Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at USD 175 with Southwest Airlines.Best fare available on Dec 15, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

13 Nov
Southwest Airlines
23:30PDX
03:15MDW
DirectUSD 231VIEW DEAL
14 Nov
Southwest Airlines
05:55PDX
12:45MDW
1 StopUSD 309VIEW DEAL
20 Nov
Southwest Airlines
23:30PDX
03:15MDW
DirectUSD 299VIEW DEAL
15 Dec
Southwest Airlines
06:00PDX
09:50MDW
DirectUSD 175VIEW DEAL
20 Dec
Southwest Airlines
23:30PDX
03:15MDW
DirectUSD 329VIEW DEAL
21 Dec
Southwest Airlines
20:15PDX
03:00MDW
1 StopUSD 208VIEW DEAL

Portland to Chicago monthly flight fare trend

Nov
from USD 231
Dec
from USD 175
Jan
from USD 201
Feb
No flights
Mar
No flights
Apr
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

Flights from Portland

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