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

When to find the cheapest flights to Chicago

  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • day of search
  • price
  • departure city
outbound: Sep 10, 2018
direct (2h23m)
United Airlines
return: Sep 15, 2018
direct (2h28m)
Spirit Airlines
outbound: Jul 29, 2018
direct (2h34m)
JetBlue
return: Aug 5, 2018
direct (2h10m)
Spirit Airlines
outbound: Sep 6, 2018
direct (2h45m)
JetBlue
return: Sep 10, 2018
direct (2h30m)
Spirit Airlines
outbound: Aug 8, 2018
direct (2h25m)
Spirit Airlines
return: Aug 15, 2018
direct (2h10m)
Spirit Airlines
outbound: Aug 25, 2018
direct (2h24m)
Spirit Airlines
return: Aug 28, 2018
direct (2h23m)
Spirit Airlines
outbound: Aug 28, 2018
direct (2h52m)
United Airlines
return: Sep 5, 2018
direct (2h47m)
United Airlines
outbound: Sep 14, 2018
direct (2h36m)
American Airlines
return: Sep 18, 2018
direct (3h04m)
American Airlines
outbound: Aug 3, 2018
1 stop (4h40m)
American Airlines
return: Aug 7, 2018
direct (2h10m)
American Airlines
outbound: Aug 21, 2018
direct (2h26m)
American Airlines
return: Aug 29, 2018
direct (2h18m)
American Airlines
outbound: Aug 14, 2018
direct (2h59m)
Frontier Airlines
return: Aug 21, 2018
direct (3h01m)
Frontier Airlines
outbound: Sep 27, 2018
direct (3h10m)
Frontier Airlines
return: Oct 2, 2018
direct (2h53m)
Frontier Airlines
outbound: Sep 1, 2018
1 stop (4h54m)
Delta Air Lines
return: Sep 6, 2018
1 stop (4h55m)
Delta Air Lines
outbound: Aug 29, 2018
direct (2h42m)
Spirit Airlines
return: Sep 5, 2018
direct (3h05m)
Spirit Airlines
outbound: Aug 1, 2018
direct (2h24m)
United Airlines
return: Aug 7, 2018
direct (2h13m)
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

    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!

    Before you go to Chicago

    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
    • July 2018
    • August 2018
    • September 2018
    • October 2018
    • November 2018
    • December 2018
    • January 2019
    • February 2019
    • March 2019
    • April 2019
    • May 2019
    • June 2019
    • popularity
    • price
    • departure city
    outbound: Aug 21, 2018
    direct (3h16m)
    United Airlines
    return: Aug 28, 2018
    direct (3h45m)
    United Airlines
    outbound: Oct 1, 2018
    direct (3h48m)
    United Airlines
    return: Oct 10, 2018
    direct (4h23m)
    United Airlines
    outbound: Aug 17, 2018
    direct (3h41m)
    Frontier Airlines
    return: Aug 21, 2018
    direct (4h06m)
    Frontier Airlines
    outbound: Aug 8, 2018
    direct (2h25m)
    Spirit Airlines
    return: Aug 14, 2018
    direct (2h16m)
    Spirit Airlines
    outbound: Aug 25, 2018
    direct (2h24m)
    Spirit Airlines
    return: Aug 28, 2018
    direct (2h23m)
    Spirit Airlines
    outbound: Oct 3, 2018
    direct (2h27m)
    Spirit Airlines
    return: Oct 16, 2018
    direct (2h41m)
    Spirit Airlines
    outbound: Aug 17, 2018
    direct (2h31m)
    Spirit Airlines
    return: Aug 20, 2018
    direct (2h13m)
    Spirit Airlines
    outbound: Aug 22, 2018
    direct (2h37m)
    Spirit Airlines
    return: Aug 28, 2018
    direct (2h40m)
    Spirit Airlines
    outbound: Sep 27, 2018
    direct (3h10m)
    Frontier Airlines
    return: Oct 2, 2018
    direct (2h53m)
    Frontier Airlines
    outbound: Sep 5, 2018
    1 stop (8h31m)
    Spirit Airlines
    return: Sep 12, 2018
    1 stop (7h03m)
    Spirit Airlines
    outbound: Aug 11, 2018
    1 stop (7h31m)
    Delta Air Lines
    return: Aug 18, 2018
    direct (3h08m)
    United Airlines
    outbound: Jul 27, 2018
    1 stop (12h28m)
    Spirit Airlines
    return: Jul 30, 2018
    1 stop (10h44m)
    Spirit Airlines
    outbound: Aug 30, 2018
    direct (1h49m)
    United Airlines
    return: Sep 2, 2018
    direct (1h49m)
    United Airlines
    outbound: Aug 17, 2018
    direct (4h03m)
    Spirit Airlines
    return: Aug 20, 2018
    direct (4h11m)
    Spirit Airlines
    outbound: Aug 9, 2018
    direct (1h14m)
    United Airlines
    return: Aug 12, 2018
    direct (1h23m)
    United Airlines
    outbound: Aug 16, 2018
    direct (3h11m)
    Spirit Airlines
    return: Aug 19, 2018
    direct (2h58m)
    Spirit Airlines
    outbound: Oct 20, 2018
    direct (1h32m)
    United Airlines
    return: Oct 22, 2018
    direct (1h35m)
    United Airlines
    outbound: Sep 6, 2018
    direct (2h49m)
    Spirit Airlines
    return: Sep 10, 2018
    direct (2h30m)
    Spirit Airlines
    outbound: Sep 14, 2018
    1 stop (28h24m)
    Frontier Airlines
    return: Sep 16, 2018
    1 stop (24h27m)
    Spirit Airlines
    outbound: Oct 1, 2018
    1 stop (39h)
    Eva Air
    return: Dec 12, 2018
    1 stop (32h30m)
    Eva Air