New York to Chicago

LGAMDW

Fly from New York to Chicago starting at USD 71 with Southwest Airlines.Best fare available on Sep 9, 2026.Limited seats. Better plans. Book before it's gone.

New York to Chicago cheapest flights this week

6 Sept
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 143VIEW DEAL
6 Sept
Southwest Airlines
21:35LGA
23:50MDW
DirectUSD 188VIEW DEAL
6 Sept
Southwest Airlines
08:30LGA
10:55MDW
DirectUSD 152VIEW DEAL
6 Sept
Frontier Airlines
06:18LGA
11:55MDW
1 StopUSD 146VIEW DEAL
6 Sept
Southwest Airlines
18:45LGA
23:45MDW
1 StopUSD 161VIEW DEAL
7 Sept
Southwest Airlines
20:55LGA
23:15MDW
DirectUSD 142VIEW DEAL
7 Sept
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 177VIEW DEAL
8 Sept
Southwest Airlines
21:35LGA
23:55MDW
DirectUSD 146VIEW DEAL
8 Sept
Southwest Airlines
06:00LGA
08:15MDW
DirectUSD 147VIEW DEAL
9 Sept
Southwest Airlines
16:10LGA
18:40MDW
DirectUSD 71VIEW DEAL

New York to Chicago monthly flight fare trend

Sep
from USD 70
Oct
from USD 73
Nov
from USD 86
Dec
from USD 76
Jan
from USD 127
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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