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

When to find the cheapest flights to Chicago

  • any
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • day of search
  • price
  • departure city
American Airlinesoutbound: Sep 20, 2019
direct (3h24m)
American Airlines
Frontier Airlinesreturn: Sep 22, 2019
1 stop (18h48m)
Frontier Airlines
Frontier Airlinesoutbound: Sep 20, 2019
1 stop (22h02m)
Frontier Airlines
Frontier Airlinesreturn: Sep 22, 2019
1 stop (18h48m)
Frontier Airlines
Alaska Airlinesoutbound: Sep 20, 2019
1 stop (8h05m)
Alaska Airlines
Alaska Airlinesreturn: Sep 22, 2019
1 stop (19h20m)
Alaska Airlines
Spirit Airlinesoutbound: Aug 24, 2019
direct (2h29m)
Spirit Airlines
Spirit Airlinesreturn: Aug 26, 2019
direct (2h22m)
Spirit Airlines
JetBlueoutbound: Aug 24, 2019
direct (3h08m)
JetBlue
JetBluereturn: Aug 26, 2019
1 stop (8h29m)
JetBlue
Spirit Airlinesoutbound: Aug 26, 2019
direct (2h49m)
Spirit Airlines
Spirit Airlinesreturn: Sep 2, 2019
1 stop (6h15m)
Spirit Airlines
JetBlueoutbound: Aug 26, 2019
1 stop (7h33m)
JetBlue
JetBluereturn: Sep 2, 2019
1 stop (12h34m)
JetBlue
Frontier Airlinesoutbound: Aug 26, 2019
direct (2h44m)
Frontier Airlines
Frontier Airlinesreturn: Sep 2, 2019
1 stop (26h24m)
Frontier Airlines
Spirit Airlinesoutbound: Aug 28, 2019
direct (2h32m)
Spirit Airlines
Spirit Airlinesreturn: Sep 2, 2019
direct (2h25m)
Spirit Airlines
Southwest Airlinesoutbound: Aug 5, 2019
1 stop (15h09m)
Southwest Airlines
Frontier Airlinesreturn: Aug 9, 2019
direct (3h14m)
Frontier Airlines
United Airlinesoutbound: Aug 2, 2019
1 stop (18h28m)
United Airlines
Frontier Airlinesreturn: Aug 9, 2019
1 stop (14h45m)
Frontier Airlines
Delta Air Linesoutbound: Sep 20, 2019
direct (2h35m)
Delta Air Lines
Spirit Airlinesreturn: Sep 23, 2019
direct (2h16m)
Spirit Airlines
American Airlinesoutbound: Jul 24, 2019
direct (2h37m)
American Airlines
American Airlinesreturn: Jul 31, 2019
direct (2h10m)
American Airlines
United Airlinesoutbound: Aug 7, 2019
direct (2h37m)
United Airlines
United Airlinesreturn: Aug 13, 2019
direct (2h24m)
United 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
    • July 2019
    • August 2019
    • September 2019
    • October 2019
    • November 2019
    • December 2019
    • January 2020
    • February 2020
    • March 2020
    • April 2020
    • May 2020
    • June 2020
    • popularity
    • price
    • departure city
    American Airlinesoutbound: Sep 20, 2019
    direct (3h24m)
    American Airlines
    Frontier Airlinesreturn: Sep 22, 2019
    1 stop (18h48m)
    Frontier Airlines
    Spirit Airlinesoutbound: Aug 28, 2019
    direct (2h32m)
    Spirit Airlines
    Spirit Airlinesreturn: Sep 2, 2019
    direct (2h25m)
    Spirit Airlines
    Spirit Airlinesoutbound: Aug 8, 2019
    1 stop (6h50m)
    Spirit Airlines
    Spirit Airlinesreturn: Aug 16, 2019
    direct (4h28m)
    Spirit Airlines
    Spirit Airlinesoutbound: Jul 22, 2019
    direct (3h40m)
    Spirit Airlines
    Frontier Airlinesreturn: Jul 29, 2019
    direct (4h14m)
    Frontier Airlines
    Spirit Airlinesoutbound: Sep 20, 2019
    direct (2h41m)
    Spirit Airlines
    Spirit Airlinesreturn: Sep 23, 2019
    direct (2h45m)
    Spirit Airlines
    Spirit Airlinesoutbound: Aug 24, 2019
    direct (2h29m)
    Spirit Airlines
    Spirit Airlinesreturn: Aug 26, 2019
    direct (2h22m)
    Spirit Airlines
    American Airlinesoutbound: Nov 27, 2019
    direct (2h38m)
    American Airlines
    American Airlinesreturn: Dec 1, 2019
    direct (2h14m)
    American Airlines
    Spirit Airlinesoutbound: Aug 16, 2019
    direct (2h36m)
    Spirit Airlines
    Frontier Airlinesreturn: Aug 20, 2019
    direct (2h48m)
    Frontier Airlines
    Spirit Airlinesoutbound: Oct 1, 2019
    1 stop (8h36m)
    Spirit Airlines
    Spirit Airlinesreturn: Oct 7, 2019
    1 stop (12h53m)
    Spirit Airlines
    American Airlinesoutbound: Sep 25, 2019
    direct (3h22m)
    American Airlines
    American Airlinesreturn: Oct 1, 2019
    direct (3h01m)
    American Airlines
    United Airlinesoutbound: Aug 1, 2019
    direct (2h50m)
    United Airlines
    Southwest Airlinesreturn: Aug 5, 2019
    1 stop (15h09m)
    Southwest Airlines
    Southwest Airlinesoutbound: Aug 2, 2019
    direct (1h35m)
    Southwest Airlines
    United Airlinesreturn: Aug 5, 2019
    direct (1h50m)
    United Airlines
    Spirit Airlinesoutbound: Sep 25, 2019
    direct (3h17m)
    Spirit Airlines
    Spirit Airlinesreturn: Oct 1, 2019
    direct (3h06m)
    Spirit Airlines
    American Airlinesoutbound: Dec 23, 2019
    1 stop (9h55m)
    American Airlines
    United Airlinesreturn: Dec 31, 2019
    direct (2h)
    United Airlines
    Southwest Airlinesoutbound: Aug 1, 2019
    direct (1h15m)
    Southwest Airlines
    Delta Air Linesreturn: Aug 6, 2019
    1 stop (3h36m)
    Delta Air Lines
    Frontier Airlinesoutbound: Aug 15, 2019
    1 stop (10h27m)
    Frontier Airlines
    Spirit Airlinesreturn: Aug 22, 2019
    1 stop (9h15m)
    Spirit Airlines
    Spirit Airlinesoutbound: Oct 22, 2019
    1 stop (7h09m)
    Spirit Airlines
    Alaska Airlinesreturn: Oct 28, 2019
    1 stop (7h45m)
    Alaska Airlines
    Spirit Airlinesoutbound: Sep 13, 2019
    1 stop (7h19m)
    Spirit Airlines
    Spirit Airlinesreturn: Sep 16, 2019
    1 stop (19h01m)
    Spirit Airlines