Chicago to Portland

MDWPDX

Fly from Chicago to Portland starting at USD 136 with Southwest Airlines.Best fare available on Sep 10, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Portland cheapest flights this week

3 Sept
Southwest Airlines
20:50MDW
01:10PDX
DirectUSD 254VIEW DEAL
3 Sept
Southwest Airlines
19:35MDW
01:45PDX
1 StopUSD 282VIEW DEAL
4 Sept
Southwest Airlines
18:30MDW
22:45PDX
DirectUSD 263VIEW DEAL
5 Sept
Southwest Airlines
18:00MDW
22:15PDX
DirectUSD 189VIEW DEAL
9 Sept
Southwest Airlines
20:55MDW
01:15PDX
DirectUSD 201VIEW DEAL
10 Sept
Southwest Airlines
18:30MDW
22:45PDX
DirectUSD 136VIEW DEAL
10 Sept
Southwest Airlines
20:50MDW
01:10PDX
DirectUSD 203VIEW DEAL
11 Sept
Southwest Airlines
18:30MDW
22:45PDX
DirectUSD 203VIEW DEAL
11 Sept
Southwest Airlines
20:50MDW
01:10PDX
DirectUSD 202VIEW DEAL
13 Sept
Southwest Airlines
21:20MDW
01:35PDX
DirectUSD 257VIEW DEAL

Chicago to Portland monthly flight fare trend

Sep
from USD 136
Oct
from USD 170
Nov
No flights
Dec
from USD 165
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

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