New York to Chicago

JFKMDW

Fly from New York to Chicago starting at USD 223 with JetBlue Airways.Best fare available on Jul 20, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

19 Jul
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 321VIEW DEAL
19 Jul
JetBlue Airways
22:29JFK
08:00MDW
1 StopUSD 309VIEW DEAL
19 Jul
JetBlue Airways
22:35JFK
17:51MDW
3 StopUSD 828VIEW DEAL
20 Jul
Frontier Airlines
13:00JFK
12:07MDW
1 StopUSD 295VIEW DEAL
20 Jul
JetBlue Airways
22:29JFK
08:10MDW
1 StopUSD 223VIEW DEAL
20 Jul
JetBlue Airways
22:52JFK
23:03MDW
2 StopUSD 548VIEW DEAL
21 Jul
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 348VIEW DEAL
21 Jul
JetBlue Airways
06:50JFK
23:03MDW
1 StopUSD 396VIEW DEAL
21 Jul
JetBlue Airways
22:29JFK
08:10MDW
1 StopUSD 310VIEW DEAL
22 Jul
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 290VIEW DEAL

New York to Chicago monthly flight fare trend

Jul
from USD 163
Aug
from USD 134
Sep
from USD 135
Oct
from USD 140
Nov
from USD 238
Dec
from USD 407

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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