Cheap flights from Chicago to Portland from $109

The cheapest month to fly to Portland from Chicago 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 Chicago, 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 Chicago - Portland flight prices

You are more likely to see cheaper flights to Portland from Chicago 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 Chicago for as low as $277 on momondo.

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

No. A direct flight is the cheapest option for a flight between Chicago to Portland.

As of February 2026, prices for Chicago to Portland flights are approximately 27% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Portland from Chicago according to our data. United Airlines is the first choice among our users, with 38% 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.

Las Vegas (LAS) was the most common stop: 55% of momondo users choosing 1-stop flights on this route connected there.

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $173.

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 9h 46m.

Las Vegas (LAS) has the shortest average layover time for this route: 3h 40m.

The number of flights available between Chicago and Portland is 15 per day as of February 2026. The most frequent departure time is 4:00PM, with 69% of daily flights leaving in the afternoon.

As of February 2026, there are 108 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Fri, with 18% of flights taking off on this day.