Spirit's Big Front Seat offers 20-inch width and 11 inches more legroom.
Spirit's Wi-Fi offers gate-to-gate connectivity across all routes.
Planning a trip from Chicago to New York? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
When booking a flight from Chicago to New York, it's generally cheapest to fly on a Tuesday in February. This could help you save money on your trip.
Day of Week: Choose to fly on a Tuesday for the cheapest fares.
Booking Advance: Book your flight at least 180 days in advance to get the best deal.
Cheapest Airline: Consider flying with Spirit Airlines, which generally offers the cheapest fares.
Route Selection: The route from Chicago O'Hare (ORD) to New York LaGuardia (LGA) is typically the cheapest.
Direct or Layover: It's cheaper to fly direct, despite common misconceptions.
This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK.
Low season | February |
---|---|
High season | November |
Cheapest flight | $42 |
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
2
3
Tuesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Wednesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Thursday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Friday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Saturday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Sunday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Direct returns
New York to Chicago
Monday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Tuesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Wednesday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Thursday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Friday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Saturday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Sunday
American Airlines, Delta, JetBlue, +3 more
American Airlines, Delta, +4 more
2
3
Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.
Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.
We sat on the plane on the tarmac for 4 hours.
I'm not a fan of Southwest's model. I don't like the herding style of boarding.
Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.
Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.
Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.
It is southwest seat was ok. Not the most comfortable seat
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
Plz don't take away free bags and free seating
Boarding was tough as we had to take a bus out to the plane and walk up a lot of stairs. Difficult with heavy carry-ons that said I got an entire empty row of seats, which was excellent for an international flight. Food was very mediocre but happy with the comfort so not complaining.
After I checked in, I realized we had no seat assignment. It said they would be assigned at the gate. This was really frustrating because I usually use a lounge before flights, but I couldn't because I had to be at the gate to ensure we got our seat assignments. The gate agent arrived an hour before the flight left. I was the first one up to ask about seat assignments. She told us to wait for names to be called. Dozens of other passengers were paged, but we were not. Finally, I asked my husband to ask. He went up and was also told to wait. About 10 minutes later, they called for boarding. We still had not been told our seats. We went back to the desk and they were in a panic, saying we actually weren't on that flight. Then they made an announcement telling the stand by passengers to not board (in case we needed their seats). It was so stressful and unprofessional. Finally they gave us our seats. I have no idea what happened and why the two desk agents seemed to have conflicting ideas about our seats, whether we were on that flight etc.
Subject: Complaint Regarding Disrespectful Behavior by Delta Air Lines Staff at Boarding Gate Dear Delta Air Lines Team, I am writing to formally file a complaint regarding the behavior of a staff member at the boarding gate today, May 14, 2025, at Las Américas International Airport. While we were preparing to board flight DL-1829 to New York, scheduled for 2:28 PM at gate T-11, we were informed that the aircraft was experiencing water system issues and that passengers were advised to use the restroom before boarding. I politely approached one of the Delta staff members to ask whether the lavatory would be partially or completely unavailable during the flight, as I am traveling with a baby in my arms. The employee’s response was extremely rude and arrogant. He replied, in an unnecessarily hostile tone, something along the lines of: “It’s either that or we cancel the flight — do you want us to cancel the flight?” This response lacked any empathy or professionalism. I understand that technical issues can arise, but that does not excuse such inappropriate treatment of passengers. I felt deeply disrespected and disappointed by the interaction. I sincerely hope appropriate measures are taken, and that all staff members receive the necessary training to treat passengers with courtesy, especially in delicate situations like this one.
This is speaking of the original flight leaving on April 30th(DL 1957) not the rebooked the following morning DL 9887. On April 30th, it was unusually crowded at Sangster International Airport (MBJ) the morning my mother and I arrived for our flight. She had to exceedingly long time for a wheelchair, once a wheelchair attendant arrived to take us to thru immigration and security then to go to gate the flight was boarding. We stayed on board for 3 1/2 hrs until the flight crew notified the passengers that flight indefinitely delayed so we had to stay by gate area. Before that my mom had to wait an additional 20-30 mins to deboard the plane. Was given food vouchers, by the time I came back the gate agents said the flight was gonna to reboard, so all the wheelchair passengers lined up. We waited an additional 45 mins, while I received a notification from kayak that the flight was cancelled. And on my delta app updated that flight was being detoured to Miami then from Miami back to JFK. We boarded the plane started to eat, then the flight crew notified us the flight was indeed being detoured & that how come the gate agents didn’t notified the passengers. We stayed on board for another 30-40 mins then was told by the captain that they tried all avenues to get the passengers back to JFK but the crew couldn’t continue the journey and the flight was cancelled. So we deboarded the plane again. Was told that we were going to be setup in hotels for the night. The hotel that we setup to go to wasn’t suitable for my mother’s needs and requested one nearby we were located in Jamaica. So any we had called a taxi to come to take us back where we stayed in Jamaica, that we had to pay out of own pockets.
Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.
third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta
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
Everything was ok!! Just bags came up a little be late.
I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.
The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!
Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.
A bit rush for transit. Food and entertainment are not available
Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.
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.
Whenever a passenger purchase a ticket his advantage number should automatically to his information. It's not everyone remember the number. You request for your number and American airline agent say they will email it....and they never email anything and you loose your mileage just because you don't remember your number. It should automatically go your information and associate with your email account at all times
The flight was two hours late to take off. The captain kept making announcements in English, but the volume on the speakers was low and we could not hear him. The flight attendant’s French translation was loud and clear, but we couldn’t understand French. The crew was nowhere to be found to relay what the captain was announcing. Very frustrating experience. American has to do better.
Paid $35 and not able to access the internet at all.
Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time
Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay
Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.
You ant watch TV if you don't have a device, the seats have more space, and the snacks are different.
Flight was empty so had a whole row to myself. Still had to wait to get the bag due to the negligence at Palm Springs departure.
Amazingly comfy flight - I had upgraded for a reasonable price and it was worth it. The food also was good.
Random carry-on baggage inspection before boarding for NO REASON. The crew kept talking loudly the entire time, making it impossible to rest. When I asked the crew for something, they said they would come back later but never did. It was an EXTREMELY UNPLEASANT and UNCOMFORTABLE flight.
Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔
All was good expecting the seats need a bit of cushion. Besides that I can’t complain.
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.
Transportation mode | Average price | Average duration |
---|---|---|
Flights | $926 | 2h 00m |
Trains | $246 | 21h 55m |
Buses | $193 | 20h 36m |
Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.