CHI

Find First Class Flights from New York to Chicago

1 adult
1 adult, First, 0 bags

KAYAK searches hundreds of travel sites at once for first class flights from New York to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, as well as popular online travel agencies
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Cheap First Class Flight Deals from New York to Chicago

 
These are the cheapest deals for flights from New York to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent first class round-trip flight deals to Chicago

Tue, Jul 21 - Thu, Jul 30
American Airlines Logo
5:30 am - 7:15 am
EWR
-
ORD
2h 45mnonstop
American Airlines Logo
8:09 pm - 11:30 pm
ORD
-
EWR
2h 21mnonstop
$415American Airlines
Sun, Jul 26 - Tue, Jul 28
American Airlines Logo
5:30 am - 7:15 am
EWR
-
ORD
2h 45mnonstop
American Airlines Logo
8:09 pm - 11:30 pm
ORD
-
EWR
2h 21mnonstop
$419American Airlines
Mon, Nov 23 - Wed, Nov 25
Delta Logo
10:50 am - 12:36 pm
JFK
-
ORD
2h 46mnonstop
Delta Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
$424Delta
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
8:27 am - 10:30 am
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
4:30 pm - 8:01 pm
ORD
-
JFK
2h 31mnonstop
$425American Airlines
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
5:23 am - 7:13 am
EWR
-
ORD
2h 50mnonstop
American Airlines Logo
6:44 am - 10:04 am
ORD
-
EWR
2h 20mnonstop
$433American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
8:27 am - 10:30 am
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
8:10 am - 1:59 pm
ORD
-
JFK
4h 49m
1 stop
$441American Airlines
Tue, Jun 9 - Wed, Jun 10
American Airlines Logo
5:11 am - 6:59 am
EWR
-
ORD
2h 48mnonstop
American Airlines Logo
6:51 am - 10:02 am
ORD
-
EWR
2h 11mnonstop
$441American Airlines
Fri, Jul 10 - Sat, Jul 11
American Airlines Logo
5:30 am - 7:15 am
EWR
-
ORD
2h 45mnonstop
American Airlines Logo
8:09 pm - 11:30 pm
ORD
-
EWR
2h 21mnonstop
$442American Airlines
Fri, Aug 7 - Sun, Aug 9
American Airlines Logo
5:29 am - 7:15 am
EWR
-
ORD
2h 46mnonstop
American Airlines Logo
6:43 am - 10:02 am
ORD
-
EWR
2h 19mnonstop
$446American Airlines
Mon, Jul 6 - Wed, Jul 8
Delta Logo
3:00 pm - 5:11 pm
JFK
-
ORD
3h 11mnonstop
Delta Logo
10:00 am - 1:20 pm
ORD
-
JFK
2h 20mnonstop
$457Delta

Good to Know - First Class Flights from New York to Chicago

Average price round-trip$704
Good deal round-trip$598
Good deal one-way$421
Most popular time to fly with an average 11% increase in price.
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, so you can find the best time to fly.
Average price per month
Flight prices as travel date approaches

KAYAK’s Insights & Trends for New York to Chicago First Class Flights

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.

What’s the cheapest day of the week to fly first class from New York to Chicago?

The average price of all flights from New York to Chicago clicked on KAYAK for each day over the last 12 months.

Look for departures on Saturday when prices are cheapest and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Chicago, Tuesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly First Class from New York to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New York to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for First Class flights from New York to Chicago is January, where tickets cost $507 (round-trip) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $883 and $730 respectively.

Which airlines offer First Class tickets between New York and Chicago?

There are 3 airlines that fly First Class from New York to Chicago. They are: Delta, American Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Delta at $377 for a round-trip flight. On average, the best prices for flying First Class on this route can be found at American Airlines.

FAQs for First Class New York to Chicago Flights

  • How much is a first class ticket from New York to Chicago?

    The price of a first class flight ticket between New York and Chicago depends on many factors, like when the ticket was booked, the departure date, season and much more. The average price for all bookings made on KAYAK for this route over the last 2 weeks is $717 for a round-trip.

  • Is it cheaper to fly business or first class between New York and Chicago?

    Business Class tickets are usually cheaper, but that's not the case for this route, with an average return fare of $914, compared to $717 for First Class.

  • What is the best airline when flying first class between New York and Chicago?

    The highest-rated airline by KAYAK users offering first class flights for this route is Southwest, with an overall rating of 8.0.

KAYAK's Tips for Finding Cheap First Class Flights from New York to Chicago

  • What’s a good price for a first class ticket between New York and Chicago? 25% of our users found flights on this route for $404 or less one-way and $649 or less round-trip.
  • Try flying direct if you’re looking to save, as direct first class tickets are cheaper on average.

Reviews of the Top 5 Airlines Flying First Class from New York to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from New York to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly first class to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4262 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

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.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

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.

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.

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.

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.

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.

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.

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 $$$

It was a full Spirit experience. Got to witness police officers having to deboard a passenger and cost us about an hour of delay. Front seat was spacious and better than expected.

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.

Everything you need to know for your flight to Chicago

Cabin class types available on flights from New York to Chicago

Cabin classes available on flights from New York to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.