Portland to Chicago
PDXMDW
Fly from Portland to Chicago starting at USD 160 with Southwest Airlines.
Best fare available on Jul 22, 2026.
Limited seats. Better plans. Book before it's gone.
Portland to Chicago cheapest flights this week
Portland to Chicago monthly flight fare trend
May
from USD 136
Jun
No flights
Jul
from USD 160
Aug
No flights
Sep
No flights
Oct
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
Flights from Portland to AtlantaFlights from Portland to AustinFlights from Portland to BostonFlights from Portland to CharlotteFlights from Portland to DenverFlights from Portland to DallasFlights from Portland to DetroitFlights from Portland to NewarkFlights from Portland to Fort LauderdaleFlights from Portland to Honolulu
