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$94+ Cheap flights from Madison to Portland (MSN - PDX)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
May 20 — May 271
Tue 5/20
Tue 5/27
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in September or November, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Madison to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Portland (PDX). 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 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(Delta)

One-way from

$94
(Frontier)

Popular in

July

Cheapest in

September

Average price

$403
Provider with most accurate pricing for Madison Truax Field-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Portland flights.
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From Madison Truax Field to Portland
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One-way flight from Madison Truax Field to Portland
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Madison to Portland

Cheapest flights from Madison to Portland
Explore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2025.

This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/232:00 pmMSN - PDX
1 stop9h 54mDelta
Mon 9/299:45 pmPDX - MSN
1 stop10h 30mDelta
Deal found 5/15$289
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Tue 9/24:30 pmMSN - PDX
2 stops10h 15mUnited Airlines
Sat 9/137:00 amPDX - MSN
1 stop6h 07mUnited Airlines
Deal found 5/14$294
This Frontier deal was found by Cheapflights users on 5/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:56 pmMSN - PDX
1 stop6h 20mFrontier
Sun 10/266:05 amPDX - MSN
1 stop10h 51mFrontier
Deal found 5/14$300
This American Airlines deal was found by Cheapflights users on 5/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/25:40 amMSN - PDX
1 stop5h 59mAmerican Airlines
Fri 7/1111:54 pmPDX - MSN
1 stop7h 15mAmerican Airlines
Deal found 5/15$349
This Alaska Airlines deal was found by Cheapflights users on 5/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/243:28 pmMSN - PDX
2 stops20h 17mAlaska Airlines
Sat 5/319:49 pmPDX - MSN
2 stops21h 41mAlaska Airlines
Deal found 5/15$573
This Expedia deal was found by Cheapflights users on 5/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/227:10 pmMSN - PDX
1 stop7h 09mMultiple Airlines
Sat 6/287:00 amPDX - MSN
2 stops14h 09mMultiple Airlines
Deal found 5/14$632

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Portland 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 15, 2025.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Madison

Fly to

Portland

Route

Depart

Return

Price

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 9/23

2:00 pm-9:54 pm

1 stop9h 54m

Portland

Mon 9/29

9:45 pm-10:15 am

1 stop10h 30m

$289

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 9/2

4:30 pm-12:45 am

2 stops10h 15m

Portland

Sat 9/13

7:00 am-3:07 pm

1 stop6h 07m

$294

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 10/23

7:56 pm-12:16 am

1 stop6h 20m

Portland

Sun 10/26

6:05 am-6:56 pm

1 stop10h 51m

$300

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 7/2

5:40 am-9:39 am

1 stop5h 59m

Portland

Tue 7/8

11:54 pm-10:12 am

1 stop8h 18m

$349

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sun 6/22

7:10 pm-12:19 am

1 stop7h 09m

Portland

Sat 6/28

7:00 am-11:09 pm

2 stops14h 09m

$632

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 10/22

2:45 pm-11:58 pm

2 stops11h 13m

Portland

Sun 10/26

5:30 pm-11:59 am

2 stops16h 29m

$651

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 8/14

7:11 pm-12:16 am

1 stop7h 05m

$94

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 5/28

6:17 pm-11:25 pm

1 stop7h 08m

$115

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 8/5

6:40 am-2:40 pm

2 stops10h 00m

$200

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 8/13

11:13 am-4:47 pm

1 stop7h 34m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 13 results
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Compare providers for flights from Madison to Portland

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 Madison to Portland in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 Madison-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Portland 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 Madison-Portland 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 Madison to Portland

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

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

Use this chart to determine the optimal time to book a round-trip flight from Madison to Portland. Price data was last updated on May 9, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 42 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, November is the cheapest month in which you can book a flight from Madison to Portland (average of $277). Flying from Madison to Portland in March is currently the most expensive (average of $369). 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 MSN to PDX?

Find hourly flight availability from Madison to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 15, 2025.

One of the essential ways to save on airfare from Madison to Portland is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 56% on airfare.

Rainfall in Portland by month

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

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated May 15, 2025.
See what other customers who have flown with Alaska Airlines, Delta and United Airlines from Madison to Portland 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

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

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

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

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
8,731 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

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

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
346 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Crew

8.5

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 Madison to Portland. 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 Madison to Portland round-trip?

    Currently priced at $289, Delta will fly you from Madison to Portland and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Frontier - these airlines can fly you to your destination from $294 and $300, respectively. These flights start at 35% lower than the current average price 3 months from now.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $94. Delta flights start at $115 while deals on United Airlines start at $200 one-way.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Madison to Portland (average of $277). Flying from Madison to Portland in March is currently the most expensive (average of $369). 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
Seaside
Lincoln City
Beaverton
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Wilsonville

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Top 4 airlines flying from Madison to Portland

Discover the top 4 airlines that operate flights from Madison to Portland. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$238FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$426FlexibilityNo cancel feeOn-time71%
DeltaCheapest$283Average$428FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$296Average$492FlexibilityNo cancel feeOn-time69%

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