Portland to Chicago
PDXMDW
Fly from Portland to Chicago starting at SAR 510 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
10:50MDW
DirectSAR 581VIEW DEAL
5 May
WN
05:40PDX
16:35MDW
DirectSAR 893VIEW DEAL
6 May
WN
23:55PDX
10:50MDW
DirectSAR 893VIEW DEAL
13 May
WN
23:55PDX
10:50MDW
DirectSAR 510VIEW DEAL
17 May
WN
05:20PDX
16:15MDW
DirectSAR 623VIEW DEAL
18 May
F9
12:35PDX
16:09MDW
2 StopSAR 585VIEW DEAL
22 Jul
WN
23:30PDX
10:20MDW
DirectSAR 600VIEW DEAL
23 Jul
WN
23:30PDX
10:20MDW
DirectSAR 653VIEW DEAL
25 Jul
WN
23:30PDX
10:20MDW
DirectSAR 630VIEW DEAL
Portland to Chicago monthly flight fare trend
Apr
from SAR 581
May
from SAR 510
Jun
No flights
Jul
from SAR 600
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
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