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

Wednesday, July 22nd, 2026

8 round-trip options

Returning
Mon, Jul 27, 20265 Day Trip
$326 USD
Returning
Tue, Jul 28, 20266 Day Trip
$315 USD
Returning
Wed, Jul 29, 20267 Day Trip
$315 USD
Returning
Thu, Jul 30, 20268 Day Trip
$326 USD
Returning
Fri, Jul 31, 20269 Day Trip
$326 USD
Returning
Sat, Aug 1, 202610 Day Trip
$315 USD
Returning
Sun, Aug 2, 202611 Day Trip
$326 USD
Returning
Wed, Aug 5, 202614 Day Trip
$315 USD