Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at USD 158 with Southwest Airlines.Best fare available on Sep 5, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

1 Aug
Southwest Airlines
23:30PDX
03:20MDW
DirectUSD 250VIEW DEAL
5 Aug
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 235VIEW DEAL
9 Aug
Southwest Airlines
21:25PDX
03:45MDW
1 StopUSD 261VIEW DEAL
14 Aug
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 258VIEW DEAL
20 Aug
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 259VIEW DEAL
20 Aug
Southwest Airlines
11:35PDX
15:35MDW
DirectUSD 192VIEW DEAL
20 Aug
Southwest Airlines
06:15PDX
10:10MDW
DirectUSD 169VIEW DEAL
5 Sept
Southwest Airlines
07:35PDX
11:35MDW
DirectUSD 184VIEW DEAL
5 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 158VIEW DEAL
11 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 191VIEW DEAL

Portland to Chicago monthly flight fare trend

Aug
from USD 169
Sep
from USD 158
Oct
No flights
Nov
No flights
Dec
No flights
Jan
No flights

Airport Details

Origin

Portland

Portland International Airport (PDX)

Portland, PDX
Zone

Los Angeles

Elev

31 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from Portland

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