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$115+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
May 18 — May 251
Sun 5/18
Sun 5/25
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or September, booked 87 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 May 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$259
(Delta)

One-way from

$115
(Delta)

Popular in

July

Cheapest in

January

Average price

$461

Good round-trip deal

$793 or less
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
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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. 7% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 13, 2025.

This Delta deal was found by Cheapflights users on 5/13. 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.
Thu 5/2912:40 amPDX - MSN
1 stop7h 41mDelta
Tue 6/36:17 pmMSN - PDX
1 stop7h 08mDelta
Deal found 5/13$259
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Mon 5/2611:49 pmPDX - MSN
1 stop6h 12mAmerican Airlines
Mon 8/45:30 amMSN - PDX
1 stop6h 21mAmerican Airlines
Deal found 5/12$314
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:35 amPDX - MSN
1 stop9h 51mFrontier
Thu 7/177:11 pmMSN - PDX
1 stop7h 05mFrontier
Deal found 5/12$328
This United Airlines deal was found by Cheapflights users on 5/13. 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 5/308:30 amPDX - MSN
1 stop8h 46mUnited Airlines
Tue 6/33:09 pmMSN - PDX
2 stops11h 21mUnited Airlines
Deal found 5/13$354
This Expedia deal was found by Cheapflights users on 5/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/227:00 amPDX - MSN
2 stops14h 11mMultiple Airlines
Sun 7/277:11 pmMSN - PDX
1 stop7h 05mMultiple Airlines
Deal found 5/12$500
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/47:21 amPDX - MSN
2 stops14h 05mAlaska Airlines
Mon 6/92:08 pmMSN - PDX
2 stops11h 36mAlaska Airlines
Deal found 5/12$621

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 May 13, 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

Thu 5/29

12:40 am-10:21 am

1 stop7h 41m

Madison Truax Field

Tue 6/3

6:17 pm-11:25 pm

1 stop7h 08m

$259

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 5/26

11:49 pm-8:01 am

1 stop6h 12m

Madison Truax Field

Mon 8/4

5:30 am-9:51 am

1 stop6h 21m

$314

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 7/8

6:35 am-6:26 pm

1 stop9h 51m

Madison Truax Field

Thu 7/17

7:11 pm-12:16 am

1 stop7h 05m

$328

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 5/30

8:30 am-7:16 pm

1 stop8h 46m

Madison Truax Field

Tue 6/3

3:09 pm-12:30 am

2 stops11h 21m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 7/22

7:00 am-11:11 pm

2 stops14h 11m

Madison Truax Field

Sun 7/27

7:11 pm-12:16 am

1 stop7h 05m

$500

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 6/4

7:21 am-11:26 pm

2 stops14h 05m

Madison Truax Field

Mon 6/9

2:08 pm-11:44 pm

2 stops11h 36m

$621

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 5/30

12:40 am-10:21 am

1 stop7h 41m

$115

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 5/28

8:45 am-10:18 pm

2 stops11h 33m

$120

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 5/18

6:35 am-7:06 pm

1 stop10h 31m

$136

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 6/14

12:09 am-9:20 am

1 stop7h 11m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 11 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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Madison flight deals on Cheapflights vs. FlightHub >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 Priceline the most. Priceline 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 May 9, 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 87 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 June is currently the most expensive (average of $423). 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 May 13, 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.

What is the cheapest day to fly from Portland to Madison?

Use this chart to determine the cheapest time to fly round-trip from Portland to Madison. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Madison flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 May 13, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,949 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,726 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Frontier
6.0
Okay
3,284 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $259. Other airlines that can offer you cheap pricing are American Airlines, from $314, and Frontier, from $328. These flights start at 42% 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 $115 on Delta. Other airlines that offer cheap prices include United Airlines from $120 and Frontier from $136 one-way.

  • 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, 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 June is currently the most expensive (average of $423). 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
Portage
Middleton
Baraboo

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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 May 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$263Average$449FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$312Average$528FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$668FlexibilityNo cancel feeOn-time75%

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