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 agoOctober 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Great Availability
65% of dates checked are available within 10% of the lowest price
Monday, October 19th, 2026
5 round-trip options
Returning
Sun, Oct 25, 2026•6 Day Trip
$337 USD
Returning
Mon, Oct 26, 2026•7 Day Trip
$337 USD
Returning
Tue, Oct 27, 2026•8 Day Trip
$326 USD
Returning
Fri, Oct 30, 2026•11 Day Trip
$337 USD
Returning
Sun, Nov 1, 2026•13 Day Trip
$337 USD