Chicago to New York

MDWLGA

Fly from Chicago to New York starting at USD 88 with Southwest Airlines.Best fare available on Jul 29, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to New York cheapest flights this week

26 Jul
Southwest Airlines
05:20MDW
07:20LGA
DirectUSD 214VIEW DEAL
26 Jul
Southwest Airlines
06:30MDW
14:00LGA
1 StopUSD 238VIEW DEAL
27 Jul
Southwest Airlines
05:15MDW
07:15LGA
DirectUSD 207VIEW DEAL
27 Jul
Southwest Airlines
18:00MDW
22:25LGA
1 StopUSD 186VIEW DEAL
28 Jul
Southwest Airlines
05:15MDW
07:15LGA
DirectUSD 172VIEW DEAL
29 Jul
Southwest Airlines
05:15MDW
07:15LGA
DirectUSD 88VIEW DEAL
29 Jul
Southwest Airlines
19:45MDW
22:00LGA
DirectUSD 91VIEW DEAL
29 Jul
Southwest Airlines
13:10MDW
15:15LGA
DirectUSD 127VIEW DEAL
30 Jul
Southwest Airlines
05:15MDW
07:15LGA
DirectUSD 127VIEW DEAL
30 Jul
Southwest Airlines
19:45MDW
22:00LGA
DirectUSD 204VIEW DEAL

Chicago to New York monthly flight fare trend

Jul
from USD 88
Aug
from USD 66
Sep
from USD 65
Oct
from USD 71
Nov
from USD 76
Dec
from USD 135

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

New York

LaGuardia Airport (LGA)

New York, LGA
Zone

New York

Elev

21 ft

Flights from Chicago

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