Planning a trip from New York to Chicago? 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 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.
AI-powered; AI can make mistakes.
| Low season | January |
|---|---|
| High season | May |
| Cheapest flight | $57 |
Direct departures
New York to Chicago
Monday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Tuesday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Wednesday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Thursday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Friday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Saturday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Sunday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Direct returns
Chicago to New York
Monday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Tuesday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Wednesday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Thursday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Friday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Saturday
American Airlines, Delta, JetBlue, +4 more
American Airlines, Delta, +5 more
3
4
Sunday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous
All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous
Everything went smoothly and we even arrived a little bit early.
Great vacation. Can't wait till next year for another one.
Great flight but super high price. Glad it was a business trip and not personal
On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane
The seats were comfortable, and the boarding process was pretty smooth.
3 hour delay. Had to change plans and was still delayed.
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.
Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.
It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.
The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.
It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.
The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.
Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)
My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.
Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗
I truly love flying with Delta. They have always treated me with the upmost respect
The flight was great. The gate location was way to far away!!!
Cramped seating for me. Luckily it wasn’t a long flight
Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.
It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.
Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.
The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.
Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.
They did the one thing that really matters - got to Chicago early.
The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect
It was nice to have gotten up upgraded to first class with a meal on a three hour flight
Very bad! They kept delaying my flight and wouldn’t do anything about it
Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.
Pilot navigated severe weather/snow storm with skill. Described his intentions clearly
Little warm on the plane and delayed for an hour
So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute
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.
Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative
I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable
It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.
It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.
After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.
Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.
Not seat assigned because overbooking. We could go because some people decided to give their seats.
The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.
Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.
A bottled or canned drink, whether water or soda would have been appreciated upon settling in and flying, without being charged for it.
spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.
Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.
I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.
Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.
Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.
Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $649 | 2h 30m |
| Trains | $225 | 21h 05m |
| Buses | $201 | 20h 31m |