Portland (PDX) to Chicago (ORD) flight deal in economy from $315

American AirlinesAAAmerican Airlines
Round Trip•Economy
United StatesPDX

Portland International Airport

Portland, United States
United StatesORD

O'Hare International Airport

Chicago, United States
$367 USD
-14%$315 USD
Verified 1 day ago
Great Availability
65% of dates checked are available within 10% of the lowest price

Wednesday, December 23rd, 2026

9 round-trip options

Returning
Mon, Dec 28, 2026•5 Day Trip
$495 USD
Google Flights
Returning
Tue, Dec 29, 2026•6 Day Trip
$695 USD
Google Flights
Returning
Wed, Dec 30, 2026•7 Day Trip
$695 USD
Google Flights
Returning
Thu, Dec 31, 2026•8 Day Trip
$456 USD
Google Flights
Returning
Fri, Jan 1, 2027•9 Day Trip
$446 USD
Google Flights
Returning
Sat, Jan 2, 2027•10 Day Trip
$482 USD
Google Flights
Returning
Sun, Jan 3, 2027•11 Day Trip
$549 USD
Google Flights
Returning
Mon, Jan 4, 2027•12 Day Trip
$465 USD
Google Flights
Returning
Tue, Jan 5, 2027•13 Day Trip
$397 USD
Google Flights