March is by far the best month, wherein you can get cheapest flights for New York to Chicago. Meanwhile, April is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
March- During this month the footfall is less so, the flight is gradually inexpensive.
March - is the cheapest month to book round trip flights.
Cheapest Fare- Currently, this is the fare price based on the current demand.
Disclaimer - All the mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.

New York
16:29
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
18:29
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
13:10
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
17:24
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
16:29
John F Kennedy International Airport [JFK]
Sat , 14 Mar 2026

Chicago
18:29
Chicago O Hare International Airport [ORD]
Sat, 14 Mar 2026

New York
11:59
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
13:56
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
09:25
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
11:25
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
16:29
John F Kennedy International Airport [JFK]
Fri , 13 Mar 2026

Chicago
18:29
Chicago O Hare International Airport [ORD]
Fri, 13 Mar 2026

New York
20:59
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
22:56
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
08:59
John F Kennedy International Airport [JFK]
Thu , 12 Mar 2026

Chicago
10:56
Chicago O Hare International Airport [ORD]
Thu, 12 Mar 2026

New York
08:59
John F Kennedy International Airport [JFK]
Fri , 13 Mar 2026

Chicago
10:56
Chicago O Hare International Airport [ORD]
Fri, 13 Mar 2026

New York
13:55
John F Kennedy International Airport [JFK]
Mon , 16 Mar 2026

Chicago
18:55
Chicago O Hare International Airport [ORD]
Mon, 16 Mar 2026











To crack the better offer on New York to Chicago flights, it’s better to make advanced bookings at least few weeks prior of your intended date because price might rise eventually due to the delay.
Weekdays are the best day to get low-cost flight tickets from New York to Chicago. However, it depends on a certain factor. If the demand is high and festivals are there, then prices could be a little high.