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$103+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 89 days in advance, depart on a Tuesday or Saturday and return on a Friday

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(Delta)

One-way from

$103
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$443

Good round-trip deal

$793 or less
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
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Highest demand for flights based on searches. 8% potential increase in price ($41 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 October 2025
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Price to beat on a round-trip flight from Portland to Madison Truax Field.
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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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/1011:20 pmPDX - MSN
1 stop7h 40mDelta
Sun 12/146:00 amMSN - PDX
1 stop8h 54mDelta
Deal found 10/29$289
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:59 pmPDX - MSN
1 stop6h 58mDelta
Sat 12/66:00 amMSN - PDX
2 stops18h 37mDelta
Deal found 10/28$300
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:26 pmPDX - MSN
2 stops26h 02mMultiple Airlines
Sat 11/223:04 pmMSN - PDX
1 stop26h 03mMultiple Airlines
Deal found 10/28$321
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2112:47 pmPDX - MSN
2 stops22h 29mMultiple Airlines
Wed 12/313:00 pmMSN - PDX
1 stop22h 43mMultiple Airlines
Deal found 10/27$333
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/1210:15 pmPDX - MSN
1 stop10h 25mAmerican Airlines
Sun 11/165:00 amMSN - PDX
1 stop9h 36mAmerican Airlines
Deal found 10/27$339
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2112:47 pmPDX - MSN
1 stop23h 14mFrontier
Wed 12/313:00 pmMSN - PDX
1 stop22h 43mFrontier
Deal found 10/27$343
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2112:47 pmPDX - MSN
2 stops22h 29mMultiple Airlines
Fri 1/22:53 pmMSN - PDX
1 stop22h 59mMultiple Airlines
Deal found 10/27$347
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:32 amPDX - MSN
1 stop7h 43mDelta
Mon 12/156:00 amMSN - PDX
1 stop8h 54mDelta
Deal found 10/28$353

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 October 29, 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

Tue 12/9

12:32 am-10:15 am

1 stop7h 43m

Madison Truax Field

Sun 12/14

10:55 am-5:43 pm

1 stop8h 48m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 4/14

12:55 am-10:00 am

1 stop7h 05m

Madison Truax Field

Sat 4/18

10:55 am-4:36 pm

1 stop7h 41m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 12/2

12:32 am-10:15 am

1 stop7h 43m

Madison Truax Field

Sat 12/6

6:00 am-10:37 pm

2 stops18h 37m

$300

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 12/10

7:30 pm-9:00 am

2 stops11h 30m

Madison Truax Field

Mon 12/15

1:35 pm-10:40 pm

2 stops11h 05m

$329

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 11/25

2:31 pm-3:29 pm

1 stop22h 58m

$154

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 11/22

2:30 pm-11:40 am

1 stop19h 10m

$155

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 12/25

12:47 pm-2:00 pm

3 stops23h 13m

$174

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 12/17

7:30 pm-10:15 am

2 stops12h 45m

$175

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 12/28

12:47 pm-2:01 pm

1 stop23h 14m

$176

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 11/22

2:23 pm-10:11 am

2 stops17h 48m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 14 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 October.
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 October 24, 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 29 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, August is the cheapest month in which you can book a flight from Portland to Madison (average of $82). 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 October 29, 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 72% 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 October 29, 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
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,212 reviews
Alaska Airlines
8.0
Very good
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,992 reviews
Alaska Airlines
8.0
Very good
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,999 reviews
Alaska Airlines
8.0
Very good
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,030 reviews
Alaska Airlines
8.0
Very good
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Frontier
5.8
Fair
3,124 reviews
Alaska Airlines
8.0
Very good
11,212 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 7h 43m. The distance between Portland and Madison is about 1639 mi.

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

    Cheapflights users have booked flights from Portland to Madison round-trip from $148. Other airlines that can offer you cheap pricing are Delta, from $273, and American Airlines, from $283. These flights start at 67% lower than the current average price 3 months from now.

  • What are the cheapest flights from Portland to Madison?

    The cheapest flight price from Portland to Madison is $775. On average you can expect to pay $793. The most popular route, (Portland - Madison Truax Field), can usually be booked for $289.

  • 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, August is the cheapest month in which you can book a flight from Portland to Madison (average of $82). 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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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$273Average$455FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$418FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$319Average$489FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$739FlexibilityNo cancel feeOn-time75%

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