$90 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 8/30. 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

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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Cheap Flights from Midway to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$179
Eugene
Eugene1 stop$311
Redmond
Redmond2 stops$289
Medford
Medford2 stops$319
Boise
Boise1 stop$215
Portland
Portlandnonstop$179
Eugene
Eugene1 stop$311
Redmond
Redmond2 stops$289
Medford
Medford2 stops$319
Boise
Boise1 stop$215

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, Aug 30 - Sun, Aug 31
Southwest Logo
2:10 pm - 4:25 pmMDW-PDX
4h 15mnonstop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$179Southwest
Find Deal
Tue, Aug 26 - Sun, Aug 31
Southwest Logo
8:30 pm - 10:45 pmMDW-PDX
4h 15mnonstop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$188Southwest
Find Deal
Sat, Aug 30 - Sun, Aug 31
Southwest Logo
11:40 am - 8:35 pmMDW-PDX
10h 55m1 stop
Southwest Logo
6:55 am - 12:55 pmPDX-MDW
4h 00mnonstop
$189Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
8:30 am - 10:50 amMDW-PDX
4h 20mnonstop
Southwest Logo
9:20 am - 3:15 pmPDX-MDW
3h 55mnonstop
$197Southwest
Find Deal
Sat, Oct 25 - Thu, Oct 30
Delta Logo
6:00 am - 12:59 pmMDW-PDX
8h 59m1 stop
Delta Logo
12:50 am - 8:55 amPDX-MDW
6h 05m1 stop
$208Delta
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Sat, Sep 6 - Sat, Sep 13
Delta Logo
7:17 pm - 11:56 pmMDW-BOI
5h 39m1 stop
Delta Logo
5:25 am - 1:03 pmBOI-MDW
6h 38m1 stop
$215Delta
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
9:15 am - 2:01 pmMDW-BOI
5h 46m1 stop
Delta Logo
5:30 am - 1:03 pmBOI-MDW
6h 33m1 stop
$216Delta
Find Deal
Fri, Aug 15 - Sat, Aug 16
Frontier Logo
12:35 pm - 12:15 amMDW-PDX
13h 40m1 stop
Frontier Logo
7:01 pm - 8:54 pmPDX-MDW
23h 53m1 stop
$257Frontier
Find Deal
Fri, Sep 5 - Sun, Sep 7
Frontier Logo
4:48 pm - 12:12 amMDW-PDX
9h 24m1 stop
Frontier Logo
10:27 am - 9:58 pmPDX-MDW
9h 31m1 stop
$258Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17
Frontier Logo
2:44 pm - 12:16 amMDW-PDX
11h 32m1 stop
Frontier Logo
6:35 am - 11:41 amPDX-MDW
27h 06m1 stop
$265Frontier
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Oregon.

The cheapest ticket to Oregon from Chicago Midway Airport found in the last 72 hours was to Portland, at $105 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 $105.

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 $275, 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 $266 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $593 and $555 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 Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.


Good to know

Low seasonMarch
Cheapest flight$90
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 15% 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 in the morning, when round-trip flights cost $330 on average. Morning departures are around 20% 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 $413.

Reviews of the top airlines 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.
8.0
SouthwestOverall score based on 4241 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

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

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