Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at SAR 611 with Southwest Airlines.Best fare available on Dec 15, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Portland cheapest flights this week

29 Sept
Frontier Airlines
06:25MDW
13:36PDX
3 StopSAR 999VIEW DEAL
30 Sept
Southwest Airlines
20:55MDW
01:15PDX
DirectSAR 1,114VIEW DEAL
1 Oct
Southwest Airlines
21:45MDW
02:10PDX
DirectSAR 944VIEW DEAL
4 Oct
Southwest Airlines
22:30MDW
03:00PDX
DirectSAR 958VIEW DEAL
7 Oct
Southwest Airlines
10:05MDW
14:30PDX
DirectSAR 696VIEW DEAL
8 Oct
Southwest Airlines
21:45MDW
02:15PDX
DirectSAR 1,055VIEW DEAL
12 Oct
Southwest Airlines
21:45MDW
02:15PDX
DirectSAR 629VIEW DEAL
15 Dec
Southwest Airlines
10:00MDW
14:35PDX
DirectSAR 611VIEW DEAL
15 Dec
Southwest Airlines
20:40MDW
01:20PDX
DirectSAR 625VIEW DEAL
25 Dec
AeroMéxico
06:00MDW
22:57PDX
2 StopSAR 4,625VIEW DEAL

Chicago to Portland monthly flight fare trend

Sep
from SAR 999
Oct
from SAR 629
Nov
No flights
Dec
from SAR 611
Jan
No flights
Feb
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

Flights from Chicago to AtlantaFlights from Chicago to AustinFlights from Chicago to BostonFlights from Chicago to CharlotteFlights from Chicago to DenverFlights from Chicago to DallasFlights from Chicago to DetroitFlights from Chicago to NewarkFlights from Chicago to Fort LauderdaleFlights from Chicago to Honolulu