New York to Chicago

JFKMDW

Fly from New York to Chicago starting at USD 174 with JetBlue Airways.Best fare available on Sep 6, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

3 Sept
Frontier Airlines
13:00JFK
11:55MDW
1 StopUSD 481VIEW DEAL
3 Sept
JetBlue Airways
20:59JFK
23:47MDW
1 StopUSD 487VIEW DEAL
3 Sept
JetBlue Airways
21:30JFK
11:50MDW
2 StopUSD 557VIEW DEAL
4 Sept
Frontier Airlines
13:00JFK
23:47MDW
1 StopUSD 208VIEW DEAL
4 Sept
JetBlue Airways
21:30JFK
23:47MDW
2 StopUSD 326VIEW DEAL
4 Sept
JetBlue Airways
16:50JFK
23:47MDW
2 StopUSD 302VIEW DEAL
5 Sept
Frontier Airlines
13:00JFK
23:47MDW
1 StopUSD 202VIEW DEAL
6 Sept
Frontier Airlines
13:00JFK
23:47MDW
1 StopUSD 253VIEW DEAL
6 Sept
JetBlue Airways
20:59JFK
11:55MDW
1 StopUSD 174VIEW DEAL
7 Sept
Frontier Airlines
13:00JFK
11:55MDW
1 StopUSD 357VIEW DEAL

New York to Chicago monthly flight fare trend

Sep
from USD 108
Oct
from USD 129
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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