New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 72 with Southwest Airlines.Best fare available on Jun 9, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

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
17 Jun
Southwest Airlines
06:00LGA
08:20MDW
Direct$92VIEW DEAL
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

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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