Portland (PDX) to Chicago (ORD) flight deal in economy from $315
PDXPortland International Airport
Portland, United States
ORDO'Hare International Airport
Chicago, United States
$367 USD
-14%$315 USD
Verified 1 day agoOctober 2026
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Great Availability
65% of dates checked are available within 10% of the lowest price
Friday, October 23rd, 2026
5 round-trip options
Returning
Thu, Oct 29, 2026•6 Day Trip
$363 USD
Returning
Fri, Oct 30, 2026•7 Day Trip
$363 USD
Returning
Sat, Oct 31, 2026•8 Day Trip
$352 USD
Returning
Tue, Nov 3, 2026•11 Day Trip
$352 USD
Returning
Thu, Nov 5, 2026•13 Day Trip
$373 USD