There are most likely no direct flights on the Portland — Chicago route
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A non-stop flight is the most convenient and comfortable way to fly from Portland to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the Portland — Chicago route
The minimum one-way ticket price from Portland to Chicago is $159 (December 2026), while the maximum is $1,326 (August 2027). On average, a ticket costs $186–$462.
The Portland — Chicago route shows a classic seasonal pattern: prices rise, peak, then fall again. Knowing this, you can pick a more affordable time to fly.
Prices rise from December 2026 to August 2027 (+732%), then decline from September 2026 to December 2026 (14%). The cheapest tickets are in October 2026–December 2026 (averaging $168), while the priciest are in December 2026–August 2027 ($743).
For savings, plan your flight for October 2026–December 2026 — you could save up to 77%. Try to avoid December 2026–August 2027 when possible: prices are at their highest then.
Price spread on this route is 107.9%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.
Portland — Chicago
09/16/2026
Departure
Direct flight
AA1713
starting at $244
Portland — Chicago
10/04/2026
Departure
Direct flight
UA2094
starting at $193
Portland — Chicago
10/06/2026
Departure
Direct flight
WN1567
starting at $235
Portland — Chicago
09/16/2026
Departure
Direct flight
WN3131
starting at $230
starting at $244
starting at $149
starting at $230
starting at $169
The Portland — Chicago route is served by a wide range of airlines: 4 in total, including American Airlines, United Airlines, Southwest Airlines, and Alaska Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $149. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $149
Often the best time to buy tickets from Portland to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Portland to Chicago can be found flying in these months: December, October, September.
The fastest flights from Portland to Chicago start from 4 hours 1 minute in the air.
The following airlines operate direct flights on the route Portland — Chicago: American Airlines, United Airlines, Southwest Airlines
The cheapest one-way flight from Portland to Chicago departs on 09/17/2026, is operated by United Airlines and costs $149
There is no information about the cheapest roundtrip flight from Portland to Chicago
Fastest flight from Portland to Chicago takes 4h 1m
There are direct flights on this route 3 days a week: Su, Tu, and We
The distance between Portland and Chicago is 2816km (1746 miles). There are 91 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 2h. Flights from Portland begin at 6:00 AM. The latest flight from Portland departs at 11:40 PM
We couldn't find any special offers for flights from Portland to Chicago
