New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 97 with Southwest Airlines.Best fare available on Aug 13, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

13 Aug
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 102VIEW DEAL
13 Aug
Southwest Airlines
16:25LGA
22:30MDW
1 StopUSD 97VIEW DEAL
13 Aug
Southwest Airlines
15:00LGA
20:45MDW
1 StopUSD 154VIEW DEAL
13 Aug
Southwest Airlines
21:40LGA
07:30MDW
1 StopUSD 206VIEW DEAL
14 Aug
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 107VIEW DEAL
14 Aug
Southwest Airlines
15:00LGA
20:45MDW
1 StopUSD 241VIEW DEAL
15 Aug
Southwest Airlines
17:50LGA
20:15MDW
DirectUSD 113VIEW DEAL
15 Aug
Southwest Airlines
07:35LGA
09:55MDW
DirectUSD 237VIEW DEAL
15 Aug
Southwest Airlines
07:00LGA
20:10MDW
1 StopUSD 143VIEW DEAL
15 Aug
Southwest Airlines
15:20LGA
17:50MDW
DirectUSD 218VIEW DEAL

New York to Chicago monthly flight fare trend

Aug
from USD 79
Sep
from USD 70
Oct
from USD 73
Nov
from USD 84
Dec
from USD 76
Jan
from USD 163

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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