New York to Chicago

JFKMDW

Fly from New York to Chicago starting at USD 161 with Frontier Airlines.Best fare available on Aug 13, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

12 Aug
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 256VIEW DEAL
12 Aug
JetBlue Airways
21:45JFK
23:03MDW
2 StopUSD 607VIEW DEAL
13 Aug
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 161VIEW DEAL
13 Aug
JetBlue Airways
06:29JFK
15:10MDW
1 StopUSD 322VIEW DEAL
14 Aug
Frontier Airlines
13:00JFK
10:51MDW
1 StopUSD 297VIEW DEAL
15 Aug
Frontier Airlines
13:00JFK
23:03MDW
1 StopUSD 323VIEW DEAL
16 Aug
JetBlue Airways
06:50JFK
23:03MDW
1 StopUSD 207VIEW DEAL
16 Aug
JetBlue Airways
21:00JFK
10:51MDW
1 StopUSD 324VIEW DEAL
16 Aug
Frontier Airlines
13:00JFK
10:51MDW
1 StopUSD 381VIEW DEAL
17 Aug
JetBlue Airways
12:00JFK
23:03MDW
1 StopUSD 232VIEW DEAL

New York to Chicago monthly flight fare trend

Aug
from USD 150
Sep
from USD 82
Oct
from USD 97
Nov
from USD 237
Dec
from USD 285
Jan
from USD 410

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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