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Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Portland. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
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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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
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The cost of a one-way flight from Chicago to Portland ranges from $127 (June 2026) to $153 (May 2026). On average, the ticket price is about $140–$153.
Chicago — Portland
05/08/2026
Departure
Direct flight
UA1994
starting at $384
Chicago — Portland
05/11/2026
Departure
Direct flight
UA1531
starting at $323
Chicago — Portland
05/23/2026
Departure
Direct flight
UA630
starting at $184
Chicago — Portland
06/11/2026
Departure
Direct flight
WN2809
starting at $344
Chicago — Portland
05/03/2026
Departure
Direct flight
UA1531
starting at $439
Chicago — Portland
05/04/2026
Departure
Direct flight
AS325
starting at $381
Chicago — Portland
05/06/2026
Departure
Direct flight
UA1531
starting at $383
Chicago — Portland
05/07/2026
Departure
Direct flight
UA1531
starting at $380
starting at $184
starting at $344
starting at $381
starting at $127
starting at $381
More than 5 airlines operate flights from Chicago to Portland, including United Airlines, Southwest Airlines, Alaska Airlines, Frontier Airlines, and American Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $127, 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 $127
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: June, May.
The fastest flights from Chicago to Portland start from 4 hours 32 minutes in the air.
The following airlines operate direct flights on the route Chicago — Portland: United Airlines, Southwest Airlines, Alaska Airlines
The cheapest one-way flight from Chicago to Portland departs on 06/11/2026, is operated by Frontier Airlines and costs $127
The cheapest roundtrip flight from Chicago to Portland departs on 05/30/2026, is operated by Frontier Airlines and costs $122
Fastest flight from Chicago to Portland takes 4h 32m
There are direct flights on this route 6 days a week: Su, Mo, We, Th, Fr, and Sa
The distance between Chicago and Portland is 2816km (1746 miles). There are 6 direct flights from Chicago to Portland. The time difference between Chicago and Portland is 2h. Flights from Chicago begin at 8:15 AM. The latest flight from Chicago departs at 9:44 PM
We couldn't find any special offers for flights from Chicago to Portland
