Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at USD 174 with Southwest Airlines.Best fare available on Oct 14, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

28 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 288VIEW DEAL
29 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 266VIEW DEAL
1 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectUSD 256VIEW DEAL
3 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectUSD 184VIEW DEAL
6 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectUSD 184VIEW DEAL
7 Oct
Southwest Airlines
14:25PDX
21:50MDW
1 StopUSD 269VIEW DEAL
9 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectUSD 261VIEW DEAL
14 Oct
Southwest Airlines
20:45PDX
03:45MDW
1 StopUSD 203VIEW DEAL
14 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectUSD 174VIEW DEAL
15 Dec
Southwest Airlines
06:00PDX
09:50MDW
DirectUSD 175VIEW DEAL

Portland to Chicago monthly flight fare trend

Sep
from USD 266
Oct
from USD 174
Nov
No flights
Dec
from USD 175
Jan
No flights
Feb
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

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