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Cheap Business Class Flights from New York to Chicago

NYC — CHI
Aug 16 — Aug 231
Sun 8/16
Sun 8/23
1 adult, Business
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Essential info for Business 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 17, 2026.

Top Rated Airline

American Airlines

No. of Airlines

4

Arrival Airport

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

Cheapest business class flights to Chicago
Explore the most affordable business class flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on July 17, 2026.

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 8/185:29 am
EWR
-
ORD
Nonstop2h 46m
American Airlines
Wed 8/198:36 pm
ORD
-
EWR
Nonstop2h 23m
American Airlines
Deal found 7/13$469
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:55 am
EWR
-
ORD
1 stop7h 07m
Frontier
Wed 9/232:03 pm
ORD
-
EWR
1 stop9h 56m
Frontier
Deal found 7/13$515
This Expedia deal was found by Cheapflights users on 7/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:55 am
EWR
-
ORD
1 stop7h 07m
Frontier
Mon 10/52:03 pm
ORD
-
EWR
1 stop6h 25m
Frontier
Deal found 7/16$518
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:25 am
LGA
-
ORD
1 stop6h 37m
Frontier
Thu 9/246:30 am
ORD
-
LGA
1 stop10h 05m
Frontier
Deal found 7/13$522
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:55 am
EWR
-
ORD
1 stop7h 07m
Frontier
Sun 9/274:49 pm
ORD
-
EWR
1 stop16h 38m
Frontier
Deal found 7/13$526
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:29 pm
LGA
-
ORD
1 stop28h 26m
Frontier
Wed 9/232:03 pm
ORD
-
LGA
1 stop8h 12m
Frontier
Deal found 7/13$528

Travel insights for business class flights from New York to Chicago

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

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

For Business Class flights the cheapest month to fly the route is January. The most expensive months are December and July.

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

For the lowest prices, departures on Thursday are best. Try to avoid leaving on a Sunday, 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 Business Class flights

Find answers to common questions related to Business Class tickets for flights to Chicago. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on July 17, 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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