PDX - MSN

$209 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 5/27. 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
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$321
Typical prices: $604-$399
United Airlines
Thu 5/28Wed 6/3
PDX - MSN • 1 stop
Cheapest one-way
$209
Typical prices: $216-$298
United Airlines
Wed 5/27
PDX - MSN • 1 stop
Top airlines
Cheapest • from $321 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Madison. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $288 (round-trip)
Shortest trip • 6h 30m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 8 weeks in advance save around 20% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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, May 28 - Wed, Jun 3
United Airlines Logo
10:40 pm - 8:06 am
PDX
-
MSN
7h 26m
1 stop
United Airlines Logo
6:30 am - 11:38 am
MSN
-
PDX
7h 08m
1 stop
$321United Airlines
Fri, Jul 3 - Sat, Jul 11
United Airlines Logo
10:40 pm - 8:55 am
PDX
-
MSN
8h 15m
1 stop
United Airlines Logo
5:00 am - 9:34 am
MSN
-
PDX
6h 34m
1 stop
$335United Airlines
Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
10:57 pm - 7:51 am
PDX
-
MSN
6h 54m
1 stop
American Airlines Logo
5:00 am - 10:36 am
MSN
-
PDX
7h 36m
1 stop
$345American Airlines
Tue, May 26 - Sun, May 31
American Airlines Logo
11:43 pm - 10:38 am
PDX
-
MSN
8h 55m
1 stop
American Airlines Logo
6:44 pm - 11:52 pm
MSN
-
PDX
7h 08m
1 stop
$349American Airlines
Thu, May 28 - Tue, Jun 2
United Airlines Logo
4:15 pm - 11:59 pm
PDX
-
MSN
5h 44m
1 stop
United Airlines Logo
10:40 am - 5:46 pm
MSN
-
PDX
9h 06m
2 stops
$363United Airlines
Thu, Jul 16 - Mon, Jul 20
Delta Logo
12:33 am - 8:11 am
PDX
-
MSN
5h 38m
1 stop
Delta Logo
6:00 am - 10:41 am
MSN
-
PDX
6h 41m
1 stop
$369Delta
Sat, Jun 20 - Wed, Jun 24
United Airlines Logo
10:40 pm - 8:55 am
PDX
-
MSN
8h 15m
1 stop
United Airlines Logo
5:00 am - 9:39 am
MSN
-
PDX
6h 39m
1 stop
$373United Airlines
Fri, Jul 3 - Sat, Jul 11
Delta Logo
12:33 am - 10:12 am
PDX
-
MSN
7h 39m
1 stop
Delta Logo
6:00 am - 10:42 am
MSN
-
PDX
6h 42m
1 stop
$380Delta
Sat, Jul 18 - Wed, Jul 22
American Airlines Logo
10:57 pm - 7:51 am
PDX
-
MSN
6h 54m
1 stop
American Airlines Logo
5:11 pm - 10:51 pm
MSN
-
PDX
7h 40m
1 stop
$381American Airlines
Fri, May 15 - Sun, May 24
Delta Logo
9:39 pm - 10:16 am
PDX
-
MSN
10h 37m
1 stop
Delta Logo
11:48 am - 5:15 pm
MSN
-
PDX
7h 27m
1 stop
$384Delta
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.

How much is a round-trip flight from Portland to Madison?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Madison departing in May.

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 February, where tickets cost $398 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $585 and $581 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 8 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$209
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 18% 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 $209 for a one-way ticket and $321 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 aircraft models fly most regularly from Portland to Madison?

    We unfortunately don’t have that data for this specific 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, Delta or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Madison are Delta and Alaska Airlines. With an average price for the route of $489 and an overall rating of 7.9, Delta is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $630 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.

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.
7.9
Alaska AirlinesOverall score based on 12319 reviews
7.8Comfort
7.0Entertainment
8.5Crew
8.1Boarding
7.1Food
Airline reviews

very nice blankets and comfortable seats. great service. Great flights.

10.0 ExcellentAnonymous, Apr 2026
PDX - SEA
Read more Alaska Airlines reviews

very nice blankets and comfortable seats. great service. Great flights.

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

I like not much people. Could tell the kids to be quiet.

I liked everything except, I left a brand new Switch 2 on the plane and talking to anybody about it is nearly impossible. I had to fill out a form and hope they get back to me in the next 2 weeks. I really hope they contact me. I saved for that thing for over a year and my son is heart broken.

Fight attendant excellent Food very good, not great Seats were stiff and uncomfortable Flight was overall very nice. Last three flights were burdened with miserably uncomfortable seats. Hard stiff no padding.

The ground crew was very good. They communicated clearly and continued updating. The flight crew was fine. The flight crew on the March 20th flight from MCI to Portland was excellent.

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.

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

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

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 Portland to Madison

Information on your arrival and departure airports