Cheap flights from Illinois to Portland from $66

The cheapest month to fly to Portland from Illinois is in January. Flight prices, which tend to average around $257, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until May to fly from Illinois, when ticket prices are also cheap, with an average price of $277.

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $330. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $380.

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $312. At noon is when there is more demand to fly to Portland, so prices are often more expensive at around $447 per ticket.

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

You are more likely to see cheaper flights to Portland from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $325 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Illinois for as low as $277 on momondo.

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

Frontier, Southwest, and Alaska Airlines are the most popular carriers operating from Illinois to Portland

American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to Portland from Illinois according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 7 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

As of February 2026, there are 15 flights per day flying from Illinois to Portland. The most common time of day flights depart is 4:00PM, with 69% of flights taking off in the afternoon.

As of February 2026, 109 flights take off from Illinois and land in Portland each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.