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, 28% 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 Tuesdays 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 May, where the average cost of round-trip tickets is $319 and $302 respectively.
No, with an average price for the route of $324, prices are generally cheapest when you fly direct.
In the past 5 days, the cheapest round-trip tickets from New York to Chicago were found on Southwest ($184) and JetBlue ($185).
New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (186 flights per week), American Airlines (126 flights per week), and Delta (84 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 159 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 55 and 69 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 463 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 5:11 am and will be landing in Chicago at 6:59 am.
If you prefer to fly at night, the latest flight from New York to Chicago jets off at 9:40 pm and lands at 11:30 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 | June |
| Cheapest flight | $94 |
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
It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!
It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!
Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.
Kayak could’ve posted the correct gate number. Almost missed my flight.
Slow boarding, limited food and drink portions. Bad delays and turbulence
there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!
OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.
Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!
Was fine, delayed and feels like southwest is always late
I don't know why flying out of Sarasota requires two plane changes.
The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.
On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.
I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.
Was revoked with Jet Blue due to delay from Kenya Air
WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.
Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,
WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.
The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!
Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.
my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful
This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.
Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats
Boarded early, left early, arrived 40 mins early! A win win for me!
These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.
This flight is a quick way to get to Chicago, but a bit expensive.
O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.
Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.
Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.
boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.
The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.
The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.
The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.
The flight from LA to Chicago was smooth and service was very good overall.
The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response
Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.
They lost my baggage and I am still struggling to the information and update
Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.
The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.
It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.
Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!
The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.
There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.
The staff at the check in counter was so rude. Made you feel Incompetent
Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.
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
Plane was hot and miserable and the crew was rude!
12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink
They didn’t offer a water, even after I asked
They switched our terminal 3 times and we were delayed for four plus hours!!!
It was an early flight and most people napped/slept and the crew let us which was nice.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $570 | 2h 20m |
| Trains | $251 | 21h 27m |
| Buses | $132 | 16h 01m |