Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at USD 165 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

8 Oct
Southwest Airlines
21:45MDW
02:15PDX
DirectUSD 285VIEW DEAL
11 Oct
Southwest Airlines
22:30MDW
03:00PDX
DirectUSD 285VIEW DEAL
12 Oct
Southwest Airlines
21:45MDW
02:15PDX
DirectUSD 170VIEW DEAL
15 Dec
Southwest Airlines
10:00MDW
14:35PDX
DirectUSD 165VIEW DEAL
15 Dec
Southwest Airlines
20:40MDW
01:20PDX
DirectUSD 169VIEW DEAL
21 Dec
Southwest Airlines
21:25MDW
02:05PDX
DirectUSD 200VIEW DEAL
25 Dec
AeroMéxico
06:00MDW
22:57PDX
2 StopUSD 1,250VIEW DEAL

Chicago to Portland monthly flight fare trend

Oct
from USD 170
Nov
No flights
Dec
from USD 165
Jan
No flights
Feb
No flights
Mar
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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