$135 Find Cheap Flights from Madison 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 Madison to Oregon departing on 4/26. 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 Madison 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 Madison to Oregon, as well as popular online travel agencies
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Cheap Flights from Madison to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$261
Eugene
Eugene1 stop$389
Redmond
Redmond1 stop$508
Medford
Medford1 stop$449
Boise
Boise1 stop$349
Portland
Portland1 stop$261
Eugene
Eugene1 stop$389
Redmond
Redmond1 stop$508
Medford
Medford1 stop$449
Boise
Boise1 stop$349

Book Cheap Madison 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 Madison 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 Madison to Oregon

Sat, Jun 6 - Sat, Jun 13
Frontier Logo
7:59 pm - 4:46 pm
MSN
-
PDX
22h 47m
1 stop
Frontier Logo
12:26 pm - 7:09 pm
PDX
-
MSN
28h 43m
1 stop
$261Frontier
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:15 am - 12:54 pm
MSN
-
PDX
8h 39m
1 stop
Delta Logo
11:39 am - 9:57 pm
PDX
-
MSN
8h 18m
1 stop
$321Delta
Tue, Aug 11 - Wed, Aug 19
United Airlines Logo
10:49 am - 5:43 pm
MSN
-
PDX
8h 54m
2 stops
United Airlines Logo
7:00 am - 2:53 pm
PDX
-
MSN
5h 53m
1 stop
$326United Airlines
Wed, Aug 19 - Wed, Aug 26
United Airlines Logo
5:00 am - 9:29 am
MSN
-
PDX
6h 29m
1 stop
United Airlines Logo
2:15 pm - 12:04 am
PDX
-
MSN
7h 49m
1 stop
$336United Airlines
Tue, Aug 11 - Tue, Aug 18
United Airlines Logo
10:49 am - 5:43 pm
MSN
-
PDX
8h 54m
2 stops
United Airlines Logo
7:00 am - 2:53 pm
PDX
-
MSN
5h 53m
1 stop
$341United Airlines
Fri, May 29 - Tue, Jun 2
Multiple Airlines Logo
9:10 am - 11:50 am
MSN
-
PDX
28h 40m
1 stop
Multiple Airlines Logo
5:46 pm - 9:14 am
PDX
-
MSN
13h 28m
2 stops
$358Multiple Airlines
Mon, May 25 - Sat, May 30
American Airlines Logo
5:00 am - 9:59 am
MSN
-
PDX
6h 59m
1 stop
American Airlines Logo
11:43 pm - 10:38 am
PDX
-
MSN
8h 55m
1 stop
$366American Airlines
Wed, Jul 1 - Wed, Jul 8
American Airlines Logo
5:11 pm - 12:50 am
MSN
-
PDX
9h 39m
1 stop
American Airlines Logo
10:57 pm - 7:49 am
PDX
-
MSN
6h 52m
1 stop
$367American Airlines
Wed, Jul 22 - Thu, Jul 30
Alaska Airlines Logo
5:00 am - 11:53 am
MSN
-
MFR
8h 53m
2 stops
Alaska Airlines Logo
7:35 pm - 7:49 am
MFR
-
MSN
10h 14m
2 stops
$507Alaska Airlines
Wed, Jul 22 - Thu, Jul 30
Alaska Airlines Logo
5:00 am - 11:53 am
MSN
-
MFR
8h 53m
2 stops
Alaska Airlines Logo
7:35 pm - 7:49 am
MFR
-
MSN
10h 14m
2 stops
$539Alaska Airlines
Booking Insights

KAYAK's insights & trends for Madison to Oregon flights

Get data-powered insights and trends into flights from Madison 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 Madison to Oregon?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to Oregon departing in June.

What is the cheapest Madison to Oregon flight route?

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

The cheapest ticket to Oregon from Madison found in the last 72 hours was to Portland, at $424 round-trip. The most popular route is from Madison (MSN) to Eugene (EUG), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $469.

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

The average price for all round-trip flights from Madison to Oregon depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Oregon is generally in the morning, when round-trip flights cost $369 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 $369.

Can I save money by flying with a layover from Madison 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 $515, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison 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 Madison to Oregon is February, when tickets cost $347 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $543 and $483 respectively.

How far in advance should I book a flight from Madison to Oregon?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Oregon, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Oregon, you should book around 4 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$135
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from Madison to Portland

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Madison 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 Madison to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison 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 Madison 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 Madison 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 Madison 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 Madison 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 4 airlines serving from Madison to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Madison 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 Madison 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
DeltaOverall score based on 8409 reviews
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

The tray table was broken and the food was terrible.

4.0 OkayJeremy, Apr 2026
BNA - BOS
Read more Delta reviews

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

Overall flight was ok. Flight attendant was receptive to assisting passengers with tight connections.

Checking in united could not figure out my star alliance gold. Baggage did not get marked priority and didn't receive boarding passes. When got to SFO lounge personal fixed everything Immediately

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

The flight was on time and the landing was very smooth. The crew and flight attendants were all very friendly and professional.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

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

Information on your arrival and departure airports