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 | $78 |
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
I'm glad it wasn't only 75% full because I could get a good seat
I'm glad it wasn't only 75% full because I could get a good seat
if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.
Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.
Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.
Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.
Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.
The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.
no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.
First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.
Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.
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.
I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.
I am still at the Airport! Delayed Delayed and Delyaed
Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow
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.
newer aircraft, ability to connect my headset via blue tooth for entertainment.
Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5
Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.
It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.
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.
The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.
I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.
Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.
The staff are very, very professional. It's what flying should feel like.
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
Delays with no explanation. It could have been handled better.
Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!
My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket
Shut down without prior notice End up with spending lots of extra $$$
My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S
That this is my second time the they cancel flights and they always wait until the last minute to let people know
Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.
Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.
Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.
Like Spirit but bad that you have to pay for water 🙃
If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.
For a change, friendly staff at check-in and in flight.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $508 | 2h 20m |
| Buses | $209 | 22h 36m |