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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 Portland to Chicago. 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 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.
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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Portland — Chicago
05/04/2026
Departure
Direct flight
WN1162
starting at $354
Portland — Chicago
05/05/2026
Departure
Direct flight
WN1162
starting at $389
Portland — Chicago
05/07/2026
Departure
Direct flight
UA2019
starting at $345
Portland — Chicago
05/13/2026
Departure
Direct flight
AA2197
starting at $242
Portland — Chicago
06/22/2026
Departure
Direct flight
AA2933
starting at $304
starting at $354
starting at $223
starting at $242
starting at $159
starting at $218
The Portland — Chicago route is served by a wide range of airlines: 5 in total, including Southwest Airlines, United Airlines, American Airlines, Alaska Airlines, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $159. 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 one-way flight from Portland to Chicago departs on 06/23/2026, is operated by Alaska Airlines and costs $159
The cheapest roundtrip flight from Portland to Chicago departs on 06/11/2026, is operated by Frontier Airlines and costs $278
Fastest flight from Portland to Chicago takes 4h 1m
There are direct flights on this route 4 days a week: Mo, Tu, We, and Th
The distance between Portland and Chicago is 2816km (1746 miles). The time difference between Portland and Chicago is 2h
We couldn't find any special offers for flights from Portland to Chicago
The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $159
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: June, May.
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: Southwest Airlines, United Airlines, American Airlines
The minimum one-way ticket price from Portland to Chicago is $159 (June 2026), while the maximum is $218 (May 2026). On average, a ticket costs $189–$218.