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Cheap First Class Flights from New York to Chicago

NYC — CHI
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, First
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Essential info for First Class flights from New York to Chicago

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data were last updated on July 16, 2026.

Top Rated Airline

American Airlines

No. of Airlines

4

Arrival Airport

Chicago O'Hare Intl Airport
Most popular airline to fly first class with to Chicago in the past 7 days
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Airlines that offer first class options for this route
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Closest airport for this route
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Find First Class flight deals from New York to Chicago

Cheapest first class flights to Chicago
Explore the most affordable first class flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on July 16, 2026.

This American Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:51 pm
JFK
-
ORD
Nonstop3h 09m
American Airlines
Wed 11/187:22 am
ORD
-
JFK
Nonstop2h 38m
American Airlines
Deal found 7/13$444
This KAYAK deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:20 am
JFK
-
ORD
Nonstop2h 53m
Delta
Thu 7/306:00 am
ORD
-
JFK
Nonstop2h 24m
Delta
Deal found 7/13$468
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:29 am
EWR
-
ORD
Nonstop2h 46m
American Airlines
Wed 8/266:43 am
ORD
-
EWR
Nonstop2h 19m
American Airlines
Deal found 7/11$469
This KAYAK deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:00 am
JFK
-
ORD
1 stop6h 51m
Delta
Wed 8/196:00 am
ORD
-
JFK
Nonstop2h 24m
Delta
Deal found 7/13$473
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:27 am
JFK
-
ORD
Nonstop3h 03m
American Airlines
Wed 9/94:01 pm
ORD
-
JFK
Nonstop2h 28m
American Airlines
Deal found 7/15$481
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:35 pm
JFK
-
ORD
Nonstop3h 08m
Delta
Fri 10/236:10 am
ORD
-
JFK
Nonstop2h 17m
Delta
Deal found 7/11$487

Travel insights for first class flights from New York to Chicago

Get recent, data-driven insights about first class flights from New York to Chicago including ideal travel times, pricing trends, and more.

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

For First Class flights the cheapest month to fly the route is January. The most expensive months are March and June.

Which day of the week is best to fly first class from New York to Chicago?

For the lowest prices, departures on Tuesday are best. Try to avoid leaving on a Monday, as it's usually the most expensive day. For your return flight, Monday is the cheapest day to fly and Sunday is the most expensive.

Frequently Asked Questions about New York to Chicago First Class flights

Find answers to common questions related to First Class tickets for flights to Chicago. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on July 16, 2026.

  • What's cheaper, flying business or first class?

    First class flights are more often than not more expensive than business class. However, average prices on this route are lower for first class at $847 compared to an average of $1,016 for business class tickets.

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