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

When to find the cheapest flights to Chicago

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • day of search
  • price
  • departure city
outbound: Jun 30, 2018
1 stop (4h34m)
American Airlines
return: Jul 6, 2018
direct (3h11m)
American Airlines
outbound: Jun 23, 2018
direct (2h57m)
Frontier Airlines
return: Jun 30, 2018
direct (3h08m)
Spirit Airlines
outbound: Jun 23, 2018
direct (2h41m)
United Airlines
return: Jun 30, 2018
direct (2h51m)
United Airlines
outbound: Jun 23, 2018
1 stop (26h01m)
JetBlue
return: Jun 30, 2018
2 stops (18h43m)
JetBlue
outbound: Jun 3, 2018
1 stop (5h13m)
Delta Air Lines
return: Jun 10, 2018
1 stop (8h54m)
United Airlines
outbound: Jun 6, 2018
direct (2h29m)
Spirit Airlines
return: Jun 9, 2018
direct (2h39m)
Spirit Airlines
outbound: Jun 6, 2018
direct (2h21m)
United Airlines
return: Jun 9, 2018
direct (2h39m)
Spirit Airlines
outbound: May 24, 2018
direct (2h37m)
JetBlue
return: May 29, 2018
direct (2h09m)
JetBlue
outbound: May 24, 2018
direct (2h21m)
United Airlines
return: May 29, 2018
direct (2h10m)
United Airlines
outbound: May 30, 2018
1 stop (5h56m)
Spirit Airlines
return: Jun 9, 2018
direct (2h59m)
Spirit Airlines
outbound: Jun 2, 2018
direct (2h17m)
American Airlines
return: Jun 6, 2018
direct (2h28m)
American Airlines
outbound: Jun 1, 2018
direct (2h26m)
Spirit Airlines
return: Jun 3, 2018
direct (2h02m)
Frontier Airlines
outbound: Oct 9, 2018
direct (2h40m)
Southwest Airlines
return: Oct 16, 2018
direct (2h15m)
Southwest Airlines
outbound: Sep 7, 2018
1 stop (6h45m)
Southwest Airlines
return: Sep 9, 2018
direct (2h)
Southwest Airlines
outbound: Jul 10, 2018
1 stop (7h10m)
Delta Air Lines
return: Jul 19, 2018
1 stop (4h38m)
Delta Air Lines
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Return
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Choose your departure month

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
    • May 2018
    • June 2018
    • July 2018
    • August 2018
    • September 2018
    • October 2018
    • November 2018
    • December 2018
    • January 2019
    • February 2019
    • March 2019
    • April 2019
    • popularity
    • price
    • departure city
    outbound: May 26, 2018
    direct (4h12m)
    Spirit Airlines
    return: May 28, 2018
    direct (4h23m)
    Spirit Airlines
    outbound: Aug 15, 2018
    direct (3h46m)
    Frontier Airlines
    return: Aug 22, 2018
    direct (3h50m)
    Frontier Airlines
    outbound: May 27, 2018
    direct (3h35m)
    Spirit Airlines
    return: Jun 3, 2018
    direct (4h11m)
    Frontier Airlines
    outbound: Jun 2, 2018
    direct (2h26m)
    Spirit Airlines
    return: Jun 6, 2018
    direct (2h30m)
    Spirit Airlines
    outbound: Jul 11, 2018
    direct (3h01m)
    Frontier Airlines
    return: Jul 18, 2018
    direct (2h59m)
    Frontier Airlines
    outbound: Jun 6, 2018
    direct (2h29m)
    Spirit Airlines
    return: Jun 9, 2018
    direct (2h39m)
    Spirit Airlines
    outbound: Jun 2, 2018
    direct (2h11m)
    Spirit Airlines
    return: Jun 6, 2018
    direct (2h01m)
    Spirit Airlines
    outbound: Jun 2, 2018
    direct (2h36m)
    Spirit Airlines
    return: Jun 5, 2018
    direct (2h23m)
    Spirit Airlines
    outbound: Jun 7, 2018
    direct (8h26m)
    Frontier Airlines
    return: Jun 11, 2018
    direct (7h13m)
    Frontier Airlines
    outbound: Jun 3, 2018
    direct (2h37m)
    Spirit Airlines
    return: Jun 10, 2018
    direct (2h48m)
    Spirit Airlines
    outbound: Jun 7, 2018
    direct (3h10m)
    United Airlines
    return: Jul 1, 2018
    direct (3h08m)
    United Airlines
    outbound: Jun 17, 2018
    direct (2h15m)
    Southwest Airlines
    return: Jun 19, 2018
    direct (2h02m)
    Frontier Airlines
    outbound: May 25, 2018
    direct (4h09m)
    Spirit Airlines
    return: May 28, 2018
    direct (4h21m)
    Spirit Airlines
    outbound: Jun 21, 2018
    direct (3h15m)
    Spirit Airlines
    return: Jul 6, 2018
    direct (3h03m)
    Spirit Airlines
    outbound: May 24, 2018
    1 stop (4h25m)
    Delta Air Lines
    return: May 27, 2018
    direct (2h16m)
    United Airlines
    outbound: May 27, 2018
    1 stop (3h37m)
    Delta Air Lines
    return: Jun 3, 2018
    1 stop (7h19m)
    Delta Air Lines
    outbound: Jun 7, 2018
    1 stop (13h08m)
    Frontier Airlines
    return: Jun 11, 2018
    direct (2h50m)
    Spirit Airlines
    outbound: Jul 24, 2018
    direct (2h38m)
    United Airlines
    return: Jul 31, 2018
    direct (2h44m)
    United Airlines
    outbound: Jun 7, 2018
    direct (2h10m)
    Spirit Airlines
    return: Jun 9, 2018
    direct (1h47m)
    Spirit Airlines