New York to Chicago

JFKMDW

Fly from New York to Chicago starting at USD 221 with JetBlue Airways.Best fare available on Aug 4, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

1 Aug
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 300VIEW DEAL
1 Aug
JetBlue Airways
17:00JFK
12:07MDW
2 StopUSD 359VIEW DEAL
1 Aug
JetBlue Airways
21:30JFK
23:03MDW
2 StopUSD 483VIEW DEAL
2 Aug
JetBlue Airways
22:52JFK
12:07MDW
2 StopUSD 334VIEW DEAL
2 Aug
JetBlue Airways
22:29JFK
08:00MDW
1 StopUSD 349VIEW DEAL
2 Aug
JetBlue Airways
21:30JFK
12:07MDW
2 StopUSD 298VIEW DEAL
3 Aug
Frontier Airlines
13:00JFK
12:07MDW
1 StopUSD 300VIEW DEAL
4 Aug
Frontier Airlines
13:00JFK
10:51MDW
1 StopUSD 374VIEW DEAL
4 Aug
JetBlue Airways
20:59JFK
10:51MDW
1 StopUSD 221VIEW DEAL
5 Aug
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 315VIEW DEAL

New York to Chicago monthly flight fare trend

Aug
from USD 127
Sep
from USD 123
Oct
from USD 124
Nov
from USD 238
Dec
from USD 407
Jan
from USD 525

Airport Details

Origin

New York

John F Kennedy International Airport (JFK)

New York, JFK
Zone

New York

Elev

13 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from New York

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