$99 Cheap Sun Country Airlines flights Madison (MSN) to Portland (PDX)

View $99 flight on Fri, Oct 24, 2025Opens in a new window

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$99 Cheap Sun Country Airlines flights Madison (MSN) to Portland (PDX)

Prices were available within the past 7 days and start at $99 for one-way flights and $214 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun Country Airlines
Fri, Oct 24 - Sun, Oct 26
MSN
Madison
PDX
Portland
$214 Roundtrip, found 1 hour ago
$214
Roundtrip
found 1 hour ago
Select Sun Country Airlines flight, departing Fri, Oct 24 from Madison to Portland, returning Sun, Oct 26, priced at $214 found 1 hour ago
Flights from Madison (MSN) to Portland (PDX)
Origin airport
Dane County Regional
Destination airport
Portland Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Sun Country Airlines, United
Popular airline
Delta
Distance
1638 mi

Frequently asked questions

How much is a Sun Country Airlines flight from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX)?
Landing cheap one-way Sun Country Airlines flights from MSN to PDX from $99 on Expedia is simple --- just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly return fares from $214 for your next exciting adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from MSN to PDX with Sun Country Airlines?
Sun Country Airlines flights to Portland tend to be more affordable in the quieter months of January and December. Whether you need a one-way or round-trip ticket, you could land a better deal then.
What is the cheapest time to book flights from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX) with Sun Country Airlines?
For cheap Sun Country Airlines fares from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX), start searching one to three months before your intended departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the overall cost. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Sun Country Airlines fly nonstop from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX)?
Click on our "Nonstop" filter when searching for direct Sun Country Airlines flights from MSN to PDX. It's also a great way to compare other airlines servicing the same nonstop route.
What is the earliest Sun Country Airlines flight from MSN to PDX?
To find the earliest departures from MSN to PDX with Sun Country Airlines, filter your results by "Early Morning" and "Morning." Booking an early flight usually means you're less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Sun Country Airlines fly into in Portland?
Sun Country Airlines flights from Dane County Regional Airport (MSN) to Portland arrive at Portland Intl. Airport (PDX). This is the main entry point to this city.
What kind of luggage can I take on a Sun Country Airlines flight from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX)?
On Sun Country Airlines, you can fly standard economy from MSN to PDX with a small personal item and 1 cabin bag. Your carry-on bag should be no larger than 23 inches x 10 inches x 15 inches and weigh less than 33 lb. Exceeding these limits could result in extra charges, so read your carrier's latest guidelines before completing your booking.
Why fly with Sun Country Airlines from MSN to PDX?
Offering a rewarding loyalty program and top-tier customer service, Sun Country Airlines is a top choice for many passengers heading from MSN to PDX. Also, if you're a Sun Country Rewards and One Key™ member booking with Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can be put toward future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Sun Country Airlines flight from Dane County Regional Airport (MSN) to Portland Intl. Airport (PDX)?
Depending on the ticket type you purchased, a fee is typically charged if you cancel or change your flight more than 24 hours after confirmation. To secure flexible fares, select our "Changes included" or "No cancel fee" filter when you look for flights. For more details on changing or canceling your reservation, visit "Trips," select your flight and tick "Manage Booking."

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*Available to One Key members.