New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 104 with Southwest Airlines.Best fare available on Aug 4, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

1 Aug
Southwest Airlines
17:35LGA
20:25MDW
DirectUSD 170VIEW DEAL
1 Aug
Southwest Airlines
06:00LGA
08:20MDW
DirectUSD 129VIEW DEAL
1 Aug
Southwest Airlines
21:10LGA
23:50MDW
DirectUSD 167VIEW DEAL
1 Aug
Southwest Airlines
08:15LGA
18:05MDW
1 StopUSD 225VIEW DEAL
2 Aug
Southwest Airlines
06:00LGA
08:20MDW
DirectUSD 145VIEW DEAL
2 Aug
Southwest Airlines
07:25LGA
09:50MDW
DirectUSD 211VIEW DEAL
3 Aug
Southwest Airlines
21:30LGA
00:00MDW
DirectUSD 107VIEW DEAL
3 Aug
Southwest Airlines
07:25LGA
09:50MDW
DirectUSD 118VIEW DEAL
4 Aug
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 104VIEW DEAL
4 Aug
Southwest Airlines
08:50LGA
16:25MDW
1 StopUSD 202VIEW DEAL

New York to Chicago monthly flight fare trend

Aug
from USD 79
Sep
from USD 69
Oct
from USD 73
Nov
from USD 98
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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