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

Thursday, December 24th, 2026

9 round-trip options

Returning
Tue, Dec 29, 20265 Day Trip
$595 USD
Returning
Wed, Dec 30, 20266 Day Trip
$595 USD
Returning
Thu, Dec 31, 20267 Day Trip
$405 USD
Returning
Fri, Jan 1, 20278 Day Trip
$395 USD
Returning
Sat, Jan 2, 20279 Day Trip
$431 USD
Returning
Sun, Jan 3, 202710 Day Trip
$498 USD
Returning
Mon, Jan 4, 202711 Day Trip
$414 USD
Returning
Tue, Jan 5, 202712 Day Trip
$346 USD
Returning
Wed, Jan 6, 202713 Day Trip
$326 USD