Portland (PDX) to Chicago (ORD) flight deal in economy from $315
PDXPortland International Airport
Portland, United States
ORDO'Hare International Airport
Chicago, United States
$367 USD
-14%$315 USD
Verified 1 day agoNovember 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Great Availability
65% of dates checked are available within 10% of the lowest price
Friday, November 27th, 2026
5 round-trip options
Returning
Thu, Dec 3, 2026•6 Day Trip
$405 USD
Returning
Fri, Dec 4, 2026•7 Day Trip
$405 USD
Returning
Sat, Dec 5, 2026•8 Day Trip
$394 USD
Returning
Tue, Dec 8, 2026•11 Day Trip
$394 USD
Returning
Thu, Dec 10, 2026•13 Day Trip
$405 USD