airlinesoutbound: Jun 4, 2022
1 stop (8h06m)
Spirit Airlines
Spirit Airlinesreturn: Jun 7, 2022
1 stop (9h29m)
Spirit Airlines
American Airlinesoutbound: May 28, 2022
direct (2h41m)
American Airlines
Delta Air Linesreturn: Jun 4, 2022
1 stop (3h53m)
Delta Air Lines
Delta Air Linesoutbound: May 29, 2022
direct (1h27m)
Delta Air Lines
Delta Air Linesreturn: May 30, 2022
direct (1h33m)
Delta Air Lines
Frontier Airlinesoutbound: May 26, 2022
1 stop (29h32m)
Frontier Airlines
Allegiant Airreturn: May 29, 2022
direct (3h43m)
Allegiant Air
Air Canadaoutbound: Jul 29, 2022
1 stop (11h35m)
Air Canada
Swissreturn: Aug 7, 2022
1 stop (28h20m)
Swiss
Swissoutbound: Jul 29, 2022
1 stop (11h25m)
Swiss
Swissreturn: Aug 7, 2022
1 stop (11h45m)
Swiss
Aer Lingusoutbound: Jul 29, 2022
1 stop (10h40m)
Aer Lingus
Aer Lingusreturn: Aug 7, 2022
1 stop (15h35m)
Aer Lingus
Lufthansaoutbound: Jul 29, 2022
1 stop (16h50m)
Lufthansa
Swissreturn: Aug 7, 2022
1 stop (33h30m)
Swiss
United Airlinesoutbound: Jun 21, 2022
direct (4h12m)
United Airlines
United Airlinesreturn: Jun 26, 2022
direct (4h39m)
United Airlines
Alaska Airlinesoutbound: Jun 28, 2022
1 stop (21h38m)
Alaska Airlines
Spirit Airlinesreturn: Jul 2, 2022
direct (4h35m)
Spirit Airlines
Spirit Airlinesoutbound: Jul 14, 2022
direct (3h43m)
Spirit Airlines
Spirit Airlinesreturn: Jul 31, 2022
direct (4h)
Spirit Airlines
JetBlueoutbound: Jul 13, 2022
direct (2h35m)
JetBlue
Allegiant Airreturn: Jul 17, 2022
1 stop (13h45m)
Allegiant Air
Alaska Airlinesoutbound: Sep 1, 2022
1 stop (11h55m)
Alaska Airlines
Alaska Airlinesreturn: Sep 5, 2022
1 stop (22h)
Alaska 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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    Top 10 Things To Do In Chicago This Winter

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    All flight tickets to Chicago (USA)

    • any
    • May 2022
    • June 2022
    • July 2022
    • August 2022
    • September 2022
    • October 2022
    • November 2022
    • December 2022
    • January 2023
    • February 2023
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    • April 2023
    • popularity
    • price
    • departure city
    Frontier Airlinesoutbound: Jun 28, 2022
    1 stop (29h15m)
    Frontier Airlines
    Frontier Airlinesreturn: Jul 2, 2022
    1 stop (14h30m)
    Frontier Airlines
    American Airlinesoutbound: May 28, 2022
    direct (2h41m)
    American Airlines
    Delta Air Linesreturn: Jun 4, 2022
    1 stop (3h53m)
    Delta Air Lines
    United Airlinesoutbound: Nov 18, 2022
    direct (3h06m)
    United Airlines
    United Airlinesreturn: Nov 20, 2022
    direct (2h22m)
    United Airlines
    United Airlinesoutbound: May 27, 2022
    1 stop (12h40m)
    United Airlines
    American Airlinesreturn: May 29, 2022
    direct (1h53m)
    American Airlines
    Spirit Airlinesoutbound: Sep 1, 2022
    1 stop (10h30m)
    Spirit Airlines
    Spirit Airlinesreturn: Sep 7, 2022
    1 stop (10h33m)
    Spirit Airlines
    Spirit Airlinesoutbound: Aug 5, 2022
    direct (2h14m)
    Spirit Airlines
    Spirit Airlinesreturn: Aug 9, 2022
    direct (2h10m)
    Spirit Airlines
    Delta Air Linesoutbound: May 29, 2022
    direct (1h27m)
    Delta Air Lines
    Delta Air Linesreturn: May 30, 2022
    direct (1h33m)
    Delta Air Lines
    Finnairoutbound: Sep 15, 2022
    direct (9h14m)
    Finnair
    Finnairreturn: Sep 22, 2022
    2 stops (18h20m)
    Finnair
    Spirit Airlinesoutbound: Jun 21, 2022
    1 stop (6h38m)
    Spirit Airlines
    Spirit Airlinesreturn: Jun 27, 2022
    1 stop (13h27m)
    Spirit Airlines
    Frontier Airlinesoutbound: May 26, 2022
    1 stop (29h32m)
    Frontier Airlines
    Allegiant Airreturn: May 29, 2022
    direct (3h43m)
    Allegiant Air
    Spirit Airlinesoutbound: Jun 6, 2022
    1 stop (14h13m)
    Spirit Airlines
    American Airlinesreturn: Jun 30, 2022
    1 stop (25h34m)
    American Airlines
    Spirit Airlinesoutbound: Sep 2, 2022
    direct (2h34m)
    Spirit Airlines
    Spirit Airlinesreturn: Sep 5, 2022
    direct (2h21m)
    Spirit Airlines