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$208+ Cheap flights from Portland to Madison (PDX - MSN)

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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Portland to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Madison (MSN). 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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$309
(Delta)

One-way from

$208
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$338
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Madison Truax Field flights.
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From Portland to Madison Truax Field
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One-way flight from Portland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Portland to Madison

Cheapest flights from Portland to Madison
Explore the most affordable flight options available from Portland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This United Airlines deal was found by Cheapflights users on 1/13. 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 8/711:55 pm
PDX
-
MSN
1 stop7h 58m
United Airlines
Tue 8/115:50 pm
MSN
-
PDX
1 stop6h 48m
United Airlines
Deal found 1/13$305
This Delta deal was found by Cheapflights users on 1/14. 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 2/412:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Fri 3/610:59 am
MSN
-
PDX
1 stop8h 34m
Delta
Deal found 1/14$309
This United Airlines deal was found by Cheapflights users on 1/15. 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 2/287:00 am
PDX
-
MSN
1 stop5h 57m
United Airlines
Wed 3/43:53 pm
MSN
-
PDX
2 stops10h 41m
United Airlines
Deal found 1/15$328
This American Airlines deal was found by Cheapflights users on 1/13. 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 2/1311:35 pm
PDX
-
MSN
1 stop7h 42m
American Airlines
Tue 2/176:00 am
MSN
-
PDX
1 stop6h 58m
American Airlines
Deal found 1/13$329
This Delta deal was found by Cheapflights users on 1/14. 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.
Mon 2/212:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Mon 3/92:45 pm
MSN
-
PDX
1 stop8h 27m
Delta
Deal found 1/14$334
This United Airlines deal was found by Cheapflights users on 1/13. 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 1/301:24 pm
PDX
-
MSN
1 stop5h 56m
United Airlines
Tue 2/32:56 pm
MSN
-
PDX
2 stops11h 35m
United Airlines
Deal found 1/13$339
This United Airlines deal was found by Cheapflights users on 1/14. 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 2/1311:59 pm
PDX
-
MSN
1 stop8h 15m
United Airlines
Tue 2/172:48 pm
MSN
-
PDX
2 stops11h 46m
United Airlines
Deal found 1/14$353
This Delta deal was found by Cheapflights users on 1/13. 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.
Tue 1/2711:59 am
PDX
-
MSN
1 stop8h 31m
Delta
Thu 2/511:00 am
MSN
-
PDX
1 stop8h 35m
Delta
Deal found 1/13$354
This United Airlines deal was found by Cheapflights users on 1/13. 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.
Wed 1/281:24 pm
PDX
-
MSN
1 stop5h 56m
United Airlines
Sun 2/16:30 am
MSN
-
PDX
1 stop7h 27m
United Airlines
Deal found 1/13$359
This United Airlines deal was found by Cheapflights users on 1/15. 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.
Wed 6/2411:55 pm
PDX
-
MSN
1 stop7h 58m
United Airlines
Wed 7/16:45 am
MSN
-
PDX
1 stop6h 50m
United Airlines
Deal found 1/15$362
This Delta deal was found by Cheapflights users on 1/14. 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.
Sun 2/81:53 pm
PDX
-
MSN
1 stop6h 57m
Delta
Mon 3/92:45 pm
MSN
-
PDX
1 stop8h 27m
Delta
Deal found 1/14$364
This United Airlines deal was found by Cheapflights users on 1/13. 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 2/215:05 am
PDX
-
MSN
2 stops7h 52m
United Airlines
Sat 2/283:53 pm
MSN
-
PDX
1 stop9h 03m
United Airlines
Deal found 1/13$365

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Madison 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 January 15, 2026.
Use the filters below to find and compare flights from Portland to Madison that are best for you.

Fly from

Portland

Fly to

Madison

Route

Depart

Return

Price

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 2/4

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Wed 3/4

2:51 pm-8:30 pm

1 stop7h 39m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 2/21

11:59 pm-10:14 am

1 stop8h 15m

Madison Truax Field

Sat 2/28

6:30 am-11:55 am

1 stop7h 25m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 2/5

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Tue 3/10

6:00 am-12:48 pm

1 stop8h 48m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 2/6

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Mon 3/9

2:45 pm-9:12 pm

1 stop8h 27m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/30

11:59 pm-10:10 am

1 stop8h 11m

Madison Truax Field

Tue 2/3

12:38 pm-6:56 pm

1 stop8h 18m

$334

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 2/10

6:00 am-4:52 pm

1 stop8h 52m

Madison Truax Field

Mon 2/16

5:00 am-10:58 am

1 stop7h 58m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 1/29

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Fri 2/6

11:00 am-5:35 pm

1 stop8h 35m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/30

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Fri 2/6

11:00 am-5:35 pm

1 stop8h 35m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 1/26

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Wed 2/4

11:00 am-5:35 pm

1 stop8h 35m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 1/27

6:50 am-4:17 pm

1 stop7h 27m

Madison Truax Field

Fri 2/6

6:30 am-12:46 pm

1 stop8h 16m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 19 results
1
2

Compare providers for flights from Portland to Madison

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 Portland to Madison in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 Portland-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Madison 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 Portland-Madison 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 Portland to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Portland 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 Portland to Madison

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

Use this chart to determine the optimal time to book a round-trip flight from Portland to Madison. Price data was last updated on January 9, 2026.

The price you pay for your flight from Portland to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 9 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, October is the cheapest month in which you can book a flight from Portland to Madison (average of $79). Flying from Portland to Madison in March is currently the most expensive (average of $326). 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.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated January 15, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Portland to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,052 reviews

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

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
8,052 reviews
Delta
7.9
Good
8,052 reviews

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

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
9,164 reviews
Delta
7.9
Good
8,052 reviews

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

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
11,136 reviews
Delta
7.9
Good
8,052 reviews

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

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
5.7
Fair
3,057 reviews
Delta
7.9
Good
8,052 reviews

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.8

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 Portland to Madison. 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 Portland to Madison?

    Departing from Portland to Madison will take you 6h 57m. The distance between Portland and Madison is about 1639 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Cheapflights users have booked flights from Portland to Madison round-trip from $149. Other airlines that can offer you cheap pricing are Delta, from $258, and American Airlines, from $283. These flights start at 66% lower than the current average price 3 months from now.

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

    One-way options have recently been found by users for as low as $114 on American Airlines. Other airlines that offer cheap prices include Delta from $114 and Frontier from $139 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Madison 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 Portland to Madison?

    Currently, October is the cheapest month in which you can book a flight from Portland to Madison (average of $79). Flying from Portland to Madison in March is currently the most expensive (average of $326). 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Alternative routes for Portland to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Madison

Discover the top 4 airlines that operate flights from Portland to Madison. 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$258Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$453FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$308Average$466FlexibilityNo cancel feeOn-time69%

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