$137 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 5/28. 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$251
Eugene
Eugene1 stop$349
Redmond
Redmond2 stops$394
Medford
Medford2 stops$459
Boise
Boise1 stop$329
Portland
Portland1 stop$251
Eugene
Eugene1 stop$349
Redmond
Redmond2 stops$394
Medford
Medford2 stops$459
Boise
Boise1 stop$329

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

Thu, May 28 - Sat, Jun 6
Frontier Logo
7:59 pm - 4:46 pm
MSN
-
PDX
22h 47m
1 stop
Frontier Logo
12:35 pm - 7:14 pm
PDX
-
MSN
28h 39m
1 stop
$251Frontier
Thu, Aug 13 - Mon, Aug 24
Frontier Logo
7:59 pm - 4:53 pm
MSN
-
PDX
22h 54m
1 stop
Frontier Logo
12:26 pm - 7:09 pm
PDX
-
MSN
28h 43m
1 stop
$281Frontier
Wed, Jul 15 - Tue, Jul 21
United Airlines Logo
5:00 am - 9:34 am
MSN
-
PDX
6h 34m
1 stop
United Airlines Logo
11:40 pm - 8:55 am
PDX
-
MSN
7h 15m
1 stop
$321United Airlines
Thu, Jul 2 - Sat, Jul 4
Delta Logo
2:45 pm - 8:55 pm
MSN
-
BOI
7h 10m
1 stop
Delta Logo
2:50 pm - 9:10 pm
BOI
-
MSN
5h 20m
1 stop
$329Delta
Fri, May 29 - Fri, Jun 5
Delta Logo
6:30 am - 11:56 am
MSN
-
BOI
6h 26m
2 stops
Delta Logo
1:53 pm - 10:44 pm
BOI
-
MSN
7h 51m
1 stop
$334Delta
Wed, Jul 29 - Wed, Aug 12
United Airlines Logo
6:30 am - 11:38 am
MSN
-
PDX
7h 08m
1 stop
United Airlines Logo
7:00 am - 2:53 pm
PDX
-
MSN
5h 53m
1 stop
$342United Airlines
Sat, May 30 - Sat, Jun 6
American Airlines Logo
6:45 am - 3:07 pm
MSN
-
BOI
9h 22m
1 stop
American Airlines Logo
1:59 pm - 12:19 am
BOI
-
MSN
9h 20m
1 stop
$364American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
5:46 pm - 11:07 pm
MSN
-
PDX
7h 21m
1 stop
American Airlines Logo
11:20 pm - 9:15 am
PDX
-
MSN
7h 55m
1 stop
$367American Airlines
Fri, Jun 5 - Mon, Jun 8
Alaska Airlines Logo
2:39 pm - 11:59 pm
MSN
-
EUG
11h 20m
2 stops
Alaska Airlines Logo
12:49 pm - 9:20 pm
EUG
-
MSN
30h 31m
2 stops
$459Alaska 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
3:52 pm - 7:51 am
MFR
-
MSN
13h 59m
2 stops
$479Alaska 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 May.

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 August, when tickets cost $114 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $338 and $308 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 26% 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$137
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 7% 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 8459 reviews
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

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!!!

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

Information on your arrival and departure airports