Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at SAR 681 with Southwest Airlines.Best fare available on Oct 3, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

20 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 921VIEW DEAL
21 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 829VIEW DEAL
23 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 895VIEW DEAL
24 Sept
Southwest Airlines
06:15PDX
10:10MDW
DirectSAR 947VIEW DEAL
25 Sept
Southwest Airlines
11:35PDX
15:35MDW
DirectSAR 951VIEW DEAL
25 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 944VIEW DEAL
27 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 944VIEW DEAL
28 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectSAR 969VIEW DEAL
3 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectSAR 681VIEW DEAL
6 Oct
Southwest Airlines
23:35PDX
03:25MDW
DirectSAR 681VIEW DEAL

Portland to Chicago monthly flight fare trend

Sep
from SAR 829
Oct
from SAR 644
Nov
No flights
Dec
from SAR 648
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

Flights from Portland

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