Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at USD 162 with Southwest Airlines.Best fare available on Aug 18, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Portland cheapest flights this week

31 Jul
Southwest Airlines
16:40MDW
21:00PDX
DirectUSD 197VIEW DEAL
1 Aug
Southwest Airlines
10:25MDW
01:30PDX
1 StopUSD 269VIEW DEAL
1 Aug
Southwest Airlines
07:50MDW
18:50PDX
1 StopUSD 226VIEW DEAL
3 Aug
Southwest Airlines
21:35MDW
01:55PDX
DirectUSD 257VIEW DEAL
4 Aug
Southwest Airlines
20:55MDW
01:10PDX
DirectUSD 230VIEW DEAL
9 Aug
Southwest Airlines
05:25MDW
13:05PDX
1 StopUSD 258VIEW DEAL
18 Aug
Southwest Airlines
18:00MDW
00:15PDX
1 StopUSD 162VIEW DEAL
5 Sept
Southwest Airlines
18:00MDW
22:15PDX
DirectUSD 189VIEW DEAL
9 Sept
Southwest Airlines
20:55MDW
01:15PDX
DirectUSD 185VIEW DEAL
29 Sept
Frontier Airlines
06:25MDW
13:36PDX
3 StopUSD 270VIEW DEAL

Chicago to Portland monthly flight fare trend

Jul
from USD 197
Aug
from USD 162
Sep
from USD 185
Oct
from USD 188
Nov
No flights
Dec
from USD 1,250

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

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