$33 Find Cheap Flights from Chicago to New York State

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 4/29. 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 State

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York State.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York State.
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Best New York Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

New York
New Yorknonstop$63
Buffalo
Buffalo1 stop$158
Syracuse
Syracuse1 stop$189
Rochester
Rochester1 stop$193
Albany
Albanynonstop$225
Ithaca
Ithaca1 stop$249
Binghamton
Binghamton1 stop$417

Cheap Flight Deals from Chicago to New York (CHI-USNY)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 round-trip flight deals from Chicago to New York

Recommended round-trip deals departing in the coming months 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
5:55 am - 9:00 amORD-LGA
2h 05mnonstop
Spirit Airlines Logo
4:38 pm - 6:17 pmLGA-ORD
2h 39mnonstop
$63Spirit Airlines
Find Deal
Thu, May 1 - Tue, May 6
Spirit Airlines Logo
5:55 am - 9:00 amORD-LGA
2h 05mnonstop
Spirit Airlines Logo
4:38 pm - 6:17 pmLGA-ORD
2h 39mnonstop
$64Spirit Airlines
Find Deal
Thu, May 1 - Tue, May 6
Delta Logo
7:00 am - 10:25 amORD-JFK
2h 25mnonstop
Delta Logo
8:00 am - 9:51 amJFK-ORD
2h 51mnonstop
$153Delta
Find Deal
Tue, May 20 - Tue, May 27
American Airlines Logo
4:44 pm - 8:00 pmORD-JFK
2h 16mnonstop
American Airlines Logo
9:00 am - 11:09 amJFK-ORD
3h 09mnonstop
$154American Airlines
Find Deal
Wed, May 21 - Tue, May 27
Delta Logo
7:10 am - 10:29 amORD-JFK
2h 19mnonstop
Delta Logo
11:18 am - 1:10 pmJFK-ORD
2h 52mnonstop
$157Delta
Find Deal
Wed, Apr 16 - Sat, Apr 19
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
$157Southwest
Find Deal
Wed, Apr 16 - Sun, Apr 20
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
Southwest Logo
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$158Southwest
Find Deal
Tue, May 27 - Fri, May 30
American Airlines Logo
4:44 pm - 8:00 pmORD-JFK
2h 16mnonstop
American Airlines Logo
3:55 pm - 5:34 pmJFK-ORD
2h 39mnonstop
$162American Airlines
Find Deal
Sat, May 17 - Sat, May 24
United Airlines Logo
6:05 pm - 11:30 pmORD-LGA
4h 25m1 stop
United Airlines Logo
6:25 am - 8:00 amLGA-ORD
2h 35mnonstop
$183United Airlines
Find Deal
Sat, May 3 - Sun, May 4
United Airlines Logo
9:24 pm - 12:45 amORD-EWR
2h 21mnonstop
United Airlines Logo
9:55 pm - 11:37 pmEWR-ORD
2h 42mnonstop
$193United Airlines
Find Deal
Fri, Jul 18 - Mon, Jul 21

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 State 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 State.
The cheapest ticket to New York State from Chicago found in the last 72 hours was to New York, at $88 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 72 hours was $88.

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

The average price for all round-trip flights from Chicago to New York State depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to New York State is generally at night, when round-trip flights cost $254 on average. Morning departures are around 3% cheaper than evening flights, on average. The most expensive time of day to fly to New York State is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $363.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $686, prices are generally cheapest when you fly direct.

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

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 State, 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 State is September, when tickets cost $154 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $250 and $248 respectively.

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

The average price of all round-trip flights from Chicago to New York State clicked on KAYAK for each day over the last 12 months.
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 Tuesday, with Sunday being the most expensive.

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

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 State, 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 State, 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

Cheapest flight

$33
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to New York LaGuardia Airport

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 
VictorFlew with Spirit AirlinesORD-LGAFeb 2025
Spirit landing at LGA makes life so easy to get to the city!
mauriceFlew with IberiaORD-JFKSep 2024
You should arrive early, take a lighht snack and be prepared for delays.
FreddyFlew with SouthwestMDW-LGAJul 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 - 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.

See more FAQs

Top 5 airlines serving from Chicago to New York

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York State. 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.
8.0
SouthwestOverall score based on 4274 reviews
7.6Entertainment
8.2Boarding
8.6Crew
7.1Food
8.0Comfort
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

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.

WiFi on the flight was not working. Thus, entertainment options were limited.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

My Flight was cancelled and there was no other options available for me to Travel on that date and my options for the next day was all connecting flights that would have me in the airports all day before reaching my destination

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

I know it was not in Deltas fault. But numerous delays and cancelations. I requested a hotel voucher and was told they weren't available. The lady on my hotel shuttle did receive one from American. Why the difference?

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

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.

Everything on the flight was OK. However, the price is very deceiving the way that it is marketed. It seems like it’s going to be very low cost, but when you add in the charges for luggage, choosing a seat, food & drink, etc., that are already included in other competitors fares, it really is no cheaper, and possibly even more expensive than the other carriers. It actually makes your carrier seem dishonest.

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!!!

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

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.

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

Cabin class types available on flights to New York

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

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