Southwest Airlines
Every day
starting at $230
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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The minimum one-way ticket price from Portland to Chicago is $174 (December 2026), while the maximum is $177 (November 2026). On average, a ticket costs $176–$177.
Southwest Airlines
Every day
starting at $230
The only airline operating direct flights from Portland to Chicago is Southwest Airlines. Flights operate every day.
Portland — Chicago
12/18/2026
Departure
Direct flight
AA3329
starting at $174
Portland — Chicago
11/10/2026
Departure
Direct flight
AA562
starting at $190
Portland — Chicago
11/13/2026
Departure
Direct flight
AA519
starting at $193
Portland — Chicago
11/20/2026
Departure
Direct flight
UA2266
starting at $261
Portland — Chicago
11/08/2026
Departure
Direct flight
AA428
starting at $192
Portland — Chicago
11/15/2026
Departure
Direct flight
AA519
starting at $266
The route Portland — Chicago is served by several airlines: American Airlines, United Airlines, and Frontier Airlines. This gives passengers more freedom in choosing flights. You can consider not only the price but also schedules, baggage policies, and onboard service. Our service compares all offers so you can find tickets from $174 and choose the most convenient option. Thanks to airline competition, you may also find promotional fares or special offers, helping you save even more. Plan your trip in advance and choose the best flights without overpaying.
The cheapest flight ticket from Portland to Chicago according to data for the last 48 hours costs $174
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, November.
The fastest flights from Portland to Chicago start from 3 hours 54 minutes in the air.
The following airlines operate direct flights on the route Portland — Chicago: American Airlines, United Airlines
The cheapest one-way flight from Portland to Chicago departs on 12/18/2026, is operated by American Airlines and costs $174
The cheapest roundtrip flight from Portland to Chicago departs on 11/22/2026, is operated by Southwest Airlines and costs $267
Fastest flight from Portland to Chicago takes 3h 54m
There are direct flights on this route 3 days a week: Su, Tu, and Fr
The distance between Portland and Chicago is 2823km (1750 miles). There are 38 direct flights from Portland to Chicago. The time difference between Portland and Chicago is 2h. Flights from Portland begin at 5:20 AM. The latest flight from Portland departs at 11:35 PM
