NYC - CHI

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Flights Deals

Cheap Flights from New York to Chicago (NYC-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from New York to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New York to Chicago

Japan Airlines Logo
EWR-ORD
2h 38mnonstop
Japan Airlines Logo
ORD-EWR
2h 14mnonstop
Japan Airlines
Find Deal
Delta Logo
JFK-ORD
2h 56mnonstop
Delta Logo
ORD-JFK
2h 22mnonstop
Air New Zealand Logo
EWR-ORD
2h 38mnonstop
Air New Zealand Logo
ORD-EWR
2h 07mnonstop
Air New Zealand
Find Deal
United Airlines Logo
EWR-ORD
2h 38mnonstop
United Airlines Logo
ORD-EWR
2h 13mnonstop
United Airlines
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GOL Logo
JFK-ORD
3h 01mnonstop
GOL Logo
ORD-JFK
2h 12mnonstop
EL AL Logo
JFK-ORD
2h 56mnonstop
EL AL Logo
ORD-JFK
2h 12mnonstop
Southwest Logo
LGA-MDW
2h 30mnonstop
Southwest Logo
MDW-LGA
2h 05mnonstop
Southwest
Find Deal
Scandinavian Airlines Logo
JFK-ORD
2h 46mnonstop
Scandinavian Airlines Logo
ORD-JFK
2h 23mnonstop
Scandinavian Airlines
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Iberia Logo
JFK-ORD
2h 55mnonstop
Iberia Logo
ORD-JFK
2h 30mnonstop
Iberia
Find Deal
Korean Air Logo
JFK-ORD
2h 56mnonstop
Korean Air Logo
ORD-JFK
2h 24mnonstop
Korean Air
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WestJet Logo
JFK-ORD
2h 56mnonstop
WestJet Logo
ORD-JFK
2h 28mnonstop
WestJet
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Singapore Airlines Logo
JFK-ORD
2h 51mnonstop
Singapore Airlines Logo
ORD-JFK
2h 14mnonstop
Singapore Airlines
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Gulf Air Logo
JFK-ORD
2h 40mnonstop
Gulf Air Logo
ORD-JFK
2h 19mnonstop
Gulf Air
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American Airlines Logo
JFK-ORD
2h 40mnonstop
American Airlines Logo
ORD-JFK
2h 12mnonstop
American Airlines
Find Deal
KLM Logo
JFK-ORD
3h 11mnonstop
KLM Logo
ORD-JFK
2h 23mnonstop
Qatar Airways Logo
JFK-ORD
2h 45mnonstop
Qatar Airways Logo
ORD-JFK
2h 14mnonstop
Qatar Airways
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Air Canada Logo
EWR-ORD
2h 38mnonstop
Air Canada Logo
ORD-EWR
2h 06mnonstop
Air Canada
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Air Europa Logo
JFK-ORD
3h 08mnonstop
Air Europa Logo
ORD-JFK
2h 25mnonstop
Air Europa
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Air France Logo
JFK-ORD
3h 08mnonstop
Air France Logo
ORD-JFK
2h 26mnonstop
Air France
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Emirates Logo
EWR-ORD
2h 44mnonstop
Emirates Logo
ORD-EWR
2h 22mnonstop
Emirates
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China Airlines Logo
JFK-ORD
2h 56mnonstop
China Airlines Logo
ORD-JFK
2h 37mnonstop
China Airlines
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Kenya Airways Logo
JFK-ORD
2h 46mnonstop
Kenya Airways Logo
ORD-JFK
2h 23mnonstop
Kenya Airways
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China Eastern Logo
JFK-ORD
2h 56mnonstop
China Eastern Logo
ORD-JFK
2h 25mnonstop
China Eastern
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Alaska Airlines Logo
JFK-ORD
2h 39mnonstop
Alaska Airlines Logo
ORD-JFK
2h 12mnonstop
Alaska Airlines
Find Deal
Royal Air Maroc Logo
JFK-ORD
2h 53mnonstop
Royal Air Maroc Logo
ORD-JFK
2h 19mnonstop
Royal Air Maroc
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Frontier Logo
JFK-ORD
2h 45mnonstop
Frontier Logo
ORD-JFK
2h 23mnonstop
Frontier
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JetBlue Logo
JFK-ORD
2h 49mnonstop
JetBlue Logo
ORD-JFK
2h 14mnonstop
JetBlue
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Etihad Airways Logo
JFK-ORD
2h 43mnonstop
Etihad Airways Logo
ORD-JFK
2h 14mnonstop
Etihad Airways
Find Deal
LATAM Airlines Logo
JFK-ORD
2h 56mnonstop
LATAM Airlines Logo
ORD-JFK
2h 23mnonstop
LATAM Airlines
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Royal Jordanian Logo
LGA-ORD
2h 39mnonstop
Royal Jordanian Logo
ORD-LGA
2h 14mnonstop
Royal Jordanian
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Finnair Logo
JFK-ORD
2h 51mnonstop
Finnair Logo
ORD-JFK
2h 21mnonstop
Finnair
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ITA Airways Logo
JFK-ORD
2h 56mnonstop
ITA Airways Logo
ORD-JFK
2h 23mnonstop
ITA Airways
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Hawaiian Airlines Logo
JFK-ORD
2h 49mnonstop
Hawaiian Airlines Logo
ORD-JFK
2h 24mnonstop
Hawaiian Airlines
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ANA Logo
EWR-ORD
2h 42mnonstop
ANA Logo
ORD-EWR
2h 13mnonstop
TAP AIR PORTUGAL Logo
EWR-ORD
2h 38mnonstop
TAP AIR PORTUGAL Logo
ORD-EWR
2h 15mnonstop
TAP AIR PORTUGAL
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Spirit Airlines Logo
EWR-ORD
2h 23mnonstop
Spirit Airlines Logo
ORD-EWR
2h 12mnonstop
Spirit Airlines
Find Deal
Virgin Atlantic Logo
JFK-ORD
2h 56mnonstop
Virgin Atlantic Logo
ORD-JFK
2h 23mnonstop
Virgin Atlantic
Find Deal
British Airways Logo
JFK-ORD
2h 40mnonstop
British Airways Logo
ORD-JFK
2h 15mnonstop
British Airways
Find Deal
Booking Insights

