There are most likely no direct flights on the Chicago — Portland route
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A non-stop flight is the most convenient and comfortable way to fly from Chicago to Portland, despite the fact that sometimes flights with transfers can cost significantly less.
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There are most likely no direct flights on the Chicago — Portland route
The cost of a one-way flight from Chicago to Portland ranges from $132 (September 2026) to $181 (October 2026). On average, the ticket price is about $154–$331.
Flight costs from Chicago to Portland climb toward the middle of the period, then start to drop. By choosing the right dates, you can save noticeably.
Prices rise from September 2026 to October 2026 (+37%), then decline from October 2026 to December 2026 (17%). The cheapest tickets are in September 2026–October 2026 (averaging $157), while the priciest are in October 2026–December 2026 ($166).
For savings, plan your flight for September 2026–October 2026 — you could save up to 6%. Try to avoid October 2026–December 2026 when possible: prices are at their highest then.
Price spread on this route is 13.1%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.
Chicago — Portland
09/14/2026
Departure
Direct flight
WN265
starting at $288
Chicago — Portland
09/14/2026
Departure
Direct flight
UA1554
starting at $210
Chicago — Portland
12/15/2026
Departure
Direct flight
AA562
starting at $307
Chicago — Portland
09/09/2026
Departure
Direct flight
UA1554
starting at $235
Chicago — Portland
09/10/2026
Departure
Direct flight
AS325
starting at $303
Chicago — Portland
09/11/2026
Departure
Direct flight
UA2300
starting at $234
Chicago — Portland
09/17/2026
Departure
Direct flight
WN806
starting at $281
Chicago — Portland
10/12/2026
Departure
Direct flight
WN738
starting at $273
starting at $181
starting at $210
starting at $307
starting at $134
starting at $172
More than 5 airlines operate flights from Chicago to Portland, including Southwest Airlines, United Airlines, American Airlines, Alaska Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $134, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
The cheapest flight ticket from Chicago to Portland according to data for the last 48 hours costs $134
Often the best time to buy tickets from Chicago to Portland is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Portland can be found flying in these months: September, December, October.
The fastest flights from Chicago to Portland start from 4 hours 20 minutes in the air.
The following airlines operate direct flights on the route Chicago — Portland: Southwest Airlines, United Airlines, American Airlines
The cheapest one-way flight from Chicago to Portland departs on 09/10/2026, is operated by Alaska Airlines and costs $134
The cheapest roundtrip flight from Chicago to Portland departs on 10/16/2026, is operated by Frontier Airlines and costs $275
Fastest flight from Chicago to Portland takes 4h 20m
There are direct flights on this route 5 days a week: Mo, Tu, We, Th, and Fr
The distance between Chicago and Portland is 2816km (1746 miles). The average flight duration is 4h 25m. There are 22 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 2h. Flights from Chicago begin at 9:55 AM. The latest flight from Chicago departs at 9:50 PM
