Chicago to New York

MDWJFK

Fly from Chicago to New York starting at USD 219 with Southwest Airlines.Best fare available on Nov 19, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to New York cheapest flights this week

13 Nov
Allegiant Air
15:16MDW
13:15JFK
2 StopUSD 271VIEW DEAL
13 Nov
Frontier Airlines
18:42MDW
12:21JFK
2 StopUSD 347VIEW DEAL
14 Nov
Southwest Airlines
07:40MDW
06:00JFK
1 StopUSD 348VIEW DEAL
15 Nov
Frontier Airlines
18:42MDW
13:16JFK
2 StopUSD 348VIEW DEAL
16 Nov
Frontier Airlines
18:42MDW
13:16JFK
2 StopUSD 320VIEW DEAL
17 Nov
Frontier Airlines
18:42MDW
13:16JFK
2 StopUSD 313VIEW DEAL
18 Nov
Frontier Airlines
06:08MDW
16:29JFK
2 StopUSD 330VIEW DEAL
19 Nov
Southwest Airlines
11:40MDW
09:35JFK
1 StopUSD 219VIEW DEAL
19 Nov
Frontier Airlines
06:08MDW
22:58JFK
2 StopUSD 367VIEW DEAL
20 Nov
Frontier Airlines
13:06MDW
22:58JFK
2 StopUSD 453VIEW DEAL

Chicago to New York monthly flight fare trend

Nov
from USD 219
Dec
from USD 163
Jan
from USD 324
Feb
from USD 182
Mar
from USD 224
Apr
from USD 401

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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