Cheap Flights from Chicago to Oregon from £102 Return

Flight deals from Chicago to Oregon

Looking for cheap tickets from Chicago to Oregon, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Portland.£102 per passenger.Departing Sun, 7 Dec, returning Thu, 11 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 7 Dec, arriving in Portland.Inbound indirect flight with Frontier Airlines, departs from Portland on Thu, 11 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From £102, select.

Eugene.£203 per passenger.Departing Fri, 5 Dec, returning Sun, 7 Dec.Return flight with Frontier Airlines and Alaska Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 5 Dec, arriving in Eugene.Inbound indirect flight with Alaska Airlines, departs from Eugene on Sun, 7 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From £203, select.

Redmond.£225 per passenger.Departing Mon, 2 Feb, returning Sat, 7 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 2 Feb, arriving in Redmond.Inbound indirect flight with Delta, departs from Redmond on Sat, 7 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £225, select.

Medford.£320 per passenger.Departing Fri, 28 Nov, returning Tue, 2 Dec.Return flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Fri, 28 Nov, arriving in Medford.Inbound indirect flight with Alaska Airlines, departs from Medford on Tue, 2 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From £320, select.

North Bend.£694 per passenger.Departing Sun, 7 Jun, returning Fri, 12 Jun.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sun, 7 Jun, arriving in North Bend.Inbound indirect flight with United, departs from North Bend on Fri, 12 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From £694, select.

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Flying from Chicago to Oregon

Arm yourself with these facts on the fly.

Cheapest flight found	£102
Cheapest month to fly	December
Average flight time	4 hrs, 32 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

How to find cheap flights from Chicago to Oregon

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Oregon. Other savvy travellers recently found return flights from £102 and one-way tickets from £52 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Portland

At the moment, the lowest priced flight tickets to Oregon are from Chicago O'Hare International Airport to Portland Airport.

Fly in December

We crunched the flight calendar and found the cheapest time to fly from Chicago to Oregon is currently December.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Oregon.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Oregon go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Oregon to Oregon flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Oregon flight price?

We looked at all of the upcoming return flights from Chicago to Oregon we could find over the next 12 months. It looks like £102 is the best price. This is good, compared to the average Oregon ticket price of £309.

What is the cheapest month to fly from Chicago to Oregon?

The cheapest month to fly from Chicago to Portland Airport is usually December. The cheapest month to fly from Chicago to Medford Airport is usually November. The cheapest month to fly from Chicago to Redmond Airport is usually February. And the cheapest month to fly from Chicago to North Bend Airport is usually June.