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

When to find the cheapest flights to Chicago

  • any
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • June 2022
  • July 2022
  • August 2022
  • September 2022
  • October 2022
  • day of search
  • price
  • departure city
Lufthansaoutbound: Jun 10, 2022
1 stop (16h25m)
Lufthansa
Lufthansareturn: Aug 6, 2022
1 stop (25h)
Lufthansa
TAP Air Portugaloutbound: Jun 10, 2022
1 stop (14h05m)
TAP Air Portugal
TAP Air Portugalreturn: Aug 6, 2022
1 stop (31h20m)
TAP Air Portugal
Spirit Airlinesoutbound: Dec 22, 2021
direct (3h19m)
Spirit Airlines
Spirit Airlinesreturn: Dec 27, 2021
direct (4h)
Spirit Airlines
Alaska Airlinesoutbound: Jul 4, 2022
2 stops (14h15m)
Alaska Airlines
Alaska Airlinesreturn: Jul 28, 2022
1 stop (10h28m)
Alaska Airlines
United Airlinesoutbound: Jul 2, 2022
direct (1h21m)
United Airlines
United Airlinesreturn: Jul 27, 2022
direct (1h22m)
United Airlines
Air Canadaoutbound: Jul 30, 2022
1 stop (26h42m)
Air Canada
Austrian Airlinesreturn: Aug 13, 2022
1 stop (13h50m)
Austrian Airlines
United Airlinesoutbound: Jul 30, 2022
1 stop (29h51m)
United Airlines
Austrian Airlinesreturn: Aug 13, 2022
1 stop (13h50m)
Austrian Airlines
Finnairoutbound: Jun 9, 2022
direct (8h05m)
Finnair
Finnairreturn: Aug 6, 2022
direct (9h10m)
Finnair
Frontier Airlinesoutbound: Dec 30, 2021
1 stop (15h29m)
Frontier Airlines
Allegiant Airreturn: Jan 2, 2022
1 stop (21h20m)
Allegiant Air
Allegiant Airoutbound: Dec 23, 2021
1 stop (23h50m)
Allegiant Air
Frontier Airlinesreturn: Dec 27, 2021
1 stop (14h54m)
Frontier Airlines
United Airlinesoutbound: Dec 29, 2021
direct (2h37m)
United Airlines
United Airlinesreturn: Jan 1, 2022
1 stop (12h34m)
United Airlines
Spirit Airlinesoutbound: Dec 30, 2021
1 stop (8h22m)
Spirit Airlines
Spirit Airlinesreturn: Jan 3, 2022
1 stop (6h44m)
Spirit Airlines
Frontier Airlinesoutbound: Dec 3, 2021
1 stop (7h12m)
Frontier Airlines
Frontier Airlinesreturn: Dec 5, 2021
1 stop (16h51m)
Frontier Airlines
JetBlueoutbound: Dec 27, 2021
direct (2h51m)
JetBlue
JetBluereturn: Dec 30, 2021
direct (2h11m)
JetBlue
Delta Air Linesoutbound: Dec 10, 2021
direct (2h39m)
Delta Air Lines
Delta Air Linesreturn: Dec 16, 2021
direct (2h15m)
Delta Air Lines
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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.

    All flight tickets to Chicago (USA)

    • any
    • November 2021
    • December 2021
    • January 2022
    • February 2022
    • March 2022
    • April 2022
    • May 2022
    • June 2022
    • July 2022
    • August 2022
    • September 2022
    • October 2022
    • popularity
    • price
    • departure city
    Icelandairoutbound: Feb 4, 2022
    1 stop (11h10m)
    Icelandair
    Icelandairreturn: Feb 6, 2022
    1 stop (10h30m)
    Icelandair
    United Airlinesoutbound: Dec 1, 2021
    direct (1h32m)
    United Airlines
    United Airlinesreturn: Dec 8, 2021
    direct (1h21m)
    United Airlines
    American Airlinesoutbound: Mar 18, 2022
    direct (1h20m)
    American Airlines
    American Airlinesreturn: Mar 27, 2022
    direct (1h05m)
    American Airlines
    Frontier Airlinesoutbound: Dec 30, 2021
    1 stop (15h29m)
    Frontier Airlines
    Allegiant Airreturn: Jan 2, 2022
    1 stop (21h20m)
    Allegiant Air
    American Airlinesoutbound: Dec 11, 2021
    direct (13h05m)
    American Airlines
    American Airlinesreturn: Dec 25, 2021
    2 stops (21h44m)
    American Airlines
    Spirit Airlinesoutbound: Dec 22, 2021
    direct (3h19m)
    Spirit Airlines
    Spirit Airlinesreturn: Dec 27, 2021
    direct (4h)
    Spirit Airlines