Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at USD 189 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
DirectUSD 241VIEW DEAL
23 Aug
Southwest Airlines
21:20MDW
01:30PDX
DirectUSD 250VIEW DEAL
24 Aug
Southwest Airlines
20:50MDW
01:05PDX
DirectUSD 253VIEW DEAL
25 Aug
Southwest Airlines
20:55MDW
01:10PDX
DirectUSD 228VIEW DEAL
26 Aug
Southwest Airlines
20:55MDW
01:10PDX
DirectUSD 227VIEW DEAL
29 Aug
Southwest Airlines
18:00MDW
22:15PDX
DirectUSD 237VIEW DEAL
2 Sept
Southwest Airlines
20:55MDW
01:10PDX
DirectUSD 240VIEW DEAL
3 Sept
Southwest Airlines
20:50MDW
01:10PDX
DirectUSD 254VIEW DEAL
4 Sept
Southwest Airlines
18:30MDW
22:45PDX
DirectUSD 254VIEW DEAL
5 Sept
Southwest Airlines
18:00MDW
22:15PDX
DirectUSD 189VIEW DEAL

Chicago to Portland monthly flight fare trend

Aug
from USD 227
Sep
from USD 136
Oct
from USD 188
Nov
No flights
Dec
from USD 1,250
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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