When to find the cheapest flights to Chicago

  • any
  • March 2017
  • April 2017
  • May 2017
  • June 2017
  • July 2017
  • August 2017
  • September 2017
  • October 2017
  • November 2017
  • December 2017
  • January 2018
  • February 2018
  • day of search
  • price
  • departure city
outbound: Jul 23, 2017
direct (3h04m)
Spirit Airlines
return: Jul 30, 2017
direct (2h39m)
Spirit Airlines
outbound: May 26, 2017
direct (3h28m)
United Airlines
return: May 28, 2017
1 stop (7h23m)
United Airlines
outbound: May 26, 2017
1 stop (6h24m)
Virgin America
return: May 28, 2017
1 stop (6h51m)
Virgin America
outbound: May 26, 2017
1 stop (7h47m)
Alaska Airlines
return: May 28, 2017
1 stop (7h59m)
Alaska Airlines
outbound: Apr 5, 2017
direct (2h28m)
Spirit Airlines
return: Apr 19, 2017
direct (2h07m)
Spirit Airlines
outbound: Apr 17, 2017
direct (2h43m)
Unknown Company
return: Apr 20, 2017
direct (3h01m)
Unknown Company
outbound: Mar 29, 2017
direct (2h45m)
United Airlines
return: Apr 5, 2017
direct (2h59m)
Spirit Airlines
outbound: Mar 29, 2017
1 stop (6h19m)
Delta Air Lines
return: Apr 5, 2017
1 stop (6h28m)
Delta Air Lines
outbound: May 10, 2017
direct (2h39m)
United Airlines
return: May 13, 2017
direct (2h13m)
United Airlines
outbound: Aug 27, 2017
direct (2h39m)
Delta Air Lines
return: Aug 30, 2017
direct (2h10m)
American Airlines
outbound: Apr 8, 2017
direct (2h44m)
Frontier Airlines
return: Apr 11, 2017
direct (2h58m)
Spirit Airlines
outbound: Apr 20, 2017
direct (2h36m)
Frontier Airlines
return: Apr 25, 2017
direct (2h46m)
Frontier Airlines
outbound: Apr 18, 2017
direct (2h38m)
Spirit Airlines
return: Apr 25, 2017
direct (2h59m)
Spirit Airlines
outbound: Aug 16, 2017
direct (2h36m)
Unknown Company
return: Aug 18, 2017
1 stop (5h32m)
Unknown Company
outbound: May 3, 2017
direct (2h35m)
American Airlines
return: May 9, 2017
direct (2h10m)
American 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

    Top 10 Things To Do In Chicago This Winter
    9 January 2017

    Looking for a city break this winter with plenty of culture, sights and some winter charm? Chicago may experience sub-zero temperatures at this time of the year, but there's still plenty to do here with snow on the ground!

    Top 5 rooftop bars in Chicago
    27 July 2016

    Soak up the sun and enjoy panoramic views at one of Chicago's finest rooftop bars. Whether it's casual dining, creative cocktails or simply the best views in town - we've got you covered.

    Saved by the Bell diner opens in Chicago
    6 June 2016

    A new pop-up diner in Chicago offers a hit of nostalgia - it's a recreation of Saved by the Bell high school hangout, The Max!

    All flight tickets to Chicago (USA)

    • any
    • March 2017
    • April 2017
    • May 2017
    • June 2017
    • July 2017
    • August 2017
    • September 2017
    • October 2017
    • November 2017
    • December 2017
    • January 2018
    • February 2018
    • popularity
    • price
    • departure city
    outbound: Jul 23, 2017
    direct (3h04m)
    Spirit Airlines
    return: Jul 30, 2017
    direct (2h39m)
    Spirit Airlines
    outbound: May 26, 2017
    direct (3h28m)
    United Airlines
    return: May 28, 2017
    1 stop (7h23m)
    United Airlines
    outbound: Jun 16, 2017
    direct (2h26m)
    Spirit Airlines
    return: Jun 20, 2017
    direct (2h34m)
    Spirit Airlines
    outbound: Apr 1, 2017
    direct (2h09m)
    United Airlines
    return: Apr 8, 2017
    direct (1h53m)
    United Airlines
    outbound: Apr 1, 2017
    1 stop (23h35m)
    Virgin America
    return: Apr 8, 2017
    1 stop (24h)
    Virgin America
    outbound: Jan 15, 2018
    1 stop (13h42m)
    Air France
    return: Jan 22, 2018
    1 stop (11h01m)
    Delta Air Lines
    outbound: May 20, 2017
    1 stop (27h35m)
    Emirates
    return: Jun 10, 2017
    1 stop (36h50m)
    Emirates