$119 Find Cheap Flights from Chicago Midway Airport to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Oregon departing on 1/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oregon, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$227
Eugene
Eugene2 stops$299
Redmond
Redmond2 stops$389
Medford
Medford2 stops$2,711
Boise
Boise1 stop$269
Portland
Portland1 stop$227
Eugene
Eugene2 stops$299
Redmond
Redmond2 stops$389
Medford
Medford2 stops$2,711
Boise
Boise1 stop$269

Book Cheap Midway to Oregon Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Oregon that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Oregon

Sat, Jan 10 - Sat, Jan 17
Southwest Logo
12:40 pm - 7:55 pm
MDW
-
PDX
9h 15m1 stop
Southwest Logo
6:00 am - 11:55 am
PDX
-
MDW
3h 55mnonstop
$227Southwest
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
4:05 pm - 8:30 pm
MDW
-
PDX
6h 25m1 stop
Southwest Logo
12:45 pm - 8:30 pm
PDX
-
MDW
5h 45m1 stop
$236Southwest
Wed, Jan 7 - Wed, Jan 14
Delta Logo
1:49 pm - 8:12 pm
MDW
-
PDX
8h 23m1 stop
Delta Logo
11:44 am - 10:07 pm
PDX
-
MDW
8h 23m1 stop
$237Delta
Tue, Jan 6 - Thu, Jan 15
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
5:35 am - 5:00 pm
PDX
-
MDW
9h 25m2 stops
$242Southwest
Tue, Jan 6 - Thu, Jan 15
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
6:45 am - 12:40 pm
PDX
-
MDW
3h 55mnonstop
$243Southwest
Wed, Jan 7 - Thu, Jan 8
Southwest Logo
3:40 pm - 10:05 pm
MDW
-
PDX
8h 25m1 stop
Southwest Logo
2:15 pm - 10:50 pm
PDX
-
MDW
6h 35m1 stop
$246Southwest
Tue, Jan 6 - Thu, Jan 8
Southwest Logo
3:35 pm - 6:00 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
11:05 am - 7:55 pm
PDX
-
MDW
6h 50m1 stop
$247Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
8:10 am - 3:40 pm
MDW
-
PDX
9h 30m2 stops
Southwest Logo
6:30 am - 12:25 pm
PDX
-
MDW
3h 55mnonstop
$252Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
12:05 pm - 2:30 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
6:45 am - 12:40 pm
PDX
-
MDW
3h 55mnonstop
$253Southwest
Thu, Jan 22 - Sun, Jan 25
Delta Logo
6:00 am - 12:30 pm
MDW
-
BOI
7h 30m1 stop
Delta Logo
5:20 am - 1:09 pm
BOI
-
MDW
6h 49m1 stop
$269Delta
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.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Oregon from Chicago Midway Airport found in the last 72 hours was to Portland, at $273 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 72 hours was $273.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $313, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Oregon, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Oregon is January, when tickets cost $238 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $637 and $567 respectively.

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

The average price of all round-trip flights from Chicago Midway Airport to Oregon clicked on KAYAK for each day over the last 12 months.

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

Find deals

Good to know

Low seasonSeptember
Cheapest flight$119
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to Portland

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.

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

    The cheapest time of day to fly to Oregon is generally at night, when round-trip flights cost $328 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the evening, which is peak travel time and where the average cost of a ticket is $402.

Reviews of the top airline flying from Midway to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4250 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything you need to know for your flight from Midway to Oregon

Information on your arrival and departure airports

Chicago Midway Airport (MDW)