Portland to Chicago

PDXMDW

Fly from Portland to Chicago starting at USD 174 with Southwest Airlines.Best fare available on Sep 16, 2026.Limited seats. Better plans. Book before it's gone.

Portland to Chicago cheapest flights this week

9 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 224VIEW DEAL
11 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 191VIEW DEAL
11 Sept
Southwest Airlines
11:35PDX
15:35MDW
DirectUSD 208VIEW DEAL
12 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 227VIEW DEAL
13 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 209VIEW DEAL
15 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 225VIEW DEAL
16 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 209VIEW DEAL
16 Sept
Southwest Airlines
07:50PDX
14:35MDW
1 StopUSD 174VIEW DEAL
17 Sept
Southwest Airlines
23:30PDX
03:25MDW
DirectUSD 209VIEW DEAL
25 Sept
Southwest Airlines
11:35PDX
15:35MDW
DirectUSD 216VIEW DEAL

Portland to Chicago monthly flight fare trend

Sep
from USD 174
Oct
from USD 174
Nov
No flights
Dec
from USD 175
Jan
No flights
Feb
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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