Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at SAR 699 with Southwest Airlines.Best fare available on Sep 5, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Portland cheapest flights this week

20 Aug
Southwest Airlines
20:50MDW
01:05PDX
DirectSAR 892VIEW DEAL
23 Aug
Southwest Airlines
21:20MDW
01:30PDX
DirectSAR 925VIEW DEAL
24 Aug
Southwest Airlines
20:50MDW
01:05PDX
DirectSAR 936VIEW DEAL
25 Aug
Southwest Airlines
20:55MDW
01:10PDX
DirectSAR 844VIEW DEAL
26 Aug
Southwest Airlines
20:55MDW
01:10PDX
DirectSAR 840VIEW DEAL
29 Aug
Southwest Airlines
18:00MDW
22:15PDX
DirectSAR 877VIEW DEAL
2 Sept
Southwest Airlines
20:55MDW
01:10PDX
DirectSAR 888VIEW DEAL
3 Sept
Southwest Airlines
20:50MDW
01:10PDX
DirectSAR 940VIEW DEAL
4 Sept
Southwest Airlines
18:30MDW
22:45PDX
DirectSAR 940VIEW DEAL
5 Sept
Southwest Airlines
18:00MDW
22:15PDX
DirectSAR 699VIEW DEAL

Chicago to Portland monthly flight fare trend

Aug
from SAR 840
Sep
from SAR 503
Oct
from SAR 696
Nov
No flights
Dec
from SAR 4,625
Jan
No flights

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

Portland

Portland International Airport (PDX)

Portland, PDX
Zone

Los Angeles

Elev

31 ft

Flights from Chicago

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