CHI

Find Business Class Flights from New York to Chicago

1 adult
1 adult, Business, 0 bags

KAYAK searches hundreds of travel sites at once for business 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 Business 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 business class round-trip flight deals to Chicago

Mon, Jun 8 - Wed, Jun 10
American Airlines Logo
5:11 am - 6:59 am
EWR
-
ORD
2h 48mnonstop
American Airlines Logo
8:20 pm - 11:38 pm
ORD
-
EWR
2h 18mnonstop
$422American Airlines
Tue, Jun 9 - Thu, Jun 11
American Airlines Logo
7:57 am - 10:05 am
JFK
-
ORD
3h 08mnonstop
American Airlines Logo
5:10 am - 11:27 am
ORD
-
JFK
5h 17m
1 stop
$446American Airlines
Thu, Jun 25 - Fri, Jun 26
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
$449American Airlines
Tue, Jun 9 - Thu, Jun 11
American Airlines Logo
2:49 pm - 10:00 pm
JFK
-
ORD
8h 11m
1 stop
American Airlines Logo
5:10 am - 11:27 am
ORD
-
JFK
5h 17m
1 stop
$456American Airlines
Mon, Jun 8 - Wed, Jun 10
American Airlines Logo
1:59 pm - 3:55 pm
JFK
-
ORD
2h 56mnonstop
American Airlines Logo
6:04 am - 1:29 pm
ORD
-
JFK
6h 25m
1 stop
$460American Airlines
Thu, Jun 25 - Fri, Jun 26
American Airlines Logo
5:01 pm - 9:33 pm
JFK
-
ORD
5h 32m
1 stop
American Airlines Logo
1:19 pm - 10:14 pm
ORD
-
JFK
7h 55m
1 stop
$466American Airlines
Mon, Jun 8 - Wed, Jun 10
American Airlines Logo
2:49 pm - 7:53 pm
JFK
-
ORD
6h 04m
1 stop
American Airlines Logo
8:00 am - 3:59 pm
ORD
-
JFK
6h 59m
1 stop
$470American Airlines
Tue, Jun 9 - Thu, Jun 11
American Airlines Logo
6:25 am - 8:08 am
LGA
-
ORD
2h 43mnonstop
American Airlines Logo
6:59 am - 10:10 am
ORD
-
LGA
2h 11mnonstop
$470American Airlines
Mon, Jun 15 - Wed, Jun 17
Frontier Logo
10:00 pm - 8:03 am
LGA
-
ORD
11h 03m
1 stop
Frontier Logo
1:29 pm - 8:58 pm
ORD
-
LGA
6h 29m
1 stop
$491Frontier
Wed, Aug 5 - Sat, Aug 8
Frontier Logo
10:29 pm - 7:53 am
EWR
-
ORD
10h 24m
1 stop
Frontier Logo
1:50 pm - 1:03 am
ORD
-
EWR
10h 13m
1 stop
$501Frontier

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

Low seasonJanuary
Average price round-trip$976
Good deal round-trip$830
Good deal one-way$406
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 2% lower on average.
(avg. price over the last 2 weeks)
or less
or less

When to book business class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for business 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 Business 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 business 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 Thursday when prices are cheapest and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Monday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly Business 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 Business Class flights from New York to Chicago is February, where tickets cost $528 (round-trip) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $1,316 and $927 respectively.

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

There are 3 airlines that fly Business Class from New York to Chicago. They are: American Airlines, Delta and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at $379 for a round-trip flight. On average, the best prices for flying Business Class on this route can be found at American Airlines.

FAQs for Business Class New York to Chicago Flights

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

    The price of a business 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 $914 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 business class between New York and Chicago?

    The highest-rated airline by KAYAK users offering business class flights for this route is Southwest, with an overall rating of 7.9.

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

  • What’s a good price for a business class ticket between New York and Chicago? 25% of our users found flights on this route for $359 or less one-way and $724 or less round-trip.
  • Look for a flight with a layover if you’re looking to save, as direct business class flights are generally more expensive for the route.

Reviews of the Top 5 Airlines Flying Business 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 business 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.
7.9
SouthwestOverall score based on 4264 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
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.

My service light was on 15 minutes before I had to get up and find a glass of ice. And I was in business class. The meals were not for either my wife and I. She did not eat the entire 10 hour flight and I managed a bowl of soup. I was expecting much more from business with what we paid.

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

My business class seat was inoperable and unable to recline for 10 hour flight.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

Landed without a gate ready. Plane is extremely old and dirty.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

The tray table was broken and the food was terrible.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

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

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.

On time departure and early arrival. Flight attendant very nice.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

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.

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

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.

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.