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$109+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in September or November, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap 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 July 29, 2025.

Round-trip from

$238
(Frontier)

One-way from

$109
(Frontier)

Popular in

December

Cheapest in

September

Average price

$461
From Madison Truax Field to Portland
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One-way flight from Madison Truax Field to Portland
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 29, 2025.

This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:18 pmMSN - PDX
1 stop6h 06mFrontier
Fri 10/36:05 amPDX - MSN
1 stop11h 09mFrontier
Deal found 7/28$238
This Delta deal was found by Cheapflights users on 7/29. 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 10/2411:40 amMSN - PDX
Nonstop4h 06mDelta
Sun 10/261:10 pmPDX - MSN
Nonstop3h 34mDelta
Deal found 7/29$269
This United Airlines deal was found by Cheapflights users on 7/27. 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 9/164:30 pmMSN - PDX
2 stops10h 15mUnited Airlines
Sat 9/2010:51 amPDX - MSN
1 stop6h 18mUnited Airlines
Deal found 7/27$294
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/133:55 pmMSN - PDX
1 stop9h 25mAmerican Airlines
Sat 10/45:38 amPDX - MSN
1 stop9h 14mAmerican Airlines
Deal found 7/27$314

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 July 29, 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

Tue 8/12

7:18 pm-11:24 pm

1 stop6h 06m

Portland

Fri 10/3

6:05 am-7:14 pm

1 stop11h 09m

$238

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 10/24

11:40 am-1:46 pm

Nonstop4h 06m

Portland

Sun 10/26

1:10 pm-6:44 pm

Nonstop3h 34m

$269

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 9/16

4:30 pm-12:45 am

2 stops10h 15m

Portland

Sat 9/20

10:51 am-7:09 pm

1 stop6h 18m

$294

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 8/13

3:55 pm-11:20 pm

1 stop9h 25m

Portland

Sat 10/4

5:38 am-4:52 pm

1 stop9h 14m

$314

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 8/12

7:18 pm-11:24 pm

1 stop6h 06m

$109

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 8/26

6:05 am-12:41 pm

1 stop8h 36m

$190

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 8/27

8:15 am-8:03 pm

2 stops13h 48m

$240

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sun 8/10

5:36 pm-11:07 pm

1 stop7h 31m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 8/9

8:46 am-9:18 am

2 stops26h 32m

$337

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Mon 10/27

2:45 pm-11:37 pm

2 stops10h 52m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 42 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, November is the cheapest month in which you can book a flight from Madison to Portland (average of $277). Flying from Madison to Portland in March is currently the most expensive (average of $368). 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 July 29, 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 at noon could potentially save you up to 56% 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 July 29, 2025.
Read through reviews of airlines operating flights from Madison to Portland, such as Alaska Airlines, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Frontier
5.9
Fair
3,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Currently priced at $238, 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 United Airlines - these airlines can fly you to your destination from $269 and $294, respectively. These flights start at 45% 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 $109. Delta flights start at $190 while deals on United Airlines start at $240 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, November is the cheapest month in which you can book a flight from Madison to Portland (average of $277). Flying from Madison to Portland in March is currently the most expensive (average of $368). 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
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Astoria
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Woodburn
Stevenson
Wilsonville
Pacific City
Troutdale
Tillamook

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$226FlexibilityNo cancel feeOn-time62%
DeltaCheapest$283Average$420FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$422FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$465FlexibilityNo cancel feeOn-time69%

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