$126 Cheap American Airlines flights Portland (PDX) to Chicago (ORD)

View $126 flight on Sat, Apr 25, 2026Opens in a new window

$126 Cheap American Airlines flights Portland (PDX) to Chicago (ORD)

Prices were available within the past 7 days and start at $126 for one-way flights and $278 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Apr 25 - Tue, Apr 28
PDX
Portland
ORD
Chicago
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 25 from Portland to Chicago, returning Tue, Apr 28, priced at $278 found 5 days ago
American Airlines
Sat, Apr 25 - Tue, Apr 28
PDX
Portland
ORD
Chicago
$301 Roundtrip, found 5 days ago
$301
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 25 from Portland to Chicago, returning Tue, Apr 28, priced at $301 found 5 days ago

Find the cheapest month to fly from Portland (PDX) to Chicago (ORD)

August is typically the cheapest month to fly

From $105 - $269 per traveler.

Travel information

Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Popular airline
Alaska Airlines
Distance
2774 km
Average flight time
6 hours 4 mins

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