$146 Find Cheap Flights from Chicago Midway Airport to Oregon - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Portland
Portland2 stops$359
Eugene
Eugene1 stop$345
Redmond
Redmond2 stops$561
Medford
Medford2 stops$575
Boise
Boise1 stop$313
Portland
Portland2 stops$359
Eugene
Eugene1 stop$345
Redmond
Redmond2 stops$561
Medford
Medford2 stops$575
Boise
Boise1 stop$313
Booking Insights

KAYAK's insights & trends for Midway to Oregon flights

Get data-powered insights and trends into flights from Midway to Oregon to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to Oregon?

Flight prices are below average for this route right now.

Flights to Oregon from Chicago Midway Airport usually cost between $360 and $371 in January.
The lowest price found in the past 5 days was $359 on Delta (Jan 21-Jan 24).

What is the cheapest Chicago Midway Airport to Oregon flight route?

The cheapest ticket to Oregon from Chicago Midway Airport found in the last 5 days was to Portland, at $317 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Portland (PDX), and the cheapest round-trip airline ticket found on this route in the last 5 days was $317.

What is the cheapest time of day to fly to Oregon?

The cheapest time of day to fly to Oregon is generally in the evening, when round-trip flights cost $338 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the morning, which is peak travel time and where the average cost of a ticket is $386.

Can I save money by flying with a layover from Chicago Midway Airport to Oregon?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $365 on average.

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

The cheapest month for flights from Chicago Midway Airport to Oregon is March, when tickets cost $227 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $538 and $431 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Oregon?

Your flight ticket price will generally be cheaper if you fly to Oregon on a Sunday and more expensive on a Wednesday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

Good to know

Low season

January

Cheapest flight

$146
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago Midway Airport to Eugene

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Oregon?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Oregon?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Oregon?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Oregon

 
Need help choosing which airline to fly with from Midway to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4217 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.4Entertainment
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Long layover in Chicago. Wish that could have been lessened.

More options for your flight from Midway to Oregon

Complete your trip to Oregon with a hotel stay or car rental