$44 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 3/2. 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, 0 bags

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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Flight Deals

Cheap Flights from Chicago to New York

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New Yorknonstop$76
Buffalo
Buffalononstop$145
Syracuse
Syracuse1 stop$147
Albany
Albany1 stop$217
Rochester
Rochester1 stop$236
Ithaca
Ithaca1 stop$269
Binghamton
Binghamton1 stop$367
New York
New Yorknonstop$76
Buffalo
Buffalononstop$145
Syracuse
Syracuse1 stop$147
Albany
Albany1 stop$217
Rochester
Rochester1 stop$236
Ithaca
Ithaca1 stop$269
Binghamton
Binghamton1 stop$367

Book Cheap Chicago to New York Plane Tickets

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to New York

Thu, Apr 23 - Sat, Apr 25
Frontier Logo
6:31 am - 10:00 am
ORD
-
JFK
2h 29mnonstop
Frontier Logo
11:04 am - 1:00 pm
JFK
-
ORD
2h 56mnonstop
$76Frontier
Wed, Feb 25 - Tue, Mar 10
Spirit Airlines Logo
5:58 pm - 8:59 pm
ORD
-
LGA
2h 01mnonstop
Spirit Airlines Logo
7:40 am - 9:22 am
LGA
-
ORD
2h 42mnonstop
$77Spirit Airlines
Wed, Mar 18 - Sat, Mar 21
Frontier Logo
12:05 pm - 3:29 pm
ORD
-
JFK
2h 24mnonstop
Frontier Logo
4:29 pm - 6:29 pm
JFK
-
ORD
3h 00mnonstop
$77Frontier
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
2:35 pm - 5:55 pm
ORD
-
EWR
2h 20mnonstop
United Airlines Logo
9:25 pm - 11:13 pm
EWR
-
ORD
2h 48mnonstop
$99United Airlines
Sat, Mar 14 - Sat, Mar 21
American Airlines Logo
8:45 pm - 11:23 pm
ORD
-
BUF
1h 38mnonstop
American Airlines Logo
6:00 am - 7:14 am
BUF
-
ORD
2h 14mnonstop
$145American Airlines
Sat, Apr 25 - Sun, Apr 26
Southwest Logo
5:30 am - 8:30 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:25 am
LGA
-
MDW
2h 25mnonstop
$147Southwest
Wed, Mar 11 - Tue, Mar 17
JetBlue Logo
6:04 am - 12:45 pm
ORD
-
SYR
5h 41m
1 stop
JetBlue Logo
7:12 am - 11:25 am
SYR
-
ORD
5h 13m
1 stop
$147JetBlue
Fri, Jul 17 - Sun, Jul 19
American Airlines Logo
10:15 pm - 12:52 am
ORD
-
BUF
1h 37mnonstop
American Airlines Logo
6:10 am - 7:10 am
BUF
-
ORD
2h 00mnonstop
$165American Airlines
Wed, Jun 3 - Tue, Jun 9
JetBlue Logo
3:15 pm - 11:58 pm
ORD
-
SYR
7h 43m
1 stop
JetBlue Logo
6:00 am - 9:48 am
SYR
-
ORD
4h 48m
1 stop
$182JetBlue
Thu, Mar 5 - Sun, Mar 22
United Airlines Logo
7:05 am - 9:55 am
ORD
-
SYR
1h 50mnonstop
United Airlines Logo
6:25 am - 7:58 am
SYR
-
ORD
2h 33mnonstop
$209United Airlines
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.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to New York State from Chicago found in the last 72 hours was to New York, at $55 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 $89.

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.

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 $340 on average.

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 January, when tickets cost $160 (return) on average. On the other hand, the most expensive months are June and August, when the average cost of round-trip tickets is $237 and $237 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 Saturday, 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, which saves you about 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$44
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to New York John F Kennedy 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 
mauriceFlew with Iberia
ORD
-
JFK
Sep 2024
You should arrive early, take a lighht snack and be prepared for delays.
AlexanderFlew with Spirit Airlines
ORD
-
LGA
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.

  • 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 $229 on average. Morning departures are around 14% 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 $378.

Reviews of the 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 4284 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

bulkhead seat had very little legroom - even in bsiness class.

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.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

Flight got cancelled 1.5 hours prior to gate open and logistics of travel got delayed.

All of our flights were canceled, though every other airline was flying out and in

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Spirit cancelled my return flight the day before travel and so I had to book a last minute flight on American Airlines.

The counter people was very disrespectful screaming and not helpful to find another flight soon. Having to cancel the flight

Awful!!! Spirit cancelled my flight just 4 hours before departure- with no alternative flights available. I ended up missing a huge family gathering because I wasn’t able to get out. Such An awful experience. And on top of that, all the buckle and dime-ing for bags. I will never book with Spirit EVER

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

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.