New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 81 with Southwest Airlines.Best fare available on Jul 21, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

19 Jul
Southwest Airlines
21:05LGA
10:20MDW
1 StopUSD 132VIEW DEAL
19 Jul
Southwest Airlines
11:00LGA
13:25MDW
DirectUSD 191VIEW DEAL
19 Jul
Southwest Airlines
07:25LGA
09:50MDW
DirectUSD 209VIEW DEAL
19 Jul
Southwest Airlines
20:55LGA
08:40MDW
1 StopUSD 481VIEW DEAL
20 Jul
Southwest Airlines
06:30LGA
16:35MDW
1 StopUSD 132VIEW DEAL
20 Jul
Frontier Airlines
20:29LGA
12:07MDW
2 StopUSD 222VIEW DEAL
20 Jul
Southwest Airlines
21:30LGA
00:00MDW
DirectUSD 203VIEW DEAL
20 Jul
Southwest Airlines
21:25LGA
07:45MDW
1 StopUSD 253VIEW DEAL
21 Jul
Southwest Airlines
10:55LGA
13:15MDW
DirectUSD 81VIEW DEAL
21 Jul
Southwest Airlines
21:30LGA
00:00MDW
DirectUSD 102VIEW DEAL

New York to Chicago monthly flight fare trend

Jul
from USD 81
Aug
from USD 79
Sep
from USD 68
Oct
from USD 73
Nov
from USD 98
Dec
from USD 76

Airport Details

Origin

New York

LaGuardia Airport (LGA)

New York, LGA
Zone

New York

Elev

21 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from New York

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