Cheap flights from Chicago to Oregon from $116

The month of February is, on average, the cheapest month to fly to Oregon from Chicago, with most prices found around $305. The month of January is another great option to travel to Oregon, with average flight prices from Chicago averaging around $313.

On average, the least expensive day to fly to Oregon from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $357. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Oregon is Sunday, with ticket prices averaging around $443.

According to our data, the cheapest time of day to fly to Oregon is in the evening. momondo users have found flights departing from Chicago to Oregon in the evening for as low as $341. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Oregon are more costly at noon, with an average ticket price of $459. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Oregon from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Oregon for around $358 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Oregon from Chicago for as low as $268 on momondo.

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

Southwest, Alaska Airlines, and Delta are the most popular carriers operating from Chicago to Oregon

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Oregon from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Oregon. Keep in mind that there are 7 different airlines that fly to Oregon on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 25 flights per day flying from Chicago to Oregon. The most common time of day flights depart is 4:00PM, with 42% of flights taking off in the afternoon.

181 flights are operational weekly from Chicago to Oregon as of September 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.