Portland to Chicago
PDXMDW
Fly from Portland to Chicago starting at USD 136 with WN.
Best fare available on May 13, 2026.
Limited seats. Better plans. Book before it's gone.
Portland to Chicago cheapest flights this week
26 Apr
WN
23:55PDX
--:--MDW
Direct$155VIEW DEAL
5 May
WN
05:40PDX
--:--MDW
Direct$238VIEW DEAL
6 May
WN
23:55PDX
--:--MDW
Direct$238VIEW DEAL
13 May
WN
23:55PDX
--:--MDW
Direct$136VIEW DEAL
17 May
WN
05:20PDX
--:--MDW
Direct$166VIEW DEAL
18 May
F9
12:35PDX
--:--MDW
2 Stop$156VIEW DEAL
22 Jul
WN
23:30PDX
--:--MDW
Direct$160VIEW DEAL
23 Jul
WN
23:30PDX
--:--MDW
Direct$174VIEW DEAL
25 Jul
WN
23:30PDX
--:--MDW
Direct$168VIEW DEAL
Portland to Chicago monthly flight fare trend
Apr
from USD 155
May
from USD 136
Jun
No flights
Jul
from USD 160
Aug
No flights
Sep
No flights
Airport Details
Origin
Portland
Portland International Airport (PDX)
Portland, PDX
Zone
Los Angeles
Elev
31 ft
Destination
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
