Flights from Chicago Midway Airport to Oregon

Flight deals from Chicago Midway Airport to Oregon

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

Portland.Rs24,589 per passenger.Departing Sun, 9 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 9 Nov, arriving in Portland.Price includes taxes and charges.From Rs24,589, select.

Redmond.Rs43,483 per passenger.Departing Sat, 22 Nov.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 22 Nov, arriving in Redmond.Price includes taxes and charges.From Rs43,483, select.

Eugene.Rs47,979 per passenger.Departing Sun, 16 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 16 Nov, arriving in Eugene.Price includes taxes and charges.From Rs47,979, select.

Medford.Rs51,935 per passenger.Departing Wed, 15 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 15 Oct, arriving in Medford.Price includes taxes and charges.From Rs51,935, select.

Pendleton.Rs89,712 per passenger.Departing Thu, 25 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 25 Sep, arriving in Pendleton.Price includes taxes and charges.From Rs89,712, select.

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Flying from Chicago Midway Airport to Oregon

Arm yourself with these facts on the fly.

Cheapest flight found	Rs24,589
Cheapest month to fly	November
Average flight time	4 hrs, 23 mins
Average flights per week	13
Most popular airline	Southwest Airlines

How to find cheap flights from Chicago Midway Airport to Oregon

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago Midway Airport to Oregon. Other savvy travellers recently found return flights from Rs43,268 and one-way tickets from Rs24,750. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in November

The cheapest time to fly from Chicago Midway Airport to Oregon is currently November.

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 Midway Airport 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 Midway Airport to your chosen airport in 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 Airport to Oregon flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

Are there any direct flights from Chicago Midway Airport to Oregon?

Yes - direct flights currently operate from Chicago Midway Airport to Portland Airport in Oregon.

Which other Chicago airports offer direct flights to Oregon?

Chicago O'Hare International Airport offers direct flights to Oregon.

What is the average price of a flight from Chicago Midway Airport to Oregon?

We looked at all of the upcoming return flights from Chicago Midway Airport to Oregon we could find over the next 12 months. It looks like Rs43,268 is the best price. This is good, compared to the average Oregon ticket price of Rs83,561.

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

The cheapest month to fly from Chicago Midway Airport to Medford Airport is currently October.
The cheapest month to fly from Chicago Midway Airport to Redmond Airport is currently October.
The cheapest month to fly from Chicago Midway Airport to Eugene Airport is currently November.
And the cheapest month to fly from Chicago Midway Airport to Portland Airport is usually November.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Oregon on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago Midway Airport to Oregon on Friday, 7 November 2025.

If I'm flying from Chicago Midway Airport, where in Oregon is cheapest to fly into?

If you're flying from Chicago Midway, the cheapest city in Oregon to fly into is Portland. The cheapest airport serving Portland at the moment is Portland.