When to find the cheapest flights to Chicago

  • any
  • August 2017
  • September 2017
  • October 2017
  • November 2017
  • December 2017
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • day of search
  • price
  • departure city
outbound: Oct 8, 2017
direct (2h40m)
Spirit Airlines
return: Oct 14, 2017
direct (2h09m)
Spirit Airlines
outbound: Sep 10, 2017
direct (2h38m)
JetBlue
return: Sep 23, 2017
direct (2h09m)
Spirit Airlines
outbound: Oct 25, 2017
direct (2h20m)
Southwest Airlines
return: Oct 28, 2017
direct (2h05m)
Southwest Airlines
outbound: Oct 21, 2017
direct (1h20m)
American Airlines
return: Oct 28, 2017
direct (1h25m)
American Airlines
outbound: Oct 21, 2017
direct (1h35m)
Southwest Airlines
return: Oct 28, 2017
direct (1h25m)
Southwest Airlines
outbound: Sep 8, 2017
direct (2h26m)
United Airlines
return: Sep 12, 2017
direct (2h40m)
United Airlines
outbound: Oct 16, 2017
direct (2h27m)
Spirit Airlines
return: Oct 19, 2017
direct (2h26m)
Spirit Airlines
outbound: Nov 19, 2017
direct (2h50m)
United Airlines
return: Nov 28, 2017
direct (2h10m)
United Airlines
outbound: Nov 19, 2017
direct (2h47m)
American Airlines
return: Nov 28, 2017
1 stop (5h14m)
American Airlines
outbound: Dec 5, 2017
direct (2h52m)
Frontier Airlines
return: Dec 11, 2017
direct (2h59m)
Spirit Airlines
outbound: Dec 5, 2017
direct (2h42m)
American Airlines
return: Dec 11, 2017
1 stop (5h23m)
American Airlines
outbound: Sep 19, 2017
direct (2h38m)
Spirit Airlines
return: Sep 26, 2017
direct (3h05m)
Spirit Airlines
outbound: Jan 28, 2018
direct (1h59m)
Delta Air Lines
return: Jan 30, 2018
direct (1h58m)
Spirit Airlines
outbound: Oct 12, 2017
direct (2h40m)
United Airlines
return: Oct 15, 2017
direct (2h59m)
United Airlines
outbound: Oct 24, 2017
1 stop (12h29m)
JetBlue
return: Oct 30, 2017
2 stops (13h56m)
JetBlue
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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

    These Are The Most Family-Friendly Places In The US
    18 August 2017

    Planning an epic family adventure doesn't have to be a headache or break the bank. From Chicago to Yellowstone... these are the most family-friendly destinations in the US so bring the kids along for the ride!

    5 Chicago Instagram Accounts You Need To Follow
    7 July 2017

    From mouth watering cuisine to stunning architecture, explore Chicago like a local with these Instagram accounts showcasing the best of the Windy City.

    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!

    All flight tickets to Chicago (USA)

    • any
    • August 2017
    • September 2017
    • October 2017
    • November 2017
    • December 2017
    • January 2018
    • February 2018
    • March 2018
    • April 2018
    • May 2018
    • June 2018
    • July 2018
    • popularity
    • price
    • departure city
    outbound: Dec 20, 2017
    direct (3h35m)
    Frontier Airlines
    return: Jan 6, 2018
    direct (4h04m)
    Frontier Airlines
    outbound: Oct 25, 2017
    direct (2h20m)
    Southwest Airlines
    return: Oct 28, 2017
    direct (2h05m)
    Southwest Airlines
    outbound: Sep 18, 2017
    direct (4h05m)
    Spirit Airlines
    return: Sep 21, 2017
    direct (4h27m)
    Spirit Airlines
    outbound: Aug 26, 2017
    direct (3h32m)
    Spirit Airlines
    return: Sep 23, 2017
    direct (3h58m)
    Spirit Airlines
    outbound: Oct 31, 2017
    direct (2h41m)
    Spirit Airlines
    return: Nov 11, 2017
    direct (2h50m)
    Spirit Airlines
    outbound: Sep 3, 2017
    direct (2h27m)
    Spirit Airlines
    return: Sep 5, 2017
    direct (2h36m)
    Spirit Airlines
    outbound: Oct 16, 2017
    direct (2h27m)
    Spirit Airlines
    return: Oct 19, 2017
    direct (2h26m)
    Spirit Airlines
    outbound: Jan 28, 2018
    direct (2h12m)
    American Airlines
    return: Jan 30, 2018
    direct (2h06m)
    American Airlines
    outbound: Oct 21, 2017
    direct (2h50m)
    Spirit Airlines
    return: Oct 28, 2017
    direct (2h30m)
    Spirit Airlines
    outbound: Sep 22, 2017
    direct (2h59m)
    United Airlines
    return: Sep 25, 2017
    direct (2h40m)
    United Airlines
    outbound: Sep 18, 2017
    direct (2h10m)
    Southwest Airlines
    return: Sep 20, 2017
    direct (2h05m)
    Southwest Airlines
    outbound: Oct 21, 2017
    direct (1h20m)
    American Airlines
    return: Oct 28, 2017
    direct (1h25m)
    American Airlines
    outbound: Sep 19, 2017
    1 stop (18h)
    Frontier Airlines
    return: Sep 30, 2017
    1 stop (17h39m)
    Frontier Airlines
    outbound: Aug 31, 2017
    1 stop (6h05m)
    Delta Air Lines
    return: Sep 4, 2017
    1 stop (6h01m)
    Delta Air Lines
    outbound: Dec 22, 2017
    direct (1h35m)
    Southwest Airlines
    return: Dec 29, 2017
    direct (1h15m)
    Southwest Airlines
    outbound: Nov 8, 2017
    1 stop (8h54m)
    Spirit Airlines
    return: Nov 12, 2017
    direct (4h35m)
    Delta Air Lines
    outbound: Nov 22, 2017
    direct (2h27m)
    American Airlines
    return: Nov 26, 2017
    direct (1h46m)
    American Airlines
    outbound: Sep 22, 2017
    1 stop (23h10m)
    Frontier Airlines
    return: Sep 26, 2017
    direct (6h14m)
    Frontier Airlines
    outbound: Nov 6, 2017
    1 stop (15h25m)
    Aer Lingus
    return: Nov 13, 2017
    1 stop (10h25m)
    Aer Lingus
    outbound: Sep 1, 2017
    direct (3h48m)
    Spirit Airlines
    return: Sep 4, 2017
    direct (4h31m)
    Spirit Airlines