New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 83 with Southwest Airlines.Best fare available on Oct 1, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

30 Sept
Frontier Airlines
06:15LGA
18:51MDW
1 StopUSD 128VIEW DEAL
30 Sept
Southwest Airlines
10:55LGA
13:15MDW
DirectUSD 127VIEW DEAL
30 Sept
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 127VIEW DEAL
30 Sept
Southwest Airlines
07:25LGA
09:45MDW
DirectUSD 149VIEW DEAL
30 Sept
Southwest Airlines
21:35LGA
23:55MDW
DirectUSD 136VIEW DEAL
1 Oct
Southwest Airlines
07:15LGA
09:35MDW
DirectUSD 110VIEW DEAL
1 Oct
Southwest Airlines
10:55LGA
13:15MDW
DirectUSD 83VIEW DEAL
1 Oct
Frontier Airlines
16:55LGA
00:44MDW
1 StopUSD 166VIEW DEAL
1 Oct
Southwest Airlines
08:55LGA
11:25MDW
DirectUSD 136VIEW DEAL
1 Oct
Frontier Airlines
06:15LGA
18:46MDW
1 StopUSD 160VIEW DEAL

New York to Chicago monthly flight fare trend

Sep
from USD 127
Oct
from USD 73
Nov
from USD 86
Dec
from USD 76
Jan
from USD 133
Feb
from USD 134

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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