✓Good DealAiFly Score: 45/100Verified 9 Jun 2026 18:53 UTC
Chicago to Portland with American Airlines from $195.
✓ Verified Deal
Tickets from $195 both ways. Checked baggage is not included in the base fare.
✈️ American Airlines — AFR 53/100 (premium-light-strict)
In this fare:
- Checked baggage: Not included — paid checked baggage extra
- Onboard meal: Snack
- WiFi: Paid wifi
- Cabin: 30″ pitch on 737-800
Available Dates
Select a date to check live prices on Skyscanner.
📅 26 May → 3 Jun — date has passed. See current deals from Chicago.
📅 2 Jun → 10 Jun — date has passed. See current deals from Chicago.
18 Aug – 26 Aug$195Skyscanner →
25 Aug – 2 Sep$195Skyscanner →
1 Sep – 9 Sep$195Skyscanner →
8 Sep – 16 Sep$195Skyscanner →
Prices verified at time of publication. Always confirm on Skyscanner before booking.
🌍 About Portland
Portland's signature isn't a monument — it's the absence of sales tax, so the price on the shelf is the price you pay, which makes Powell's City of Books a genuine event: a full city block of new and used titles, color-coded rooms, the largest independent bookstore in the US. Eat marionberry anything (pie, jam, ice cream) — the marionberry is a blackberry bred at Oregon State in the 1940s and grown almost nowhere else. The food carts, clustered in "pods" across downtown and the east side, are the real dinner move, not the sit-down restaurants. Come July through September: it's reliably dry and warm, and Forest Park and the Columbia Gorge waterfalls are at their best. The rest of the year earns Portland its gray, drizzly reputation — mild but relentlessly wet from November to May.
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