PDX - MSN

$107 Find Cheap Flights from Portland to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Madison departing on 11/13. 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 Madison

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

Cheap Flights from Portland to Madison (PDX-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Madison 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 Portland to Madison

Fri, Feb 27 - Wed, Mar 4
Delta Logo
12:55 am - 10:06 amPDX-MSN
7h 11m1 stop
Delta Logo
10:55 am - 4:51 pmMSN-PDX
7h 56m1 stop
$314Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
1:51 pm - 11:01 pmPDX-MSN
7h 10m1 stop
American Airlines Logo
7:35 am - 1:39 pmMSN-PDX
8h 04m1 stop
$369American Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
United Airlines Logo
12:55 pm - 9:03 pmPDX-MSN
6h 08m1 stop
United Airlines Logo
3:58 pm - 10:36 pmMSN-PDX
8h 38m1 stop
$371United Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
United Airlines Logo
7:00 am - 2:54 pmPDX-MSN
5h 54m1 stop
United Airlines Logo
6:30 am - 2:46 pmMSN-PDX
10h 16m2 stops
$374United Airlines
Find Deal
Sat, Feb 28 - Wed, Mar 4
Delta Logo
6:00 am - 10:08 pmPDX-MSN
14h 08m2 stops
Delta Logo
10:55 am - 4:51 pmMSN-PDX
7h 56m1 stop
$377Delta
Find Deal
Wed, Nov 12 - Tue, Nov 18
Alaska Airlines Logo
1:38 pm - 9:50 amPDX-MSN
18h 12m2 stops
Alaska Airlines Logo
10:20 am - 12:09 amMSN-PDX
15h 49m2 stops
$389Alaska Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
12:52 pm - 7:15 pmPDX-MSN
28h 23m1 stop
Frontier Logo
7:59 pm - 7:59 pmMSN-PDX
26h 00m2 stops
$400Frontier
Find Deal
Fri, Feb 27 - Wed, Mar 4
Delta Logo
12:55 am - 10:06 amPDX-MSN
7h 11m1 stop
Delta Logo
6:15 am - 8:47 pmMSN-PDX
16h 32m2 stops
$401Delta
Find Deal
Thu, Nov 20 - Mon, Nov 24
American Airlines Logo
12:59 am - 10:23 amPDX-MSN
7h 24m1 stop
American Airlines Logo
7:35 am - 7:49 pmMSN-PDX
14h 14m1 stop
$487American Airlines
Find Deal
Mon, Dec 29 - Fri, Jan 2
Alaska Airlines Logo
11:00 pm - 9:30 amPDX-MSN
8h 30m1 stop
Alaska Airlines Logo
9:51 am - 4:50 pmMSN-PDX
8h 59m1 stop
$551Alaska Airlines
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $314 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 32% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$314
Overall average: $381
Delta
Fri 2/27Wed 3/4
PDX - MSN • 1 stop
Cheapest one-way
$107
Typical prices: $219-$315
Frontier
Thu 11/13
PDX - MSN • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Booking Insights

KAYAK's insights & trends for Portland to Madison flights

Get data-powered insights and trends into flights from Portland to Madison to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Portland to Madison?

The average price of all round-trip flights from Portland to Madison clicked on KAYAK for each day over the last 12 months.

When flying from Portland to Madison, you should consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Madison, 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 Portland to Madison is January, where tickets cost $310 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $571 and $540 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Madison, 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 Portland to Madison, you should book around 3 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$107
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Portland to Madison

When to book flights from Portland to Madison

Are your dates flexible? Find out the best times to travel from Portland to Madison based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to Madison

  • What is the cheapest flight from Portland to Madison?

    In the last 3 days, the lowest price for a flight from Portland to Madison was $107 for a one-way ticket and $314 for a round-trip.

  • Do I need a passport to fly between Portland and Madison?

    No

  • Which airports will I be using when flying from Portland to Madison?

    When flying out of Portland you will be using Portland. You will be landing at Madison, also known as Madison Truax Field.

  • Which airlines offer Wi-Fi service onboard planes from Portland to Madison?

    Only Delta offers inflight Wi-Fi service on the Portland to Madison flight route.

  • Which aircraft models fly most regularly from Portland to Madison?

    The Airbus A319 is the aircraft model that flies most regularly on the Portland to Madison flight route.

  • Which airline alliances offer flights from Portland to Madison?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Portland and Madison, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Portland to Madison?

    You can catch a nonstop flight from Portland to Madison on on Sunday.

  • Which is the best airline for flights from Portland to Madison, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Portland to Madison are Alaska Airlines and Delta. With an average price for the route of $739 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $447 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Portland to Madison?

    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 Portland to Madison.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Portland 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 Portland to Madison?

    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 to Madison with an airline and back to Portland with another airline. Booking your flights between Portland and MSN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Madison?

    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 to Madison from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Portland to Madison

  • Looking for a cheap flight? 25% of our users found flights on this route for $793 or less round-trip.

Reviews of the top 5 airlines serving from Portland to Madison

 
See real verified KAYAK customer reviews for airlines flying from Portland to Madison. 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 Portland to Madison? 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
Alaska AirlinesOverall score based on 11102 reviews
7.8Comfort
7.0Entertainment
8.5Crew
8.1Boarding
7.1Food
Airline reviews

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

6.0 GoodAnonymous, Oct 2025PDX - MCI
Read more Alaska Airlines reviews

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

One disappointment. There was a gate change from B8 to B10, they had announced it maybe 20 minutes before the boarding time, possibly less. I didn’t hear the announcement as I was listening to music on my head phones at B8. At the boarding time, I got up and asked the gal at the B8 boarding desk, why the destination sign had not changed and if the flight was delayed as there was no plane behind her through the window, she said that perhaps the flight was delayed and the screen will probably update in -5 minutes ( she apparently didn’t know the boarding gate was changed ( 2 down from our location) I put my headphones on and went back to sit down . Just before the B10 door closed, I got a phone call asking me if I was still taking the flight, I said. “Yes” but I was at the gate stated on my ticket B8, then I was informed of the gate change, I got up and ran to the gate, and down the hallway to the jet ramp. I was the last to board!! Very frustrating . I was shocked that I got no emails or text messages from Alaska informing me of a last minute change!!

The crew was the best I’ve ever had HOWEVER when we arrived in Salt Lake City there were no Alaskan Airline employees to be found so we weren’t able to leave the plane until ANOTHER airline took pity on us. How could that possible happen?

The pilot performed the smoothest landing I’ve ever experienced. What a light touch. And I’m an avid traveler!

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

The entertainment available didn’t work for anyone on the flight. Long 6 hr flight with no entertainment option and the staff didn’t know until an hour into the flight when we made sure they knew about it. They had no way to fix it.

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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