NYC - CHI

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1 adult
1 adult, Economy
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Flight 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
LGA-ORD
2h 46mnonstop
Japan Airlines Logo
ORD-LGA
2h 25mnonstop
Japan Airlines
Find Deal
Delta Logo
JFK-ORD
2h 55mnonstop
Delta Logo
ORD-JFK
2h 25mnonstop
Air New Zealand Logo
LGA-ORD
2h 25mnonstop
Air New Zealand Logo
ORD-LGA
2h 07mnonstop
Air New Zealand
Find Deal
United Airlines Logo
LGA-ORD
2h 25mnonstop
United Airlines Logo
ORD-LGA
2h 16mnonstop
United Airlines
Find Deal
GOL Logo
JFK-ORD
3h 07mnonstop
GOL Logo
ORD-JFK
2h 14mnonstop
EL AL Logo
JFK-ORD
2h 55mnonstop
EL AL Logo
ORD-JFK
2h 14mnonstop
Southwest Logo
LGA-MDW
2h 30mnonstop
Southwest Logo
MDW-LGA
2h 00mnonstop
Southwest
Find Deal
Scandinavian Airlines Logo
JFK-ORD
2h 54mnonstop
Scandinavian Airlines Logo
ORD-JFK
2h 25mnonstop
Scandinavian Airlines
Find Deal
Iberia Logo
JFK-ORD
2h 43mnonstop
Iberia Logo
ORD-JFK
2h 19mnonstop
Iberia
Find Deal
Korean Air Logo
JFK-ORD
2h 56mnonstop
Korean Air Logo
ORD-JFK
2h 24mnonstop
Korean Air
Find Deal
WestJet Logo
JFK-ORD
2h 54mnonstop
WestJet Logo
ORD-JFK
2h 23mnonstop
WestJet
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Singapore Airlines Logo
JFK-ORD
2h 53mnonstop
Singapore Airlines Logo
ORD-JFK
2h 17mnonstop
Singapore Airlines
Find Deal
Gulf Air Logo
JFK-ORD
2h 41mnonstop
Gulf Air Logo
ORD-JFK
2h 19mnonstop
Gulf Air
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American Airlines Logo
JFK-ORD
2h 45mnonstop
American Airlines Logo
ORD-JFK
2h 14mnonstop
American Airlines
Find Deal
KLM Logo
JFK-ORD
2h 53mnonstop
KLM Logo
ORD-JFK
2h 26mnonstop
Qatar Airways Logo
JFK-ORD
2h 45mnonstop
Qatar Airways Logo
ORD-JFK
2h 17mnonstop
Qatar Airways
Find Deal
Air Canada Logo
EWR-ORD
2h 38mnonstop
Air Canada Logo
ORD-EWR
2h 15mnonstop
Air Canada
Find Deal
Air Europa Logo
JFK-ORD
3h 01mnonstop
Air Europa Logo
ORD-JFK
2h 20mnonstop
Air Europa
Find Deal
Air France Logo
JFK-ORD
2h 53mnonstop
Air France Logo
ORD-JFK
2h 28mnonstop
Air France
Find Deal
Emirates Logo
LGA-ORD
2h 42mnonstop
Emirates Logo
ORD-LGA
2h 14mnonstop
Emirates
Find Deal
China Airlines Logo
JFK-ORD
2h 56mnonstop
China Airlines Logo
ORD-JFK
2h 36mnonstop
China Airlines
Find Deal
Kenya Airways Logo
JFK-ORD
2h 54mnonstop
Kenya Airways Logo
ORD-JFK
2h 23mnonstop
Kenya Airways
Find Deal
China Eastern Logo
JFK-ORD
2h 53mnonstop
China Eastern Logo
ORD-JFK
2h 25mnonstop
China Eastern
Find Deal
Alaska Airlines Logo
JFK-ORD
2h 45mnonstop
Alaska Airlines Logo
ORD-JFK
2h 14mnonstop
Alaska Airlines
Find Deal
Royal Air Maroc Logo
JFK-ORD
2h 53mnonstop
Royal Air Maroc Logo
ORD-JFK
2h 15mnonstop
Royal Air Maroc
Find Deal
Frontier Logo
JFK-ORD
2h 57mnonstop
Frontier Logo
ORD-JFK
2h 24mnonstop
Frontier
Find Deal
JetBlue Logo
JFK-ORD
2h 50mnonstop
JetBlue Logo
ORD-JFK
2h 17mnonstop
JetBlue
Find Deal
Etihad Airways Logo
JFK-ORD
2h 53mnonstop
Etihad Airways Logo
ORD-JFK
2h 17mnonstop
Etihad Airways
Find Deal
LATAM Airlines Logo
JFK-ORD
2h 56mnonstop
LATAM Airlines Logo
ORD-JFK
2h 25mnonstop
LATAM Airlines
Find Deal
Royal Jordanian Logo
LGA-ORD
2h 50mnonstop
Royal Jordanian Logo
ORD-LGA
2h 10mnonstop
Royal Jordanian
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Finnair Logo
JFK-ORD
2h 51mnonstop
Finnair Logo