KAYAK's insights & trends for New York to Chicago flights

Get data-powered insights and trends into flights from New York to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from New York to Chicago.

Our data shows that the cheapest route for a return flight from New York to Chicago cost ₪303 and was between New York LaGuardia Airport (LGA) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW). The average price for a return flight for this route is ₪303.

What is the cheapest month to fly from New York to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New York to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New York to Chicago is September, where tickets cost ₪596 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is ₪933 and ₪933 respectively.

How far in advance should I book a flight from New York to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New York to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New York to Chicago, you should book around 3 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonJanuary
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 3% increase in price.

When to book flights from New York to Chicago

Are your dates flexible? Find out the best times to travel from New York to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights from New York to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from New York to Chicago 
StephenFlew with United AirlinesEWR-ORDJan 2025
Don't bring a carry on roller bag. It won't fit. They will gate check it. It will take forever.
SheenaFlew with SouthwestLGA-MDWJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
yvgeniFlew with United AirlinesEWR-ORDJan 2024
Check the weather before flying , and don’t rely on getting on time to your destination

FAQs for booking flights from New York to Chicago

  • When looking for flights from New York to Chicago which Chicago airport should I choose?

    Chicago Midway is closer to downtown Chicago, and since it is a smaller airport it can be less busy and easier to navigate; however, because of the airport size difference, Chicago O'Hare International tends to have more flights and is served by more carriers.

  • What is the cost of an Uber from Chicago O'Hare International to downtown Chicago?

    Rides start at $38 but can, of course, be higher depending on the time of day and traffic conditions.

  • What is the best way for someone to pick me up at Chicago O'Hare International?

    Chicago O'Hare International utilizes a cell phone lot for those wishing to pick up arriving passengers. The lot has a flight information display to let those waiting know when you have arrived. The airport does not allow stopping in front of the terminal except for immediate pickup of passengers, so the cell phone lot is an excellent option for those waiting for arriving passengers.

  • What is the fastest way to get to New York LaGuardia airport?

    One very convenient and unique way to get to New York LaGuardia is via the New York City Ferry. You can take the ferry from New York to the last stop at Astoria and then get a taxi or Uber to the airport. The ferry offers alcoholic and non-alcoholic drinks as well as a variety of snacks on board, making it a comfortable journey overall.

  • Which airlines offer Wi-Fi service onboard planes from New York to Chicago?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the New York to Chicago flight route.

  • Which aircraft models fly most regularly from New York to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago flight route.

  • Which airline alliances offer flights from New York to Chicago?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between New York and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from New York to Chicago?

    There are nonstop flights from New York to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from New York to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New York to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New York with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from New York to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for ₪765 or less one-way and ₪932 or less round-trip.
  • Passengers find that when hunger strikes before flights from New York to Chicago, a great place to eat is the New York classic Shake Shack located at Terminal 4 at New York John F. Kennedy International. Shake Shack offers burgers, chicken sandwiches, hot dogs, and, of course, amazing shakes.
  • If man's best friend will also be traveling on your flights from New York to Chicago, each terminal at Newark International offers a pet relief station. The areas at Terminal B and C are pre-security while the area at Terminal A is after security.
  • The Centurion Lounge at New York LaGuardia is a great place to spend some time before flights from New York to Chicago. The lounge offers a dining menu created by one of Zagat’s top 30 under 30 chefs and a cocktail selection created by on the nation's top mixologists.
  • If you do not want to bother with the hustle and bustle of downtown Chicago, there are many hotels located near Chicago O'Hare International that will suit any traveler’s taste and budget. The SpringHill Suites Chicago O'Hare has top-rated service, a convenient location near the airport, and a free airport shuttle. If your whole family is making the trip, the Hilton Garden Inn Chicago O'Hare Airport is just for you, as it includes an indoor pool and kids’ menus.
  • If you are looking for a budget-friendly way to get from Chicago O'Hare International to downtown Chicago, look no further than a ride on the EL Train. The trip costs just a few dollars and will take you right into downtown Chicago. It should be noted that this can be a difficult choice if you are traveling with more than just one or two bags.

Prefer to fly non-stop from New York to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop from New York to Chicago.
Find which airlines fly direct from New York to Chicago, which days they fly and book direct flights.

Nonstop departures

New York to Chicago

Monday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Tuesday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Wednesday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Thursday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Friday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Saturday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Sunday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

See more direct flights

Nonstop returns

Chicago to New York

Monday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Tuesday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Wednesday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Thursday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Friday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Saturday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

Sunday

American Airlines, Delta, JetBlue, +3 more

American Airlines, Delta, +4 more

See more direct flights

Everything you need to know for your flight from New York to Chicago

Cabin class types available on flights from New York to Chicago

Cabin classes available on flights from New York to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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