Economy Plus provides extra legroom, enhancing comfort on short flights.
Priority Boarding in Zone 2 helps avoid gate-checking carry-ons.

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.
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 | November | 
| Cheapest flight | $64 | 
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
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
Full cans of soda would be nice. A choice between two snacks would be appreciated.
Tried watching free movie and it kept freezing so I couldn’t finish.
All was good. I just had a hard time getting connected to the WiFi/internet during the flight
Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.
Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.
Delays delays delays. Late taking off, late landing, wait for a gate, etc.
Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.
I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.
Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay
The flight was great. The gate location was way to far away!!!
Cramped seating for me. Luckily it wasn’t a long flight
This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one
I believe that a four-hour trip should have a meal. Delta had none.
Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.
Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had
At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.
Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.
My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.
The entertainment and wifi mostly didn't work on this flight.
Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.
Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.
After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.
Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.
Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍
Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.
Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!
See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.
Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.
Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.
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.
This was the best 2 flights I have had with American out of SGF. Great crew both flights.
Excellent - explanations were clear staff was nice and flight was comfortable
Lost bag and 2 days no word leaving for cruise no clothes or stuff
Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.
Food was ok, but not as good as I have had before on AA.
Pretty good. The food was just mediocre, the boarding and crew were good.
Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.
Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.
Great experience for my first time on Spirit. Wey clean plane, great staff, very smooth. Gave food and entertainment “poor” simply because there was no option for NA….i did not get food nor did I order WiFi….so not a fair assessment but neither would giving top marks without experiencing. Overall, great experience.
We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.
Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.
Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.
Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.
The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.
As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.
Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.
| Transportation mode | Average price | Average duration | 
|---|---|---|
| Flights | $616 | 2h 30m | 
| Trains | $281 | 20h 59m | 
| Buses | $197 | 20h 21m | 
Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.