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$131+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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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 July 27, 2026.

This CheapOair deal was found by Cheapflights users on 7/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:54 pm
MSN
-
PDX
1 stop22h 41m
Frontier
Fri 10/2312:34 pm
PDX
-
MSN
1 stop28h 13m
Frontier
Deal found 7/23$267
This CheapOair deal was found by Cheapflights users on 7/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:42 pm
MSN
-
PDX
1 stop22h 53m
Frontier
Sun 10/43:22 pm
PDX
-
MSN
1 stop25h 25m
Frontier
Deal found 7/24$271
This CheapOair deal was found by Cheapflights users on 7/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:42 pm
MSN
-
PDX
1 stop22h 53m
Frontier
Tue 10/205:35 pm
PDX
-
MSN
1 stop23h 12m
Frontier
Deal found 7/24$272
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 9/511:29 am
MSN
-
PDX
1 stop8h 01m
American Airlines
Tue 9/157:00 am
PDX
-
MSN
1 stop9h 29m
American Airlines
Deal found 7/22$321
This Delta deal was found by Cheapflights users on 7/23. 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 9/52:51 pm
MSN
-
PDX
1 stop7h 26m
Delta
Tue 9/156:00 am
PDX
-
MSN
1 stop6h 07m
Delta
Deal found 7/23$331
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.
Sat 8/296:30 am
MSN
-
PDX
2 stops8h 44m
United Airlines
Sat 9/510:35 am
PDX
-
MSN
1 stop6h 21m
United Airlines
Deal found 7/27$336
This CheapOair deal was found by Cheapflights users on 7/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:55 pm
MSN
-
PDX
1 stop22h 56m
Frontier
Sat 8/2212:20 pm
PDX
-
MSN
1 stop28h 50m
Frontier
Deal found 7/26$342
This Delta deal was found by Cheapflights users on 7/22. 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.
Wed 9/26:16 pm
MSN
-
PDX
1 stop7h 04m
Delta
Wed 9/912:25 am
PDX
-
MSN
1 stop5h 57m
Delta
Deal found 7/22$345
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 8/216:53 pm
MSN
-
PDX
1 stop7h 06m
American Airlines
Fri 8/2811:34 pm
PDX
-
MSN
1 stop7h 52m
American Airlines
Deal found 7/22$349
This United Airlines deal was found by Cheapflights users on 7/23. 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 8/213:55 pm
MSN
-
PDX
2 stops8h 59m
United Airlines
Tue 8/255:00 am
PDX
-
MSN
1 stop6h 13m
United Airlines
Deal found 7/23$350

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$267
(CheapOair)

One-way from

$131
(CheapOair)

Popular in

March

Cheapest in

February

Average price

$491
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. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 27, 2026.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 10/16

7:53 pm-11:43 pm

1 stop5h 50m

Portland

Sat 10/24

11:30 am-9:02 pm

1 stop7h 32m

$345

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 9/2

8:10 am-3:05 pm

2 stops8h 55m

Portland

Sun 9/6

5:00 am-1:13 pm

1 stop6h 13m

$350
Quickest round-trip

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sun 8/9

6:05 am-10:41 am

1 stop6h 36m

Portland

Fri 8/21

12:35 am-8:16 am

1 stop5h 41m

$394

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 8/15

5:00 am-12:00 pm

2 stops9h 00m

Portland

Fri 8/21

4:07 pm-11:59 pm

1 stop5h 52m

$395

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 9/15

4:06 pm-10:52 pm

1 stop8h 46m

Portland

Sat 9/26

7:02 am-3:04 pm

1 stop6h 02m

$431

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 9/19

6:30 am-11:28 am

1 stop6h 58m

Portland

Wed 9/23

8:40 am-8:53 pm

2 stops10h 13m

$436

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 9/22

5:00 am-2:46 pm

2 stops11h 46m

Portland

Tue 9/29

10:43 am-10:35 pm

2 stops9h 52m

$441

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 8/21

3:55 pm-10:54 pm

2 stops8h 59m

Portland

Fri 8/28

4:07 pm-11:59 pm

1 stop5h 52m

$464

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Mon 8/31

5:00 am-9:32 am

1 stop6h 32m

Portland

Sun 9/6

7:00 am-8:39 pm

2 stops11h 39m

$464
Cheapest one-way

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 9/12

10:46 am-8:39 pm

2 stops11h 53m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 20 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Portland flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 31 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, February is the cheapest month in which you can book a flight from Madison to Portland (average of $360). Flying from Madison to Portland in March is currently the most expensive (average of $543). 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.

How much does it cost to fly round-trip from Madison to Portland?

Airfare is below average for this route at the moment.

Madison to Portland flights typically cost between $348 and $550 in October.
The cheapest round-trip price found within the last 5 days was $267 on Frontier (Oct 17-Oct 23).

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 27, 2026.
Read through reviews of airlines operating flights from Madison to Portland, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,482 reviews

Boarding

8.1

Comfort

7.8

Overall

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,482 reviews
Delta
7.8
Good
8,482 reviews

Boarding

8.1

Comfort

7.8

Overall

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,041 reviews
Delta
7.8
Good
8,482 reviews

Boarding

8.1

Comfort

7.8

Overall

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,836 reviews
Delta
7.8
Good
8,482 reviews

Boarding

8.1

Comfort

7.8

Overall

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 5h 50m. Fly via Delta or United Airlines 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 $288, American Airlines will fly you from Madison to Portland and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Delta - these airlines can fly you to your destination from $288 and $288, respectively. These flights start at 35% 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 $115. United Airlines flights start at $198 while deals on American Airlines start at $208 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, February is the cheapest month in which you can book a flight from Madison to Portland (average of $360). Flying from Madison to Portland in March is currently the most expensive (average of $543). 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
Beaverton
Seaside
Lincoln City
Vancouver
Longview
Lake Oswego
Hillsboro
Kelso
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Madison to Portland

Discover the top 3 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$288Average$450FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$288Average$440FlexibilityNo cancel feeOn-timeN/A

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