$185 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 5/19. 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$281
Eugene
Eugene1 stop$367
Redmond
Redmond2 stops$429
Medford
Medford1 stop$369
Boise
Boise1 stop$291
Portland
Portland1 stop$281
Eugene
Eugene1 stop$367
Redmond
Redmond2 stops$429
Medford
Medford1 stop$369
Boise
Boise1 stop$291

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

jue., abr. 16 - sáb., abr. 18
Frontier Logo
2:37 pm - 11:03 am
MSN
-
PDX
22h 26m
1 stop
Frontier Logo
12:27 pm - 1:52 pm
PDX
-
MSN
23h 25m
1 stop
$281Frontier
sáb., abr. 25 - sáb., may. 2
United Airlines Logo
4:15 pm - 9:34 pm
MSN
-
BOI
6h 19m
1 stop
United Airlines Logo
2:33 pm - 8:55 pm
BOI
-
MSN
5h 22m
1 stop
$291United Airlines
sáb., abr. 25 - sáb., may. 2
United Airlines Logo
12:13 pm - 9:34 pm
MSN
-
BOI
10h 21m
2 stops
United Airlines Logo
2:33 pm - 8:55 pm
BOI
-
MSN
5h 22m
1 stop
$296United Airlines
mié., abr. 22 - sáb., abr. 25
United Airlines Logo
4:15 pm - 9:22 pm
MSN
-
BOI
6h 07m
1 stop
United Airlines Logo
10:35 am - 9:21 pm
BOI
-
MSN
9h 46m
2 stops
$314United Airlines
mié., abr. 15 - jue., abr. 30
Delta Logo
6:00 am - 4:14 pm
MSN
-
BOI
11h 14m
2 stops
Delta Logo
8:40 pm - 10:09 am
BOI
-
MSN
12h 29m
2 stops
$330Delta
mié., abr. 15 - sáb., abr. 18
American Airlines Logo
5:30 am - 12:49 pm
MSN
-
BOI
8h 19m
1 stop
American Airlines Logo
1:53 pm - 10:32 pm
BOI
-
MSN
7h 39m
1 stop
$345American Airlines
jue., jul. 23 - vie., jul. 31
Delta Logo
6:00 am - 10:57 am
MSN
-
BOI
5h 57m
1 stop
Delta Logo
5:20 am - 11:19 am
BOI
-
MSN
4h 59m
1 stop
$349Delta
vie., abr. 24 - lun., abr. 27
American Airlines Logo
3:29 pm - 11:54 pm
MSN
-
PDX
10h 25m
1 stop
American Airlines Logo
12:59 am - 11:05 am
PDX
-
MSN
8h 06m
1 stop
$368American Airlines
mar., abr. 28 - sáb., may. 2
Alaska Airlines Logo
3:01 pm - 11:59 pm
MSN
-
EUG
10h 58m
2 stops
Alaska Airlines Logo
8:38 pm - 8:45 am
EUG
-
MSN
10h 07m
2 stops
$401Alaska Airlines
sáb., may. 2 - lun., may. 4
Alaska Airlines Logo
5:00 am - 12:52 pm
MSN
-
MFR
9h 52m
2 stops
Alaska Airlines Logo
7:41 pm - 9:48 am
MFR
-
MSN
12h 07m
2 stops
$449Alaska 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 April.

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 $509 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 3 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$185
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 8359 reviews
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

8.0 ExcellentLorna, Mar 2026
LAX - LIH
Read more Delta reviews

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

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.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

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

Information on your arrival and departure airports