Get data-powered insights and trends into flights from New York to Chicago to help you find the cheapest flights, the best time to fly and much more.
The cheapest return flight from New York to Chicago costs $118 on the route between Newark Airport (EWR) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 30% cheaper than other New York-Chicago routes. The most popular route is between New York LaGuardia Airport (LGA) and Chicago O'Hare Intl Airport (ORD).
Your flight ticket price will generally be cheaper if you fly to Chicago on a Saturday and more expensive on a Sunday. On your return trip to New York, you should consider flying back on a Friday, and avoid Sundays for better deals.
The cheapest month for flights from New York to Chicago is January, where tickets cost $199 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $352 and $306 respectively.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $317 on average.
In the past 5 days, the cheapest round-trip tickets from New York to Chicago were found on Delta ($192) and United Airlines ($192).
New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (180 flights per week), American Airlines (125 flights per week), and Delta (78 flights per week).
Weekly flights between New York and Chicago historically see delays in approximately 19% of cases, with the average delay over the past year being 158 minutes.
Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the evening have historically encountered delays more often.
Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Sunday has typically experienced more delays than other days.
Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 14% of their flights encountering any delays.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
Each day, there are between 49 and 67 nonstop flights that take off from New York and land in Chicago, with an average flight time of 2h 45m. The most common departure time is 7:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 449 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.
The average nonstop flight takes 2h 15m, covering a distance of 711 miles.
Early birds can take the earliest flight from New York at 5:30 am and will be landing in Chicago at 7:15 am.
If you prefer to fly at night, the latest flight from New York to Chicago jets off at 9:30 pm and lands at 11:00 pm.
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 | October |
| Cheapest flight | $98 |
Direct departures
New York to Chicago
Monday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Tuesday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Wednesday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Thursday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Friday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Saturday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Sunday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Direct returns
Chicago to New York
Monday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Tuesday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Wednesday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Thursday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Friday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Saturday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Sunday
American Airlines,Delta,JetBlue, +2 more
American Airlines,Delta, +3 more
1
2
Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.
Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.
The flight was smooth. The Southwest experience has degraded overall, but this one was okay.
The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.
no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.
For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.
Great flight. I didn't get a drink because I was asleep whole on the flight.
Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.
WiFi was not working and didn’t have a beverage service
All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous
My bag was damaged and is now missing a wheel. I tried to buy a claim in on the website but it would not accept my confirmation # for submission. Other than that, everything else was good!
It was as good as it could be. Flying is not a pleasant experience these days.
There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.
Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors
Got on the plane and sat there for an hour before departure.
Cramped seating for me. Luckily it wasn’t a long flight
5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.
I usually have a positive experience with Delta. Complimentary upgrades are always nice!
long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.
The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.
The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.
1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding
Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time
Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.
3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.
Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.
There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.
Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done
The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.
The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure
Their app did not recognize my Aeroplan frequent flyer number and would not allow me access to my boarding card. Ground staff was readily available at the airport to print it out to me.
The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.
Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport
There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.
It was good experience this time. The flight was on time.
The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.
My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end
The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.
Extreme weather delays. Missed my flight to France and I ended up leaving the plane.
Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.
I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.
Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy
The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve
Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.
This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.
The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company
Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.
Severe turbulence. Captain never came on to reassure passengers after things settled down.
We were delayed three times ,and that destroyed my plans, and reservations
The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew
The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $613 | 2h 15m |
| Trains | $350 | 21h 36m |
| Buses | $113 | 15h 49m |