New York to Chicago

JFKMDW

Fly from New York to Chicago starting at USD 166 with Frontier Airlines.Best fare available on Sep 11, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

11 Sept
Frontier Airlines
13:00JFK
18:51MDW
1 StopUSD 166VIEW DEAL
11 Sept
JetBlue Airways
15:45JFK
18:51MDW
2 StopUSD 287VIEW DEAL
12 Sept
Frontier Airlines
13:00JFK
18:51MDW
1 StopUSD 269VIEW DEAL
12 Sept
JetBlue Airways
06:45JFK
18:51MDW
2 StopUSD 169VIEW DEAL
13 Sept
Frontier Airlines
13:00JFK
18:46MDW
1 StopUSD 353VIEW DEAL
13 Sept
JetBlue Airways
06:45JFK
18:51MDW
3 StopUSD 255VIEW DEAL
13 Sept
JetBlue Airways
20:45JFK
12:59MDW
2 StopUSD 366VIEW DEAL
14 Sept
Frontier Airlines
13:00JFK
18:51MDW
1 StopUSD 360VIEW DEAL
14 Sept
JetBlue Airways
20:30JFK
18:51MDW
2 StopUSD 224VIEW DEAL
14 Sept
JetBlue Airways
19:20JFK
18:46MDW
2 StopUSD 245VIEW DEAL

New York to Chicago monthly flight fare trend

Sep
from USD 111
Oct
from USD 127
Nov
from USD 224
Dec
from USD 224
Jan
from USD 353
Feb
from USD 383

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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