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Madison

$121+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or February, booked 9 days in advance, depart on a Tuesday or Friday and return on a Friday

Cheap 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 December 14, 2025.

This American Airlines deal was found by Cheapflights users on 12/12. 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 12/3110:21 pmPDX - MSN
1 stop9h 47mAmerican Airlines
Mon 1/55:40 pmMSN - PDX
1 stop7h 47mAmerican Airlines
Deal found 12/12$374
This United Airlines deal was found by Cheapflights users on 12/12. 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 12/317:45 pmPDX - MSN
2 stops12h 25mUnited Airlines
Mon 1/55:26 pmMSN - PDX
1 stop7h 14mUnited Airlines
Deal found 12/12$402
This Kiwi.com deal was found by Cheapflights users on 12/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:47 pmPDX - MSN
1 stop23h 28mFrontier
Tue 12/304:34 pmMSN - PDX
2 stops24h 26mFrontier
Deal found 12/12$657
This United Airlines deal was found by Cheapflights users on 12/12. 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.
Mon 12/1511:59 pmPDX - MSN
1 stop8h 15mUnited Airlines
Fri 12/195:26 pmMSN - PDX
1 stop27h 35mUnited Airlines
Deal found 12/12$847
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Thu 12/2511:53 amPDX - MSN
1 stop8h 31mAmerican Airlines
Mon 12/293:15 pmMSN - PDX
1 stop9h 51mAmerican Airlines
Deal found 12/12$854
This United Airlines deal was found by Cheapflights users on 12/14. 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.
Thu 12/2512:54 pmPDX - MSN
1 stop7h 09mUnited Airlines
Mon 12/298:15 amMSN - PDX
1 stop16h 44mUnited Airlines
Deal found 12/14$863
This United Airlines deal was found by Cheapflights users on 12/12. 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.
Sun 12/1411:59 pmPDX - MSN
1 stop8h 15mUnited Airlines
Fri 12/195:26 pmMSN - PDX
1 stop27h 35mUnited Airlines
Deal found 12/12$877
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Tue 12/233:00 pmPDX - MSN
1 stop7h 47mAmerican Airlines
Tue 12/303:15 pmMSN - PDX
1 stop8h 44mAmerican Airlines
Deal found 12/12$885

Find 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 December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$275
(United Airlines)

One-way from

$121
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$574
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.
Search Deals
From Portland to Madison Truax Field
Search Deals
One-way flight from Portland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 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 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 December 14, 2025.
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

Sat 1/10

1:24 pm-9:20 pm

1 stop5h 56m

Madison Truax Field

Sat 1/17

12:32 pm-11:06 pm

2 stops12h 34m

$280

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 1/10

6:00 am-5:11 pm

1 stop9h 11m

Madison Truax Field

Sat 1/17

3:09 pm-10:11 pm

1 stop9h 02m

$300

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 1/21

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Tue 1/27

6:30 am-12:46 pm

1 stop8h 16m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 2/5

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Sun 2/8

6:30 am-12:46 pm

1 stop8h 16m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 1/24

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Tue 1/27

11:00 am-5:35 pm

1 stop8h 35m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 1/10

8:30 am-9:05 pm

2 stops10h 35m

Madison Truax Field

Wed 1/14

4:20 pm-9:12 pm

1 stop6h 52m

$314

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/23

10:47 am-7:07 pm

1 stop6h 20m

Madison Truax Field

Thu 1/29

3:48 pm-12:39 am

2 stops10h 51m

$314

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 2/6

8:30 am-9:05 pm

2 stops10h 35m

Madison Truax Field

Sun 2/8

6:30 am-11:57 am

1 stop7h 27m

$314

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/23

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Tue 1/27

11:00 am-8:59 pm

2 stops11h 59m

$319

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 1/15

11:59 pm-10:43 am

1 stop8h 44m

Madison Truax Field

Mon 1/19

1:16 pm-8:28 pm

1 stop9h 12m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 21 results
1
2
3

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 December.
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 December 12, 2025.

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.

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

Find hourly flight availability from Portland to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 14, 2025.

One of the essential ways to save on airfare from Portland to Madison is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 84% on airfare.

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 December 14, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and United 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.
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,450 reviews
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,007 reviews
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,094 reviews
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Frontier
5.8
Fair
3,081 reviews
Alaska Airlines
8.0
Very good
11,450 reviews

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 5h 56m. 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 67% 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 5 airlines flying from Portland to Madison

Discover the top 5 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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$273Average$445FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$450FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$311Average$472FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$739FlexibilityNo cancel feeOn-time75%

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