✓Good DealAiFly Score: 43/100Verified 21 Apr 2026 18:17 UTC
Chicago to Portland with AA from $195.
✓ Verified DealJust published
Tickets from $195 both ways. Checked baggage is not included in the base fare.
📖 Traveler Resources:
✈️ PDX Airport Terminal Guide
✈️ PDX Airport Terminal Guide
Available Dates
Select a date to check live prices on Skyscanner.
26 May – 3 Jun$195✈︎ 4h 36m · DirectSkyscanner →
2 Jun – 10 Jun$195✈︎ 4h 36m · DirectSkyscanner →
18 Aug – 26 Aug$195✈︎ 4h 36m · DirectSkyscanner →
25 Aug – 2 Sep$195✈︎ 4h 36m · DirectSkyscanner →
1 Sep – 9 Sep$195✈︎ 4h 36m · DirectSkyscanner →
8 Sep – 16 Sep$195✈︎ 4h 36m · DirectSkyscanner →
Prices verified at time of publication. Always confirm on Skyscanner before booking.
🌍 About Portland
Discover Portland — one of the world's most captivating destinations, offering unforgettable experiences for every type of traveller.
