PDX - MSN

$269 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 1/25. 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 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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$289
Overall average: $312
Delta
Thu 1/22Sun 1/25
PDX - MSN • 1 stop
Cheapest one-way
$208
Typical prices: $243-$319
Delta
Sun 1/25
PDX - MSN • 2 stops
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 14% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 31% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
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

Thu, Jan 22 - Sun, Jan 25
Delta Logo
12:40 am - 10:19 am
PDX
-
MSN
7h 39m1 stop
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$289Delta
Fri, Jan 23 - Sun, Jan 25
United Airlines Logo
5:00 am - 7:07 pm
PDX
-
MSN
12h 07m2 stops
United Airlines Logo
6:30 am - 11:57 am
MSN
-
PDX
7h 27m1 stop
$294United Airlines
Fri, Jan 23 - Sun, Jan 25
Delta Logo
5:15 pm - 10:50 pm
PDX
-
MSN
27h 35m2 stops
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$309Delta
Thu, Jan 15 - Sun, Jan 25
United Airlines Logo
11:59 pm - 10:10 am
PDX
-
MSN
8h 11m1 stop
United Airlines Logo
3:48 pm - 10:32 pm
MSN
-
PDX
8h 44m1 stop
$321United Airlines
Fri, Feb 27 - Sun, Mar 1
United Airlines Logo
11:59 pm - 10:16 am
PDX
-
MSN
8h 17m1 stop
United Airlines Logo
2:48 pm - 10:40 pm
MSN
-
PDX
9h 52m1 stop
$328United Airlines
Thu, Jan 22 - Mon, Jan 26
Delta Logo
12:40 am - 10:19 am
PDX
-
MSN
7h 39m1 stop
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$334Delta
Fri, Feb 27 - Sun, Mar 1
Delta Logo
7:35 pm - 9:02 am
PDX
-
MSN
11h 27m2 stops
Delta Logo
2:48 pm - 8:30 pm
MSN
-
PDX
7h 42m1 stop
$348Delta
Fri, Jan 23 - Mon, Jan 26
Delta Logo
5:15 pm - 10:50 pm
PDX
-
MSN
27h 35m2 stops
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$354Delta
Sat, Feb 21 - Tue, Apr 21
United Airlines Logo
5:05 am - 3:02 pm
PDX
-
MSN
7h 57m2 stops
United Airlines Logo
4:03 pm - 10:52 pm
MSN
-
PDX
8h 49m2 stops
$361United Airlines
Fri, Jan 23 - Thu, Jan 29
Delta Logo
7:37 pm - 9:09 am
PDX
-
MSN
11h 32m2 stops
Delta Logo
11:00 am - 5:35 pm
MSN
-
PDX
8h 35m1 stop
$362Delta
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 Sundays 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 $312 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $574 and $571 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 2 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$208
Best time to beat the crowds with an average 32% 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 $208 for a one-way ticket and $289 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, oneworld, and Star Alliance are the airline alliances operating flights between Portland and Madison, with SkyTeam being the most commonly used for this route.

  • 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 $442 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 11429 reviews
7.1Food
8.5Crew
8.1Boarding
7.0Entertainment
7.8Comfort
Airline reviews

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

8.0 ExcellentAnonymous, Dec 2025
PDX - PHX
Read more Alaska Airlines reviews

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

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!!

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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

Information on your arrival and departure airports