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

Saturday, December 26th, 2026

9 round-trip options

Returning
Thu, Dec 31, 2026•5 Day Trip
$499 USD
Google Flights
Returning
Fri, Jan 1, 2027•6 Day Trip
$489 USD
Google Flights
Returning
Sat, Jan 2, 2027•7 Day Trip
$525 USD
Google Flights
Returning
Sun, Jan 3, 2027•8 Day Trip
$592 USD
Google Flights
Returning
Mon, Jan 4, 2027•9 Day Trip
$508 USD
Google Flights
Returning
Tue, Jan 5, 2027•10 Day Trip
$440 USD
Google Flights
Returning
Wed, Jan 6, 2027•11 Day Trip
$420 USD
Google Flights
Returning
Thu, Jan 7, 2027•12 Day Trip
$431 USD
Google Flights
Returning
Fri, Jan 8, 2027•13 Day Trip
$431 USD
Google Flights