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From Chicago
Current:
Chicago to Portland
Chicago ✈ Portland
Cheapest airfares from Chicago to Portland
Search for flight deals to Portland
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All prices in AUD, prices may fluctuate slightly from the advertised price.
Fly on Sun, May 24th 2026
From
$138
American Airlines
AA 1317 (Direct)
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Fly on Sun, Mar 1st 2026
From
$140
American Airlines
AA 1937 (Direct)
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Fly on Fri, Apr 17th 2026
From
$165
Frontier Airlines
F9 2145 (1 Transfer)
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Fly on Sat, Mar 28th 2026
From
$172
Southwest Airlines
WN 1394 (1 Transfer)
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Fly on Thu, Jul 23rd 2026
From
$255
Alaska Airlines
AS 413 (Direct)
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