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 | $54 |
Direct departures
New York to Chicago
Monday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Tuesday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Wednesday
American Airlines, Delta, Frontier, +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, Frontier, +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, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Wednesday
American Airlines, Delta, Frontier, +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, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Sunday
American Airlines, Delta, Frontier, +4 more
American Airlines, Delta, +5 more
3
4
Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.
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.
Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.
WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.
WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.
The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.
All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous
Got on the plane and sat there for an hour before departure.
They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.
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
United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.
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
We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.
Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude
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.
Everything was good. On time, boarding fast, flight attendants friendly.
Spirit has always and will always stink. Absolute worst airline around.
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.
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.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $520 | 2h 25m |
| Trains | $206 | 21h 00m |
| Buses | $200 | 20h 42m |