When flying from New York to Chicago, the cheapest days to fly are generally Tuesdays, while the cheapest months are typically January and February.
Cheapest Route: Opt for flights between JFK, EWR or LGA and ORD for the cheapest fares.
Booking Advance: Book your flight at least 160 days in advance for the best prices.
Budget Airline: Consider flying with Spirit Airlines, as they generally offer the cheapest fares.
Layovers: Flights with one stop are typically cheaper than direct flights.
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 | January |
|---|---|
High season | October |
Cheapest flight | $30 |
Find which airlines fly direct from New York to Chicago, which days they fly and book direct flights.
Nonstop departures
Monday
ANA, Air Europa, Air France, +28 more
ANA, Air Europa, +29 more
27
28
Tuesday
ANA, Air Europa, Air France, +28 more
ANA, Air Europa, +29 more
27
28
Wednesday
ANA, Air Europa, Air France, +27 more
ANA, Air Europa, +28 more
26
27
Thursday
ANA, Air Europa, Air France, +27 more
ANA, Air Europa, +28 more
26
27
Friday
ANA, Air Europa, Air France, +27 more
ANA, Air Europa, +28 more
26
27
Saturday
ANA, Air Europa, Air France, +26 more
ANA, Air Europa, +27 more
25
26
Sunday
ANA, Air Europa, Air France, +29 more
ANA, Air Europa, +30 more
28
29
Nonstop returns
Monday
ANA, Air Europa, Air France, +32 more
ANA, Air Europa, +33 more
31
32
Tuesday
ANA, Air Europa, Air France, +30 more
ANA, Air Europa, +31 more
29
30
Wednesday
ANA, Air Europa, Air France, +32 more
ANA, Air Europa, +33 more
31
32
Thursday
ANA, Air Europa, Air France, +31 more
ANA, Air Europa, +32 more
30
31
Friday
ANA, Air Europa, Air France, +30 more
ANA, Air Europa, +31 more
29
30
Saturday
ANA, Air Europa, Air France, +32 more
ANA, Air Europa, +33 more
31
32
Sunday
ANA, Air Europa, Air France, +31 more
ANA, Air Europa, +32 more
30
31
The WiFi has been awful on my last few Delta Air Lines flights.
The WiFi has been awful on my last few Delta Air Lines flights.
Only one side of the heafphone jack work. Crew was friendly and helpful.
It was reported to the passengers that Delta failed to schedule the crew properly. This error caused the pilot to show up about 30 minutes late. All in all Delta's inability to take care of this basic function resulted in about an hour delay.
Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …
5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.
Older plane and it came with Fleas and flea bites!
All good on Delta's part. Passengers could be a little more courteous to each other.
The fight was about 2 1/2 hours delayed, but that was weather related. The flight was also overbooked. But we were in Comfort plus so the flight was fine for us.
Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours
I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.
Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.
The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.
In flight on demand didn't work at our seats. Only a single beverage/snack run.
Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.
I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.
Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app
Kayak sent over to jet blue my account being Mike Callaghan instead of Michael. I have a jet blue account with Michael that was connected
The flight was excellent. The crew was welcoming and attentive.
Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.
There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.
Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done
Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA
As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.
The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.
when you can say you don't remember being at any point upset during a flight, the airline is winning .
The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.
It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!
Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.
Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.
Some sort of compensation for missing work because of a cancelled flight that was United’s fault
Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.
3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed
My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.
The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.
This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.
Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.
the food choice of packaged chips and popcorn was utterly ridiculous for first class
Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the
Late and next flight even later. Who leaves at 245 am and arrives at 330 am ? No wifi, 4 hr flight and one bag of pretzels? AA should be ashamed
No problems on this flight. Entertainment system worked well. On time take off and arrival. Smooth most of the way.
The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.
The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.
Customer service. There is no way to call them and online chat doesn't deal with your specific concerns. I don't plan to fly spirit again.
Better overall experience from my first flight with Spirit several years ago. Efficient boarding (albeit I arrived after all rows were called) and flight actually left earlier than planned. I am still baffled by being charged for everything, even a non-alcoholic beverage. And there is definitely less seat room which makes a flight that’s more than 2 hours really uncomfortable.
Would have been better if I would’ve made it on my flight but it was delayed twice and then canceled and now I’m stuck till Monday which was and extra 5 days I did not count on .
You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.
Both flights were delayed. Flight from LGA to DTW caused serious anxiety as 3 people were removed from the aircraft before take off for disorderly conduct. Extremely uncomfortable to be in that situation. Staff handled themselves okay- definitely could’ve been more professional and deescalated the situation first. No apology for the delays at all. No water, no snack, no nothing. Not a good flight experience.
Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.
The flight was minimally delayed and after landing we needed to wait an hour, hungry, thirsty, and with other customers improper behavior. Flight was good and quick, boarding was delayed but quick. Thanks
Overall, poor. Boarding was extremely slow, which caused flight delays.
| Average price | Average duration | |
|---|---|---|
| Flights | $516 | 2h 30m |
| Trains | $170 | 21h 39m |
| Buses | $228 | 22h 42m |