NYC - CHI

$94 Find Cheap Flights from New York to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Chicago departing on 4/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
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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 return flight deals from New York to Chicago

Tue, 8 Jul - Tue, 15 Jul
United Airlines Logo
19:54 - 21:36EWR-ORD
2h 42mdirect
United Airlines Logo
06:00 - 09:13ORD-EWR
2h 13mdirect
$210United Airlines
Find Deal
Tue, 12 Aug - Fri, 15 Aug
United Airlines Logo
21:59 - 23:41EWR-ORD
2h 42mdirect
United Airlines Logo
06:00 - 09:13ORD-EWR
2h 13mdirect
$215United Airlines
Find Deal
Fri, 12 Sep - Sun, 14 Sep
United Airlines Logo
06:00 - 07:38EWR-ORD
2h 38mdirect
United Airlines Logo
06:00 - 09:15ORD-EWR
2h 15mdirect
$220United Airlines
Find Deal
Wed, 9 Jul - Wed, 16 Jul
Delta Logo
06:00 - 10:16EWR-ORD
5h 16m1 stop
Delta Logo
11:01 - 15:55ORD-EWR
3h 54m1 stop
$256Delta
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Tue, 8 Jul - Tue, 15 Jul
Spirit Airlines Logo
05:00 - 06:37EWR-ORD
2h 37mdirect
Spirit Airlines Logo
10:00 - 22:56ORD-EWR
11h 56m1 stop
$258Spirit Airlines
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Mon, 30 Jun - Fri, 4 Jul
Spirit Airlines Logo
06:53 - 15:33EWR-ORD
9h 40m1 stop
Spirit Airlines Logo
05:05 - 16:48ORD-EWR
10h 43m1 stop
$269Spirit Airlines
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Sat, 12 Jul - Tue, 15 Jul
Delta Logo
06:00 - 10:10EWR-ORD
5h 10m1 stop
Delta Logo
09:00 - 15:55ORD-EWR
5h 55m1 stop
$272Delta
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Wed, 23 Jul - Fri, 25 Jul
American Airlines Logo
13:30 - 17:37EWR-ORD
5h 07m1 stop
American Airlines Logo
20:29 - 23:59ORD-EWR
2h 30mdirect
$464American Airlines
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Wed, 30 Jul - Thu, 7 Aug
Sun Country Air Logo
11:41 - 19:11EWR-ORD
8h 30m1 stop
Sun Country Air Logo
20:10 - 10:42ORD-EWR
13h 32m1 stop
$468Sun Country Air
Find Deal
Wed, 23 Jul - Thu, 24 Jul
American Airlines Logo
13:30 - 17:37EWR-ORD
5h 07m1 stop
American Airlines Logo
20:29 - 23:59ORD-EWR
2h 30mdirect
$470American Airlines
Find Deal
Useful Info

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 $137 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 this route. The average price for a return flight for this route is $137.

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 $272 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $428 and $411 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. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$94
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Newark to Chicago

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 return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns 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 travellers 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-MDWJune 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.

  • What is the cheapest flight from New York to Chicago?

    In the last 3 days, the lowest price for a flight from New York to Chicago was $61 for a one-way ticket and $137 for a return.

  • 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 direct 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 return 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 $161 or less one-way.
  • 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 direct from New York to Chicago?

Find which airlines fly direct from New York to Chicago, which days they fly and book direct flights.

Direct 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

Direct 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
See more direct flights

Top airline flying from New York to Chicago

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from New York to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.3
Spirit AirlinesOverall score based on 8052 reviews
6.6Boarding
5.1Food
7.1Crew
5.9Comfort
5.0Entertainment
Airline reviews

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

2.0 MediocreBrandi, May 2025MCO - ORD
Read more Spirit Airlines reviews

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Seats were comfortable but dont recline at all. Checkin online was easy but didnt provide a gate until last minute. Flight attendants were very unkind, not friendly and didnt go over safety procedures in case of a crash. No free snacks or beverages, not even water.

Spirit airlines was extremely uncomfortable. The seats were hard.. the constant up selling (from lack of food or even water to $15 for wi fi ) was annoying. Not a recommended airlines

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

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 are not guaranteed.

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