NYC - CHI

₹ 4,356 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 11/6. 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 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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Cheap Flight Deals 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.

Recent return flight deals from New York to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly from New York to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Delta Logo
20:55 - 22:41LGA-ORD
2h 46mdirect
Delta Logo
18:55 - 22:17ORD-LGA
2h 22mdirect
₹ 11,700Delta
Find Deal
Sun, 25 May - Wed, 28 May
United Airlines Logo
21:35 - 23:16LGA-ORD
2h 41mdirect
United Airlines Logo
07:00 - 10:18ORD-LGA
2h 18mdirect
₹ 13,067United Airlines
Find Deal
Wed, 21 May - Wed, 28 May
Delta Logo
05:59 - 09:18EWR-ORD
4h 19m1 stop
Delta Logo
15:33 - 23:28ORD-EWR
6h 55m1 stop
₹ 13,409Delta
Find Deal
Sun, 25 May - Wed, 28 May
American Airlines Logo
07:00 - 08:53EWR-ORD
2h 53mdirect
American Airlines Logo
20:30 - 23:59ORD-EWR
2h 29mdirect
₹ 15,117American Airlines
Find Deal
Mon, 16 Jun - Tue, 17 Jun
Spirit Airlines Logo
11:55 - 23:29LGA-ORD
12h 34m1 stop
Spirit Airlines Logo
05:51 - 09:00ORD-LGA
2h 09mdirect
₹ 19,301Spirit Airlines
Find Deal
Fri, 6 Jun - Mon, 9 Jun
American Airlines Logo
07:19 - 09:01EWR-ORD
2h 42mdirect
American Airlines Logo
19:11 - 22:30ORD-EWR
2h 19mdirect
₹ 19,472American Airlines
Find Deal
Wed, 28 May - Thu, 29 May
Spirit Airlines Logo
05:00 - 06:37EWR-ORD
2h 37mdirect
Spirit Airlines Logo
21:28 - 00:46ORD-EWR
2h 18mdirect
₹ 19,899Spirit Airlines
Find Deal
Sat, 28 Jun - Sun, 29 Jun
Southwest Logo
06:25 - 12:45LGA-ORD
7h 20m1 stop
Southwest Logo
12:40 - 22:30ORD-LGA
8h 50m1 stop
₹ 19,985Southwest
Find Deal
Wed, 28 May - Thu, 29 May
Southwest Logo
06:00 - 15:00LGA-ORD
10h 00m1 stop
Southwest Logo
16:00 - 22:30ORD-LGA
5h 30m1 stop
₹ 20,241Southwest
Find Deal
Tue, 20 May - Tue, 20 May
Sun Country Air Logo
11:41 - 19:09EWR-ORD
8h 28m1 stop
Sun Country Air Logo
20:05 - 12:56ORD-EWR
15h 51m1 stop
₹ 25,194Sun Country Air
Find Deal
Fri, 9 May - Mon, 12 May

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 ₹ 7,628 and was between Newark Airport (EWR) 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 ₹ 7,628.

What’s the cheapest day of the week to fly from New York to Chicago?

The average price of all round-trip flights from New York to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from New York to Chicago, you should consider leaving on a Thursday and avoid Fridays if you are looking for the best rates. For your return to New York, you’ll find the best rates on Mondays and the most expensive ones on Wednesdays.

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 ₹ 15,031 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is ₹ 23,913 and ₹ 21,266 respectively.

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

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 ₹ 30,135, prices are generally cheapest when you fly direct.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

₹ 4,356
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly and prices are also 0% lower on average.
Flight from Newark Liberty Airport 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-MDWJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
AyeshaFlew with SouthwestLGA-MDWDec 2023
Great airports at both location. Always like flying southwest. Best airline.
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 ₹ 51 for a one-way ticket and ₹ 137 for a return.

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

    New York has 2 major airports: Newark and New York LaGuardia. Chicago O'Hare Intl is the only airport in Chicago. You’ll usually find the cheapest deals if you fly from Newark Liberty Airport.

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

    American Airlines, Delta, and JetBlue 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.

  • Which is the best airline for flights from New York to Chicago, American Airlines or Spirit Airlines?

    The two airlines most popular with KAYAK users for flights from New York to Chicago are American Airlines and Spirit Airlines. With an average price for the route of ₹ 21,541 and an overall rating of 7.2, American Airlines is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of ₹ 11,784 and an overall rating of 6.3.

  • 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.

See more FAQs

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 ₹ 10,547 or less one-way and ₹ 12,247 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.
See more tips

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 airlines 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.5Boarding
6.9Entertainment
6.5Food
7.2Comfort
8.0Crew
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

Our experience was not a good one. Our flight got cancelled and was not given any accommodations due to the inconvenience. We lost time on our vacation due to this inconvenience

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

I was traveling with my son and it was our first time with spirit so I didn’t realize our seats weren’t assigned. They scrambled and gave us seats next to each other. Also My son got sick on the plane and they really took care of him. Super family friendly crew and experience!

Great. I didn't eat or drink anything, nor did I have an option to be entertained, so i answered "okay"... but those categoriesreally don't apply. Everything else was great.

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

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

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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