Chicago to New York

MDWJFK

Fly from Chicago to New York starting at USD 182 with Southwest Airlines.Best fare available on Aug 10, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to New York cheapest flights this week

9 Aug
Southwest Airlines
06:00MDW
19:35JFK
1 StopUSD 327VIEW DEAL
9 Aug
Frontier Airlines
06:05MDW
10:50JFK
1 StopUSD 333VIEW DEAL
9 Aug
Volaris
20:23MDW
23:20JFK
2 StopUSD 509VIEW DEAL
10 Aug
Frontier Airlines
11:06MDW
10:50JFK
1 StopUSD 353VIEW DEAL
10 Aug
Southwest Airlines
18:30MDW
07:02JFK
1 StopUSD 182VIEW DEAL
10 Aug
Frontier Airlines
06:05MDW
10:50JFK
1 StopUSD 276VIEW DEAL
11 Aug
Frontier Airlines
11:06MDW
10:50JFK
1 StopUSD 312VIEW DEAL
11 Aug
Frontier Airlines
06:05MDW
10:50JFK
1 StopUSD 300VIEW DEAL
12 Aug
Frontier Airlines
06:05MDW
10:50JFK
1 StopUSD 271VIEW DEAL
12 Aug
Frontier Airlines
11:06MDW
10:50JFK
1 StopUSD 338VIEW DEAL

Chicago to New York monthly flight fare trend

Aug
from USD 182
Sep
from USD 177
Oct
from USD 141
Nov
from USD 217
Dec
from USD 284
Jan
from USD 541

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

New York

John F Kennedy International Airport (JFK)

New York, JFK
Zone

New York

Elev

13 ft

Flights from Chicago

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