CHI - NYC

$108 Find Cheap Flights from Chicago to New York

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to New York departing on 28/5. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to New York

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York, 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 Chicago to New York, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to New York (CHI-NYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to New York 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.

Recent return flight deals from Chicago to New York

KAYAK's recommended return flight deals from the most popular airlines that fly from Chicago to New York.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Spirit Airlines Logo
21:08 - 00:29ORD-EWR
2h 21mdirect
Spirit Airlines Logo
05:00 - 06:32EWR-ORD
2h 32mdirect
$160Spirit Airlines
Find Deal
Wed, 4 Jun - Tue, 10 Jun
Spirit Airlines Logo
21:08 - 00:29ORD-EWR
2h 21mdirect
Spirit Airlines Logo
05:55 - 07:27EWR-ORD
2h 32mdirect
$169Spirit Airlines
Find Deal
Sat, 17 May - Tue, 20 May
United Airlines Logo
07:00 - 10:18ORD-LGA
2h 18mdirect
United Airlines Logo
20:30 - 22:09LGA-ORD
2h 39mdirect
$215United Airlines
Find Deal
Sun, 25 May - Tue, 27 May
United Airlines Logo
06:00 - 09:13ORD-EWR
2h 13mdirect
United Airlines Logo
06:00 - 07:38EWR-ORD
2h 38mdirect
$226United Airlines
Find Deal
Sun, 25 May - Tue, 27 May
JetBlue Logo
06:15 - 09:30ORD-JFK
2h 15mdirect
JetBlue Logo
12:00 - 18:36JFK-ORD
7h 36m1 stop
$229JetBlue
Find Deal
Wed, 28 May - Wed, 28 May
JetBlue Logo
06:10 - 09:28ORD-JFK
2h 18mdirect
JetBlue Logo
20:00 - 21:54JFK-ORD
2h 54mdirect
$240JetBlue
Find Deal
Sat, 17 May - Sat, 24 May
Delta Logo
07:00 - 10:12ORD-LGA
2h 12mdirect
Delta Logo
20:55 - 22:41LGA-ORD
2h 46mdirect
$240Delta
Find Deal
Tue, 20 May - Tue, 27 May
Delta Logo
07:00 - 10:25ORD-JFK
2h 25mdirect
Delta Logo
08:00 - 09:51JFK-ORD
2h 51mdirect
$246Delta
Find Deal
Tue, 13 May - Sun, 25 May
Frontier Logo
17:03 - 10:29ORD-JFK
16h 26m1 stop
Frontier Logo
06:59 - 00:06JFK-ORD
18h 07m1 stop
$283Frontier
Find Deal
Wed, 4 Jun - Sat, 7 Jun
Frontier Logo
09:19 - 10:00ORD-JFK
23h 41m1 stop
Frontier Logo
06:00 - 16:41JFK-ORD
11h 41m1 stop
$285Frontier
Find Deal
Sat, 17 May - Tue, 20 May

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

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

What is the cheapest Chicago to New York flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to New York.
Our data shows that the cheapest route for a return flight from Chicago to New York cost $148 and was between Chicago O'Hare Intl Airport (ORD) and New York LaGuardia Airport (LGA). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $148.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to New York, 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 Chicago to New York is September, where tickets cost $243 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $392 and $352 respectively.

Can I save money by flying with a stopover from Chicago to New York?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $469, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to New York, 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 Chicago to New York, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

February

High season

May
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 3% lower on average.

When to book flights from Chicago to New York

Are your dates flexible? Find out the best times to travel from Chicago to New York 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 Chicago to New York: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew the route from Chicago to New York 
Verified travelerFlew with British AirwaysORD-EWRApr 2025
American Eagle definitely does not provide the same quality of service as American Airlines, even if they are operated by the later.
VictorFlew with Spirit AirlinesORD-LGAFeb 2025
Spirit landing at LGA makes life so easy to get to the city!
mauriceFlew with IberiaORD-JFKSept 2024
You should arrive early, take a lighht snack and be prepared for delays.
FreddyFlew with SouthwestMDW-LGAJuly 2024
On a stormy day, be prepare for delays.
AlexanderFlew with Spirit AirlinesORD-LGAMay 2024
Know your connection options — specially when LaGuardia Airport (LGA) only has buses going to/from the airport to the rest of the city. Luckily, the one to the subway station (Q70) is free-of-charge to ride on!

FAQs for booking flights from Chicago to New York

  • What is the fastest way to get from downtown Chicago to Chicago Midway Airport?

