$115 Find Cheap Flights from Chicago to New York State - Compare and Save

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Cheap Flights from Chicago to New York

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
New York
New York1 stop$244
Buffalo
Buffalo1 stop$251
Albany
Albany1 stop$286
Syracuse
Syracuse1 stop$304
Rochester
Rochesternonstop$277
Ithaca
Ithaca1 stop$339
Binghamton
Binghamton1 stop$437
New York
New York1 stop$244
Buffalo
Buffalo1 stop$251
Albany
Albany1 stop$286
Syracuse
Syracuse1 stop$304
Rochester
Rochesternonstop$277
Ithaca
Ithaca1 stop$339
Binghamton
Binghamton1 stop$437
Booking Insights

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.

How much is a round-trip flight from Chicago to State of New York?

Flight prices are typical for this route right now.

Flights to State of New York from Chicago usually cost between $178 and $331 in November.
The lowest price found in the past 5 days was $246 on JetBlue (Nov 2-Nov 3).

What is the cheapest Chicago to New York State flight route?

The cheapest ticket to New York State from Chicago found in the last 5 days was to New York, at $199 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to New York LaGuardia Airport (LGA), and the cheapest round-trip airline ticket found on this route in the last 5 days was $238.

What is the cheapest time of day to fly to New York State?

The cheapest time of day to fly to New York State is generally at night, when round-trip flights cost $305 on average. Morning departures are around 24% cheaper than evening flights, on average. The most expensive time of day to fly to New York State is generally in the evening, which is peak travel time and where the average cost of a ticket is $400.

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $231 on average.

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

The cheapest month for flights from Chicago to New York State is January, when tickets cost $191 (return) on average. On the other hand, the most expensive months are September and June, when the average cost of round-trip tickets is $338 and $336 respectively.

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

For Chicago to New York State, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from New York State back to Chicago, the best deals are generally found on Wednesday, with Sunday being the most expensive.

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

To get a below average price on the flight from Chicago to New York State, you should book around 2 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

February

Cheapest flight

$115
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Albany

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

Insights shared by verified travelers who flew the route from Chicago to New York 
Verified travelerFlew with American Airlines-Apr 2026
travel to ohare is horror - work in extra time
mauriceFlew with Iberia-Sep 2024
You should arrive early, take a lighht snack and be prepared for delays.
AlexanderFlew with Spirit Airlines-May 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 - booking New York State flights

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

    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 State.

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

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

    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 from Chicago to New York State with an airline and back 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 State?

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

Reviews of the top 5 airlines serving from Chicago to New York

 
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.
7.9
SouthwestOverall score based on 4215 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It good. Just not that plane didn’t have power outlets to charge devices etc.

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

Good flight, regional jet so old and seats could use an upgrade

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

Long delays to board due to mechanical issues with plane.

Significant delays on my trip to Chicago and my trip back to NY

I almost missed my flight and they helped me out enormously

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Plane was delayed an hour causing me to miss my flight to London and now I am not arriving until Sunday instead of Friday. I am stranded at airport and they give me $12 of food vouchers. It's a joke and everyone I talked to was rude

it was a nightmare of a trip. multiple delays, dirty bathrooms, long wait in tarmac, ran out of fuel diverting flight. on and all over 4 hour delay!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

More options for your flight from Chicago to New York

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