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$129+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or August, booked 27 days in advance, depart on a Tuesday or Saturday and return on a Tuesday

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 July 29, 2025.

Round-trip from

$218
(Frontier)

One-way from

$129
(Frontier)

Popular in

July

Cheapest in

January

Average price

$575

Good round-trip deal

$793 or less

Good one-way deal

$99 or less
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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Portland to Madison Truax Field.
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Price to beat on a one-way 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 July 29, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:35 amPDX - MSN
1 stop9h 58mFrontier
Tue 8/127:18 pmMSN - PDX
1 stop6h 06mFrontier
Deal found 7/29$218
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.
Sat 9/610:57 pmPDX - MSN
1 stop7h 51mDelta
Sat 9/132:44 pmMSN - PDX
1 stop8h 12mDelta
Deal found 7/29$289
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/412:59 amPDX - MSN
1 stop7h 47mAmerican Airlines
Tue 8/126:44 pmMSN - PDX
1 stop6h 36mAmerican Airlines
Deal found 7/29$379
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/610:55 amPDX - MSN
1 stop7h 53mUnited Airlines
Sat 9/1310:51 amMSN - PDX
2 stops12h 10mUnited Airlines
Deal found 7/28$384

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 July 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 8/5

6:35 am-6:33 pm

1 stop9h 58m

Madison Truax Field

Tue 8/12

7:18 pm-11:24 pm

1 stop6h 06m

$218

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 9/6

10:57 pm-8:48 am

1 stop7h 51m

Madison Truax Field

Sat 9/13

2:44 pm-8:56 pm

1 stop8h 12m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 8/4

12:59 am-10:46 am

1 stop7h 47m

Madison Truax Field

Tue 8/12

6:44 pm-11:20 pm

1 stop6h 36m

$379

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 9/6

10:55 am-8:48 pm

1 stop7h 53m

Madison Truax Field

Sat 9/13

10:51 am-9:01 pm

2 stops12h 10m

$384

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 10/27

8:57 am-6:56 pm

1 stop7h 59m

$129

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 8/26

6:00 am-4:27 pm

1 stop8h 27m

$190

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 10/16

5:05 am-2:00 pm

1 stop6h 55m

$231

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 8/30

1:45 pm-10:15 am

2 stops18h 30m

$239

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 10/26

6:34 pm-1:28 pm

2 stops16h 54m

$267

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 10/16

9:40 pm-9:35 pm

2 stops21h 55m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 25, 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 27 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, January is the cheapest month in which you can book a flight from Portland to Madison (average of $338). Flying from Portland to Madison in March is currently the most expensive (average of $422). 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 July 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 49% 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 July 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
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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.
Sun Country Air
6.9
Okay
333 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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 Portland to Madison. 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 Portland to Madison round-trip?

    Cheapflights users have booked flights from Portland to Madison round-trip from $218. Other airlines that can offer you cheap pricing are Delta, from $289, and American Airlines, from $379. These flights start at 50% 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 $129 on Frontier. Other airlines that offer cheap prices include Delta from $190 and American Airlines from $231 one-way.

  • What are the cheapest flights from Portland to Madison?

    The cheapest flight price from Portland to Madison is $99. On average you can expect to pay $510. 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, January is the cheapest month in which you can book a flight from Portland to Madison (average of $338). Flying from Portland to Madison in March is currently the most expensive (average of $422). 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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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$212FlexibilityNo cancel feeOn-time62%
DeltaCheapest$278Average$461FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$432FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$301Average$508FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$668FlexibilityNo cancel feeOn-time75%

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