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Chicago ✈ Portland

Cheapest airfares from Chicago to Portland

Search for flight deals to Portland

*All prices in AUD, prices may fluctuate slightly from the advertised price.
Fly on Sat, May 2nd 2026
From $254

Southwest Airlines
WN 3579 (1 Transfer)
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Fly on Thu, Apr 9th 2026
From $374

Hawaiian Airlines
HA 6293 (1 Transfer)
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