Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at USD 124 with Southwest Airlines.Best fare available on Aug 20, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

17 Jul
Southwest Airlines
23:30PDX
03:20MDW
DirectUSD 241VIEW DEAL
22 Jul
Southwest Airlines
23:30PDX
03:20MDW
DirectUSD 160VIEW DEAL
23 Jul
Southwest Airlines
23:30PDX
03:20MDW
DirectUSD 174VIEW DEAL
25 Jul
Southwest Airlines
23:30PDX
03:20MDW
DirectUSD 168VIEW DEAL
20 Aug
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 124VIEW DEAL
25 Sept
Southwest Airlines
11:35PDX
15:35MDW
DirectUSD 216VIEW DEAL

Portland to Chicago monthly flight fare trend

Jul
from USD 160
Aug
from USD 124
Sep
from USD 216
Oct
No flights
Nov
No flights
Dec
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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