New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 70 with Southwest Airlines.Best fare available on Jun 2, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

29 May
Frontier Airlines
06:29LGA
23:02MDW
1 Stop$75VIEW DEAL
30 May
Southwest Airlines
15:35LGA
18:15MDW
Direct$78VIEW DEAL
31 May
Southwest Airlines
06:00LGA
08:25MDW
Direct$120VIEW DEAL
1 Jun
Southwest Airlines
21:45LGA
00:10MDW
Direct$78VIEW DEAL
2 Jun
Southwest Airlines
15:55LGA
18:40MDW
Direct$70VIEW DEAL
7 Jun
Southwest Airlines
06:00LGA
08:20MDW
Direct$112VIEW DEAL
9 Jun
Southwest Airlines
06:00LGA
08:20MDW
Direct$72VIEW DEAL
11 Jun
Southwest Airlines
06:00LGA
08:20MDW
Direct$93VIEW DEAL
15 Jun
Southwest Airlines
21:30LGA
23:55MDW
Direct$114VIEW DEAL
16 Jun
Southwest Airlines
06:00LGA
08:20MDW
Direct$79VIEW DEAL

New York to Chicago monthly flight fare trend

May
from USD 65
Jun
from USD 70
Jul
from USD 91
Aug
from USD 113
Sep
from USD 113
Oct
from USD 206

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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