Cheap flights from Portland to Chicago from $166

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $338.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $454. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $561.

Flying to Chicago O'Hare Intl Airport from Portland in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $516. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $398 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland for as low as $309 on momondo.

There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl Airport 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 23% on your flight if you consider stops on a Portland to Chicago O'Hare Intl Airport flight.

As of November 2026, prices for Portland to Chicago O'Hare Intl Airport flights are approximately 13% cheaper when compared to flights at the same time last year.

Alaska Airlines, United Airlines, and Delta are the most popular carriers operating from Portland to Chicago O'Hare Intl

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Portland according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

As of November 2026, 16 flights take off from Portland and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 7:00AM, with 57% of daily flights taking off at noon.

As of November 2026, there are 117 flights per week flying from Portland to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.