    A speedy way to get to from one airport to the other is using the Orange Line on the Chicago L Train system. The train runs to and from the Midway Transportation Center just east of the terminal building.

  • Are there any pet relief areas at Chicago O'Hare International?

    Chicago O'Hare International has four pet relief areas, three of which are outside and one that is located inside of the airport past the security checkpoint. The outdoor areas are located at Terminal 1, Terminal 2, and Terminal 5, while the indoor area is situated in Terminal 3.

  • What public transportation method is best to get from Downtown Chicago to Chicago O'Hare International?

    The Chicago Transit Authority Blue Line Train is the easiest way to get to the airport. The train runs 24 hours a day, and they offer more frequent service during morning and evening rush hour.

  • How can I get an Uber to Chicago O'Hare International?

    Just launch the app and request a ride from your location to be on your way to Chicago O'Hare International in no time. The cost of the trip will depend on your starting location and traffic conditions.

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

    In the last 3 days, the lowest price for a flight from Chicago to New York was $69 for a one-way ticket and $102 for a return.

  • Which airports will I be using when flying from Chicago to New York?

    Chicago is served by only 1 airport and there are 3 airports in New York. You will leave Chicago from Chicago O'Hare Intl and you will be arriving in New York at one of these airports: Newark, New York John F Kennedy Intl, or New York LaGuardia.

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

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

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

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

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

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

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

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

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

    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 Chicago to New York.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New York from Chicago 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 Chicago to New York?

    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 New York with an airline and back to Chicago with another airline.

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

    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 New York from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $66 or less one-way and $308 or less round-trip.
  • Before boarding United flights from Chicago to New York, passengers should stop in at the United Polaris Lounge located near gate C18 at Chicago O'Hare International. The Polaris Lounge has seating suites with pull-out tables that offer convenient power receptacles and USB charging ports. The lounge also features eight shower suites that have heated floors, and the staff will even press your clothes while you are freshening up. If you need to catch a nap before your flight, they have four daybeds available that come with earplugs and eye shades, plus a soothing sound generator. There is a buffet, a dining room, and a lounge to pass the time with great food and beverages before your flight.
  • If the whole family is making the trip to New York, stop by Kids on the Fly located in Terminal 2 just beyond the TSA checkpoints. This interactive exhibit delights children while also educating them. The play stations include an air traffic control tower, a giant helicopter powered by hand and foot pedals, and a small check-in counter with a working luggage scale, and a enormous cargo plane, complete with foam cargo boxes.
  • Passengers on flights from Chicago to New York departing out of Chicago Midway have a wealth of dining choices before their trip. Chicago sports legend Harry Caray's offers an array of steaks and chops, Woodgrain offers quick-service pizza options, and Tabo Sushi offers a variety of sushi favorites.
  • If you are looking for a meal before your flight from Chicago O'Hare International, there are choices aplenty. Wicker Park Seafood, located in the main hall of Terminal 2, offers a variety of sushi and seafood in their upscale lounge. The Publican Tavern is a great breakfast spot and is vegetarian friendly. If you are in the mood for Italian food, then Romano's Macaroni Grill, located in Terminal 3, has you covered.
  • You might not think of an airport as an excellent place to buy a new suit, but travelers that have some time before flights from Chicago to New York can stop in at Brooks Brothers, located in Terminal 3, Concourse H in Chicago O'Hare International. This location carries a full line of Brooks Brothers shirts, slacks, and suits to outfit you from head to toe.
See more tips

Prefer to fly direct from Chicago to New York?

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

Direct departures

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

Direct returns

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
See more direct flights

Top airline flying from Chicago to New York

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York. 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 Chicago to New York? 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 7941 reviews
6.6Boarding
5.0Entertainment
7.1Crew
5.1Food
5.9Comfort
Airline reviews

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

2.0 MediocreStephanie, Apr 2025ORD - LAX
Read more Spirit Airlines reviews

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

The seats were comfortable and not as tight as i would have expected. Would have been nice to be able to recline my seat, which was not available. Some form of free snacks and drink option would be appreciated as well, even just a water and small bag of crackers would have been better than nothing at all.

Bad seats. Very uncomfortable. Crew was fine. Too much upcsharging

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Fast check-in. Went through security quickly enough. Got their early. And the crew took care of my seating at the gate. The cost for 1 checked bag is ridiculous! $79!? Cmon!! The seating on the plane was very cramped, like sardines. I did not want to pay extra just to pick a seat. Might have to next time.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

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

Cabin class types available on flights from Chicago to New York

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

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