PDX - MSN

$203 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 8/11. 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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Everything you should know

Cheapest round-trip
$321
Typical prices: $547-$378
American Airlines
Wed 10/14Tue 10/20
PDX - MSN • 1 stop
Cheapest one-way
$203
Typical prices: $204-$317
Delta
Tue 8/11
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 32m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 18% 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

Wed, Oct 14 - Tue, Oct 20
American Airlines Logo
11:58 pm - 9:16 am
PDX
-
MSN
7h 18m
1 stop
American Airlines Logo
4:10 pm - 11:04 pm
MSN
-
PDX
8h 54m
1 stop
$321American Airlines
Thu, Jul 2 - Sat, Jul 11
Delta Logo
12:33 am - 8:12 am
PDX
-
MSN
5h 39m
1 stop
Delta Logo
12:03 pm - 5:35 pm
MSN
-
PDX
7h 32m
1 stop
$326Delta
Tue, Jul 7 - Sat, Jul 11
United Airlines Logo
11:40 pm - 9:47 am
PDX
-
MSN
8h 07m
1 stop
United Airlines Logo
5:00 am - 9:34 am
MSN
-
PDX
6h 34m
1 stop
$335United Airlines
Wed, Jul 22 - Wed, Jul 29
American Airlines Logo
11:15 pm - 7:51 am
PDX
-
MSN
6h 36m
1 stop
American Airlines Logo
2:55 pm - 9:50 pm
MSN
-
PDX
8h 55m
1 stop
$336American Airlines
Fri, Jul 3 - Sat, Jul 11
Delta Logo
12:33 am - 10:12 am
PDX
-
MSN
7h 39m
1 stop
Delta Logo
2:45 pm - 8:15 pm
MSN
-
PDX
7h 30m
1 stop
$340Delta
Wed, Sep 9 - Sun, Sep 13
Delta Logo
11:39 am - 9:57 pm
PDX
-
MSN
8h 18m
1 stop
Delta Logo
5:55 pm - 11:34 pm
MSN
-
PDX
7h 39m
1 stop
$345Delta
Fri, Jul 17 - Mon, Jul 20
United Airlines Logo
10:40 pm - 8:39 am
PDX
-
MSN
7h 59m
1 stop
United Airlines Logo
5:00 am - 9:34 am
MSN
-
PDX
6h 34m
1 stop
$349United Airlines
Thu, Jul 2 - Sat, Jul 11
Delta Logo
12:33 am - 8:12 am
PDX
-
MSN
5h 39m
1 stop
Delta Logo
2:45 pm - 8:15 pm
MSN
-
PDX
7h 30m
1 stop
$350Delta
Wed, Sep 2 - Mon, Sep 7
Delta Logo
12:35 am - 8:16 am
PDX
-
MSN
5h 41m
1 stop
Delta Logo
12:10 pm - 5:34 pm
MSN
-
PDX
7h 24m
1 stop
$359Delta
Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
1:34 pm - 10:53 pm
PDX
-
MSN
7h 19m
1 stop
American Airlines Logo
5:11 pm - 12:55 am
MSN
-
PDX
9h 44m
1 stop
$367American Airlines
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 October.

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 12 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$203
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 20% 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 5 days, the lowest price for a flight from Portland to Madison was $203 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 $491 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 $585 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 12479 reviews
8.1Boarding
7.0Food
7.8Comfort
8.5Crew
7.0Entertainment
Airline reviews

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

6.0 GoodTom, Jun 2026
PDX - ATL
Read more Alaska Airlines reviews

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

The seats are too small/crowded. It is frustrating to be forced to sit with someone who is overweight as they crown the other seat. Nothing against the person…just the airline companies who continue(over decades!)to reduce seat sizes. Americans are fat. Those of us who are not are tired of being compromised by the airline companies who don’t faces that fact and make adjustments. Maybe have “overweight seats”? Maybe give us a discount for being forced into an uncomfortable flight due to others overweightness? Please, make adjustments…be accountable. Thanks!

I flew standby with my two children and completely forgot it was Memorial Day weekend. We tried to fly from PDX to YVR. Unfortunately, after four attempts, we gave up and tried SEA instead after the holiday. The ground crew was very helpful, checking us in and accommodating us when we were finally able to get on a flight. The sad part was that they accidentally loaded one of my suitcases on the Vancouver flight without us during one of our attempts to get on a flight, even though it had a standby tag on it. I filed a report with baggage services, and thankfully, it was returned to PDX the following day. AS was in touch with us and updated us on the process of returning the luggage to the USA.

Internet was great. It was nice to watch a movie. The crew was very nice.

On this flight there wer only 25 people on board. So no one in 5 rows ahead of me and noone in 7 rows behind me. So very chill.

Considering my flight to Portland was in a broken chair that I had paid extra for, this one was great. So yeah, wonderful.

Some food or at least snacks need to be offered on long flights. I thought I had ordered food for my husband and I prior to the flight, but was told during the flight that I had not. Perhaps, if you must charge extra for food, let people order on board. We did get some food, which evidently others had decided they didn’t want onboard, but it wasn’t very good. We did like the adherence to takeoff and landing times, and the quick return of our luggage.

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

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

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

It wa sort of on time; the cab was left with some trash

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

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.

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

Information on your arrival and departure airports