Chicago to New York

MDWLGA

Fly from Chicago to New York starting at USD 96 with Southwest Airlines.Best fare available on May 29, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to New York cheapest flights this week

24 May
Southwest Airlines
08:10MDW
10:15LGA
Direct$103VIEW DEAL
25 May
Southwest Airlines
05:15MDW
07:15LGA
Direct$131VIEW DEAL
26 May
Frontier Airlines
12:27MDW
22:14LGA
1 Stop$149VIEW DEAL
27 May
Southwest Airlines
17:15MDW
19:20LGA
Direct$98VIEW DEAL
29 May
Southwest Airlines
19:50MDW
21:55LGA
Direct$96VIEW DEAL
30 May
Southwest Airlines
18:10MDW
20:15LGA
Direct$102VIEW DEAL
31 May
Southwest Airlines
05:20MDW
07:20LGA
Direct$112VIEW DEAL
1 Jun
Frontier Airlines
06:00MDW
22:14LGA
1 Stop$115VIEW DEAL
2 Jun
Frontier Airlines
12:27MDW
22:14LGA
1 Stop$101VIEW DEAL
4 Jun
Southwest Airlines
05:15MDW
07:15LGA
Direct$104VIEW DEAL

Chicago to New York monthly flight fare trend

May
from USD 73
Jun
from USD 90
Jul
from USD 94
Aug
from USD 88
Sep
from USD 161
Oct
from USD 151

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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