$99 Cheap Flights from Portland (PDX) to Madison (MSN)

View $99 flight on Sun, Oct 26, 2025Opens in a new window

Popular airlines from Portland International Airport (PDX) to Dane County Regional Airport (MSN)

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Find available prices by choosing your travel dates.

Cheap Flights from Portland to Madison (PDX-MSN)

Prices were available within the past 7 days and start at $99 for one-way flights and $218 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Apr 26 - Sun, May 4
PDX
Portland
MSN
Madison
$218 Roundtrip, found 11 hours ago
$218
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Apr 26 from Portland to Madison, returning Sun, May 4, priced at $218 found 11 hours ago
Frontier Airlines
Thu, May 29 - Thu, Jun 5
PDX
Portland
MSN
Madison
$228 Roundtrip, found 7 hours ago
$228
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Portland to Madison, returning Thu, Jun 5, priced at $228 found 7 hours ago
United
Sun, May 25 - Thu, May 29
PDX
Portland
MSN
Madison
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select United flight, departing Sun, May 25 from Portland to Madison, returning Thu, May 29, priced at $229 found 1 day ago
Frontier Airlines
Sat, May 24 - Sun, Jun 1
PDX
Portland
MSN
Madison
$238 Roundtrip, found 14 hours ago
$238
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Portland to Madison, returning Sun, Jun 1, priced at $238 found 14 hours ago
Frontier Airlines
Sun, May 25 - Thu, May 29
PDX
Portland
MSN
Madison
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 25 from Portland to Madison, returning Thu, May 29, priced at $244 found 1 day ago
Frontier Airlines
Thu, May 8 - Thu, May 15
PDX
Portland
MSN
Madison
$248 Roundtrip, found 12 hours ago
$248
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Portland to Madison, returning Thu, May 15, priced at $248 found 12 hours ago
American Airlines
Wed, Jun 4 - Sun, Jun 8
PDX
Portland
MSN
Madison
$250 Roundtrip, found 5 days ago
$250
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jun 4 from Portland to Madison, returning Sun, Jun 8, priced at $250 found 5 days ago
Frontier Airlines
Thu, May 15 - Sun, May 18
PDX
Portland
MSN
Madison
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 15 from Portland to Madison, returning Sun, May 18, priced at $250 found 1 day ago
Delta
Tue, Jul 8 - Wed, Jul 16
PDX
Portland
MSN
Madison
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jul 8 from Portland to Madison, returning Wed, Jul 16, priced at $251 found 1 hour ago
Alaska Airlines
Wed, May 28 - Sat, May 31
PDX
Portland
MSN
Madison
$319 Roundtrip, found 14 hours ago
$319
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Wed, May 28 from Portland to Madison, returning Sat, May 31, priced at $319 found 14 hours ago
Flights from Portland (PDX) to Madison (MSN)
Origin airport
Portland Intl.
Destination airport
Dane County Regional
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, United
Roundtrip price
$188
Distance
1638 mi

Portland to Madison Flights

The cheapest times to fly from Portland to Madison

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Madison are during the month of April. You can find some of the cheapest flights from Portland to Madison with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Portland to Madison

Sunday is one of the best days to book for cheap flights from Portland to Madison: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Portland to Madison

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Madison in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Madison flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Madison airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN) cost?
Discover the latest flight deals from PDX to MSN by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PDX to MSN?
The cheapest flights from PDX to MSN are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from PDX to MSN?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from PDX to MSN. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN)?
You’ll have to book a flight with a layover when traveling from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN). Direct flights don’t operate daily on this route. However, just filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from PDX to MSN?
Usually you’ll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN)?
To reach Dane County Regional Airport (MSN) without delays, opt for a flight that leaves from Portland Intl. Airport (PDX) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN) last-minute?
Holding off until just before your trip to book your flight from PDX to MSN often results in higher prices. While you may find some last-minute deals, there’s no guarantee. Keep your travel plans flexible to boost your chances of snagging a bargain.
Is it cheaper to book a PDX to MSN flight and hotel package?
Securing a PDX to MSN flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Pick from our impressive range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portland Intl. Airport (PDX) to Dane County Regional Airport (MSN)?
Generally, it’s possible to reschedule or cancel your PDX to MSN flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline’s policies in your itinerary to see what changes are possible and whether any costs are involved. You’ll also find more details on our Customer Service portal.

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*Available to One Key members.