New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 91 with Southwest Airlines.Best fare available on Jul 24, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

26 Jun
Southwest Airlines
21:30LGA
23:55MDW
Direct$115VIEW DEAL
1 Jul
Southwest Airlines
06:00LGA
08:20MDW
Direct$93VIEW DEAL
19 Jul
Southwest Airlines
21:05LGA
10:20MDW
1 Stop$132VIEW DEAL
20 Jul
Southwest Airlines
06:30LGA
16:35MDW
1 Stop$132VIEW DEAL
24 Jul
Southwest Airlines
21:30LGA
23:55MDW
Direct$91VIEW DEAL
28 Jul
Southwest Airlines
07:25LGA
09:50MDW
Direct$92VIEW DEAL
15 Aug
Southwest Airlines
17:50LGA
20:15MDW
Direct$113VIEW DEAL
24 Aug
Southwest Airlines
06:00LGA
08:15MDW
Direct$120VIEW DEAL
10 Sept
Southwest Airlines
06:00LGA
08:15MDW
Direct$113VIEW DEAL
21 Sept
Southwest Airlines
06:00LGA
08:15MDW
Direct$252VIEW DEAL

New York to Chicago monthly flight fare trend

Jun
from USD 70
Jul
from USD 91
Aug
from USD 113
Sep
from USD 113
Oct
from USD 206
Nov
from USD 528

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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