PDX - MSN

$86 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 11/16. 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, Sep 5 - Sun, Sep 7
Frontier Logo
6:05 am - 7:14 pmPDX-MSN
11h 09m1 stop
Frontier Logo
7:59 pm - 12:12 amMSN-PDX
6h 13m1 stop
$224Frontier
Find Deal
Thu, Sep 4 - Mon, Sep 8
Frontier Logo
6:05 am - 7:14 pmPDX-MSN
11h 09m1 stop
Frontier Logo
7:59 pm - 12:12 amMSN-PDX
6h 13m1 stop
$258Frontier
Find Deal
Thu, Sep 11 - Thu, Sep 18
Frontier Logo
6:05 am - 7:14 pmPDX-MSN
11h 09m1 stop
Frontier Logo
7:59 pm - 12:12 amMSN-PDX
6h 13m1 stop
$263Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
6:05 am - 7:14 pmPDX-MSN
11h 09m1 stop
Frontier Logo
7:59 pm - 12:12 amMSN-PDX
6h 13m1 stop
$288Frontier
Find Deal
Fri, Oct 3 - Sat, Oct 18
Delta Logo
10:50 pm - 8:47 amPDX-MSN
7h 57m1 stop
Delta Logo
10:58 am - 5:27 pmMSN-PDX
8h 29m1 stop
$289Delta
Find Deal
Sat, Sep 6 - Tue, Sep 16
Delta Logo
10:05 pm - 9:56 amPDX-MSN
9h 51m1 stop
Delta Logo
5:26 pm - 8:56 pmMSN-PDX
5h 30m1 stop
$314Delta
Find Deal
Wed, Sep 10 - Tue, Sep 16
United Airlines Logo
10:55 am - 10:23 pmPDX-MSN
9h 28m2 stops
United Airlines Logo
4:30 pm - 9:01 pmMSN-PDX
6h 31m1 stop
$351United Airlines
Find Deal
Fri, Sep 12 - Mon, Sep 22
American Airlines Logo
11:18 am - 7:54 pmPDX-MSN
6h 36m1 stop
American Airlines Logo
5:00 am - 9:37 amMSN-PDX
6h 37m1 stop
$354American Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
United Airlines Logo
8:30 am - 4:44 pmPDX-MSN
6h 14m1 stop
United Airlines Logo
6:30 am - 1:03 pmMSN-PDX
8h 33m2 stops
$359United Airlines
Find Deal
Wed, Oct 8 - Sun, Oct 12
American Airlines Logo
5:05 am - 2:00 pmPDX-MSN
6h 55m1 stop
American Airlines Logo
8:25 pm - 9:31 amMSN-PDX
15h 06m1 stop
$387American Airlines
Find Deal
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 $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 15% 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$86
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 26% 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 $86 for a one-way ticket and $224 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 oneworld 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 $668 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 $451 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.

Prefer to fly direct from Portland to Madison?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Portland to Madison Truax Field.
Find which airlines fly direct from Portland Airport to Madison Truax Field Airport, which days they fly and book direct flights.

Direct departures

Portland to Madison Truax Field

Sunday

Delta

Delta

See more direct flights

Direct returns

Madison Truax Field to Portland

Friday

Delta

Delta

See more direct flights

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 10000 reviews
8.5Crew
7.8Comfort
7.0Entertainment
7.1Food
8.1Boarding
Airline reviews

Everything except for the lack of a choice of the snack provided was great.

10.0 ExcellentAnonymous, Aug 2025PDX - OAK
Read more Alaska Airlines reviews

Everything except for the lack of a choice of the snack provided was great.

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

First time flying with Alaska, and it went great. Thank you for a great experience flying to PDX.

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

We did not realize there wasn't any food apart from a small packet of pretzels - I dropped one and nearly cried.

I recently flew with Alaska Airlines on a trip to Oregon and had a very frustrating experience that I hope the airline can learn from. I purchased upgraded seats with extra legroom for my flight, paying the additional fees for the comfort and space. During my trip planning, I called customer service to inquire about their pet travel policies and conditions, as I was considering bringing my dogs. However, I ultimately decided NOT to bring my pets and never authorized or confirmed any pet travel arrangements. Despite this, Alaska Airlines took it upon themselves to change my seat assignment without any notification or contact. When I arrived for my flight, I discovered that my paid upgrade had been downgraded to a regular seat - presumably because they assumed I would be traveling with pets based on my inquiry call. I hope Alaska Airlines will improve their communication processes and ensure that customer inquiries don’t automatically trigger booking changes without explicit customer authorization. Better staff training on distinguishing between inquiries and actual bookings would prevent this type of situation in the future. While I appreciate that the airline tries to accommodate pet travelers, making assumptions and changes without customer consent is poor service that needs to be addressed.

The customer service personnel were excellent. We had pre-ordered two meals but they could only provide one of them; they substituted the meal with a snack at no charge. Flight was on-time.

At the Portland airport, Alaska Airlines has put in a system where you have to create your own bag tag, then put your own suitcase onto a scale to weigh it. The day we were there, the system was not working properly, and we kept on being told to go onto different lines so it took us approximately 45 minutes to check our bag in. I do not work for the airlines why am I subjected to doing this? How all these companies are shifting their work onto people who have paid good money for their products is crazy. And then the system that the customers are supposed to use don't work properly..

Flight was great. Baggage claim at both ends (SEA and ATL) was atrocious.

Had to sit and wait to get off the plane for closeto a hour. My son also flying to a different destination that day also had like a 2.5 hr delay

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

The flight was comfortable with the exit row and great service

Had to cancel first flight because Airporter Bus took over 3 hrs to get to airport which resulted in an extra $378 dollar fare . Is there anyway I can be reimbursed for initial fare since it was not my fault? Sent from my iPhone EJ Ledet

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

This flight was perfect. No complaints and only the highest regard for the crew and ground staff and how they executed perfectly. I fly a lot with United and would request predictability and transparency in their operations instead of last minute changes.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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