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

When to find the cheapest flights to Chicago

  • any
  • October 2017
  • November 2017
  • December 2017
  • January 2018
  • February 2018
  • March 2018
  • April 2018
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • day of search
  • price
  • departure city
outbound: Oct 29, 2017
direct (1h32m)
Spirit Airlines
return: Nov 5, 2017
direct (1h30m)
Spirit Airlines
outbound: Dec 27, 2017
direct (3h02m)
JetBlue
return: Jan 2, 2018
direct (2h15m)
JetBlue
outbound: Dec 27, 2017
direct (2h50m)
Southwest Airlines
return: Jan 2, 2018
direct (2h10m)
Southwest Airlines
outbound: Nov 3, 2017
direct (2h24m)
Spirit Airlines
return: Nov 4, 2017
direct (2h15m)
Spirit Airlines
outbound: Dec 27, 2017
direct (2h43m)
Spirit Airlines
return: Jan 3, 2018
direct (2h59m)
Spirit Airlines
outbound: Dec 27, 2017
direct (2h43m)
United Airlines
return: Jan 3, 2018
direct (3h)
United Airlines
outbound: Nov 9, 2017
direct (2h52m)
Frontier Airlines
return: Nov 14, 2017
direct (3h06m)
Frontier Airlines
outbound: Nov 22, 2017
direct (2h41m)
American Airlines
return: Nov 26, 2017
direct (1h59m)
American Airlines
outbound: Nov 22, 2017
1 stop (27h57m)
Virgin America
return: Nov 26, 2017
1 stop (30h39m)
Virgin America
outbound: Nov 1, 2017
direct (3h38m)
United Airlines
return: Nov 3, 2017
1 stop (7h36m)
United Airlines
outbound: Nov 3, 2017
direct (3h)
Frontier Airlines
return: Nov 6, 2017
direct (2h38m)
Spirit Airlines
outbound: Oct 27, 2017
direct (3h19m)
American Airlines
return: Oct 30, 2017
direct (3h02m)
American Airlines
outbound: Feb 8, 2018
1 stop (14h59m)
JetBlue
return: Feb 15, 2018
direct (3h07m)
Frontier Airlines
outbound: Nov 3, 2017
direct (2h35m)
United Airlines
return: Nov 13, 2017
direct (2h17m)
United Airlines
outbound: Nov 2, 2017
1 stop (4h49m)
Delta Air Lines
return: Nov 6, 2017
direct (2h57m)
United Airlines
outbound: Nov 2, 2017
1 stop (7h19m)
American Airlines
return: Nov 6, 2017
direct (2h57m)
United Airlines
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Return
Departure
  • New York
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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.

    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
    • October 2017
    • November 2017
    • December 2017
    • January 2018
    • February 2018
    • March 2018
    • April 2018
    • May 2018
    • June 2018
    • July 2018
    • August 2018
    • September 2018
    • popularity
    • price
    • departure city
    outbound: Nov 21, 2017
    direct (2h33m)
    Spirit Airlines
    return: Nov 26, 2017
    direct (2h47m)
    Spirit Airlines
    outbound: Oct 29, 2017
    direct (1h32m)
    Spirit Airlines
    return: Nov 5, 2017
    direct (1h30m)
    Spirit Airlines
    outbound: Nov 17, 2017
    1 stop (33h05m)
    Qatar Airways
    return: Dec 2, 2017
    1 stop (32h50m)
    Qatar Airways
    outbound: Jun 15, 2018
    1 stop (16h40m)
    Aer Lingus
    return: Jun 18, 2018
    1 stop (10h30m)
    Aer Lingus