ORD-JFK
2h 25mnonstop
Finnair
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Hawaiian Airlines Logo
JFK-ORD
2h 50mnonstop
Hawaiian Airlines Logo
ORD-JFK
2h 17mnonstop
Hawaiian Airlines
Find Deal
ANA Logo
LGA-ORD
2h 48mnonstop
ANA Logo
ORD-LGA
2h 15mnonstop
TAP AIR PORTUGAL Logo
EWR-ORD
2h 42mnonstop
TAP AIR PORTUGAL Logo
ORD-EWR
2h 16mnonstop
TAP AIR PORTUGAL
Find Deal
Spirit Airlines Logo
LGA-ORD
2h 28mnonstop
Spirit Airlines Logo
ORD-LGA
2h 07mnonstop
Spirit Airlines
Find Deal
Virgin Atlantic Logo
JFK-ORD
2h 56mnonstop
Virgin Atlantic Logo
ORD-JFK
2h 22mnonstop
Virgin Atlantic
Find Deal
British Airways Logo
JFK-ORD
2h 43mnonstop
British Airways Logo
ORD-JFK
2h 17mnonstop
British Airways
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by KAYAK users
United's carry-on policy may lead to gate checking.
Expect busy security lines at New York airports.
User tips
User tips
User tips
User tips
Top routes
LGA-ORD
Cheapest • 48% average savings
JFK-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 23% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
Japan Airlines
Mon 15.09
LGA - ORD • Non-stop
Cheapest one-way
Japan Airlines
Mon 15.09
LGA - ORD • Non-stop
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We hope you love your trip to Chicago!
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from New York to Chicago costs ₪300 on the route between New York LaGuardia Airport (LGA) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 48% cheaper than other New York-Chicago routes. The most popular route is between New York John F Kennedy Intl Airport (JFK) and Chicago O'Hare Intl Airport (ORD).

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 January, where tickets cost ₪613 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is ₪929 and ₪922 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 4 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 6% lower on average.

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

  • 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, Star Alliance, and SkyTeam 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 ₪607 or less one-way and ₪961 or less round-trip.

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, Frontier, +4 more

American Airlines, Delta, +5 more

Tuesday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Wednesday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Thursday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Friday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Saturday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Sunday

American Airlines, Delta, JetBlue, +4 more

American Airlines, Delta, +5 more

See more direct flights

Nonstop returns

Chicago to New York

Monday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Tuesday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Wednesday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Thursday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Friday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Saturday

American Airlines, Delta, Frontier, +4 more

American Airlines, Delta, +5 more

Sunday

American Airlines, Delta, JetBlue, +4 more

American Airlines, Delta, +5 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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