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 agoDecember 2026
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Great Availability
65% of dates checked are available within 10% of the lowest price
Sunday, December 20th, 2026
9 round-trip options
Returning
Fri, Dec 25, 2026•5 Day Trip
$337 USD
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Sat, Dec 26, 2026•6 Day Trip
$519 USD
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Sun, Dec 27, 2026•7 Day Trip
$679 USD
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Mon, Dec 28, 2026•8 Day Trip
$444 USD
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Tue, Dec 29, 2026•9 Day Trip
$595 USD
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Wed, Dec 30, 2026•10 Day Trip
$595 USD
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Thu, Dec 31, 2026•11 Day Trip
$405 USD
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Fri, Jan 1, 2027•12 Day Trip
$395 USD
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Sat, Jan 2, 2027•13 Day Trip
$431 USD