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

Thursday, December 24th, 2026

9 round-trip options

Returning
Tue, Dec 29, 2026•5 Day Trip
$595 USD
Google Flights
Returning
Wed, Dec 30, 2026•6 Day Trip
$595 USD
Google Flights
Returning
Thu, Dec 31, 2026•7 Day Trip
$405 USD
Google Flights
Returning
Fri, Jan 1, 2027•8 Day Trip
$395 USD
Google Flights
Returning
Sat, Jan 2, 2027•9 Day Trip
$431 USD
Google Flights
Returning
Sun, Jan 3, 2027•10 Day Trip
$498 USD
Google Flights
Returning
Mon, Jan 4, 2027•11 Day Trip
$414 USD
Google Flights
Returning
Tue, Jan 5, 2027•12 Day Trip
$346 USD
Google Flights
Returning
Wed, Jan 6, 2027•13 Day Trip
$326 USD
Google Flights