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$223+ Cheap flights from Madison to Portland (MSN - PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in September or October, booked 85 days in advance, depart on a Friday or Tuesday and return on a Tuesday

Cheap flight deals from Madison to Portland

Cheapest flights from Madison to Portland
Explore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/163:59 pmMSN - PDX
1 stop8h 16mUnited Airlines
Mon 12/225:00 amPDX - MSN
1 stop7h 04mUnited Airlines
Deal found 12/9$466
This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:00 amMSN - PDX
1 stop8h 58mUnited Airlines
Thu 1/15:00 amPDX - MSN
1 stop7h 04mUnited Airlines
Deal found 12/10$494
This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:29 pmMSN - PDX
2 stops10h 30mUnited Airlines
Mon 12/2911:55 pmPDX - MSN
1 stop8h 15mUnited Airlines
Deal found 12/10$499
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/133:00 pmMSN - PDX
1 stop7h 52mDelta
Wed 12/1711:54 amPDX - MSN
1 stop8h 32mDelta
Deal found 12/10$502
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1311:04 amMSN - PDX
1 stop8h 39mDelta
Mon 12/1512:32 amPDX - MSN
1 stop7h 43mDelta
Deal found 12/10$505
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:44 amMSN - PDX
1 stop9h 51mDelta
Wed 12/1711:54 amPDX - MSN
1 stop8h 32mDelta
Deal found 12/10$509
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:44 amMSN - PDX
1 stop9h 51mDelta
Tue 12/1611:25 pmPDX - MSN
1 stop7h 35mDelta
Deal found 12/10$512
This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:59 pmMSN - PDX
1 stop8h 16mUnited Airlines
Sun 12/145:00 amPDX - MSN
1 stop7h 06mUnited Airlines
Deal found 12/10$519
This United Airlines deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:48 pmMSN - PDX
2 stops11h 49mUnited Airlines
Sun 12/147:00 amPDX - MSN
1 stop5h 54mUnited Airlines
Deal found 12/9$524

Find flight deals from Madison to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(United Airlines)

One-way from

$223
(Delta)

Popular in

June

Cheapest in

September

Average price

$465
Provider with most accurate pricing for Madison Truax Field-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Portland flights.
Search Deals
From Madison Truax Field to Portland
Search Deals
One-way flight from Madison Truax Field to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Madison

Fly to

Portland

Route

Depart

Return

Price

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 1/7

4:20 pm-9:12 pm

1 stop6h 52m

Portland

Wed 1/14

7:00 am-2:52 pm

1 stop5h 52m

$289

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 5/13

6:15 am-12:54 pm

1 stop8h 39m

Portland

Sat 5/16

11:39 am-9:57 pm

1 stop8h 18m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 1/23

6:30 am-11:57 am

1 stop7h 27m

Portland

Mon 1/26

11:59 pm-10:10 am

1 stop8h 11m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 5/13

9:45 am-5:38 pm

2 stops9h 53m

Portland

Sat 5/16

12:40 pm-8:45 pm

1 stop6h 05m

$328

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 2/13

6:00 am-10:49 am

1 stop6h 49m

Portland

Sun 2/15

11:59 pm-10:38 am

1 stop8h 39m

$329

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 4/17

6:49 pm-11:37 pm

1 stop6h 48m

Portland

Wed 4/22

11:59 pm-10:31 am

1 stop8h 32m

$329

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 1/10

11:00 am-6:50 pm

2 stops9h 50m

Portland

Sat 1/31

1:30 pm-10:50 pm

2 stops7h 20m

$330

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 1/17

6:30 am-6:56 pm

2 stops14h 26m

Portland

Wed 1/21

1:24 pm-9:20 pm

1 stop5h 56m

$360

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Mon 3/2

1:23 pm-8:55 pm

2 stops9h 32m

$223

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 5/20

3:33 pm-8:54 pm

1 stop7h 21m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 17 results
1
2

Compare providers for flights from Madison to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Portland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Portland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Madison-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Portland flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Madison to Portland?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Portland. Price data was last updated on December 5, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 85 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Madison to Portland?

Currently, September is the cheapest month in which you can book a flight from Madison to Portland (average of $128). Flying from Madison to Portland in January is currently the most expensive (average of $288). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to PDX?

Find hourly flight availability from Madison to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

One of the essential ways to save on airfare from Madison to Portland is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 46% on airfare.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 12, 2025.
Read through reviews of airlines operating flights from Madison to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,084 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Madison to Portland?

    There are many flights that can get you from Madison to Portland in 6h 52m. Fly via United Airlines or Delta to get the fastest option. Madison and Portland are separated by a distance of 1639 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Madison to Portland round-trip?

    Currently priced at $214, Frontier will fly you from Madison to Portland and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $269 and $288, respectively. These flights start at 50% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Madison to Portland one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $97. American Airlines flights start at $114 while deals on Delta start at $189 one-way.

  • Can I find deals for flights from Madison to Portland that include hotel bookings?

    Yes. In addition to deals on Madison to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Portland.

  • Can I find deals for business class flights from Madison to Portland?

    Yes. Cheapflights offers flight deals from Madison to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Portland?

    Currently, September is the cheapest month in which you can book a flight from Madison to Portland (average of $128). Flying from Madison to Portland in January is currently the most expensive (average of $288). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Lake Oswego
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham

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Top 4 airlines flying from Madison to Portland

Discover the top 4 airlines that operate flights from Madison to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$214Average$300FlexibilityNo cancel feeOn-time62%
DeltaCheapest$282Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$288Average$457FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$420FlexibilityNo cancel feeOn-time71%

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