Cheap flights from Portland to Chicago from $160

The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $272. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Portland to Chicago during February average around $282.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $437. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland to Chicago for around $541.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $381. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $486.

Fly from Portland to Chicago Midway for the best Portland - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $370 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as $309 on momondo.

There are 4 cabin classes available to choose from on Portland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 27% on your flight if you consider stops on a Portland to Chicago flight.

As of August 2026, prices for Portland to Chicago flights are approximately 82% more expensive when compared to flights at the same time last year.

United Airlines, Alaska Airlines, and Southwest are the most popular carriers operating from Portland to Chicago

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Portland according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Portland and Chicago is 19 per day as of August 2026. The most frequent departure time is 12:00PM, with 46% of daily flights leaving at noon.

139 flights are operational weekly from Portland to Chicago as of August 2026. The most popular departure day for this route is Fri, with 21% of flights per week taking off on this day.