New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 93 with Southwest Airlines.Best fare available on Jul 1, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

1 Jul
Southwest Airlines
06:00LGA
08:20MDW
DirectUSD 93VIEW DEAL
2 Jul
Southwest Airlines
06:00LGA
08:20MDW
DirectUSD 202VIEW DEAL
3 Jul
Southwest Airlines
15:25LGA
18:05MDW
DirectUSD 208VIEW DEAL
4 Jul
Southwest Airlines
16:35LGA
19:25MDW
DirectUSD 121VIEW DEAL
5 Jul
Southwest Airlines
07:25LGA
09:50MDW
DirectUSD 218VIEW DEAL
6 Jul
Southwest Airlines
17:30LGA
20:20MDW
DirectUSD 226VIEW DEAL
7 Jul
Southwest Airlines
10:55LGA
13:15MDW
DirectUSD 151VIEW DEAL
8 Jul
Southwest Airlines
10:55LGA
13:15MDW
DirectUSD 157VIEW DEAL
9 Jul
Southwest Airlines
06:00LGA
08:20MDW
DirectUSD 190VIEW DEAL
10 Jul
Southwest Airlines
17:30LGA
20:20MDW
DirectUSD 194VIEW DEAL

New York to Chicago monthly flight fare trend

Jul
from USD 81
Aug
from USD 88
Sep
from USD 86
Oct
from USD 88
Nov
from USD 528
Dec
from USD 135

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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