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$190+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$289
(United Airlines)

One-way from

$190
(Delta)

Popular in

December

Cheapest in

September

Average price

$498
From Madison Truax Field to Portland
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One-way flight from Madison Truax Field to Portland
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Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/10. 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 7/96:40 amMSN - PDX
1 stop7h 03mUnited Airlines
Mon 7/1411:59 pmPDX - MSN
1 stop8h 14mUnited Airlines
Deal found 6/10$289
This CheapOair deal was found by Cheapflights users on 6/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:56 pmMSN - PDX
1 stop6h 20mMultiple Airlines
Sun 10/2611:30 amPDX - MSN
Nonstop3h 31mMultiple Airlines
Deal found 6/11$290
This Frontier deal was found by Cheapflights users on 6/11. 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 9/258:14 pmMSN - PDX
1 stop6h 02mFrontier
Thu 10/26:05 amPDX - MSN
1 stop11h 24mFrontier
Deal found 6/11$291
This Delta deal was found by Cheapflights users on 6/9. 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 7/156:45 amMSN - PDX
1 stop7h 50mDelta
Wed 7/239:30 pmPDX - MSN
1 stop10h 35mDelta
Deal found 6/9$314
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/15:40 amMSN - PDX
1 stop5h 59mAmerican Airlines
Fri 7/1112:59 amPDX - MSN
1 stop7h 47mAmerican Airlines
Deal found 6/9$339

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 June 12, 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

Wed 7/9

6:40 am-11:43 am

1 stop7h 03m

Portland

Mon 7/14

11:59 pm-10:13 am

1 stop8h 14m

$289

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 10/24

7:56 pm-12:16 am

1 stop6h 20m

Portland

Sun 10/26

11:30 am-5:01 pm

Nonstop3h 31m

$290

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 9/25

8:14 pm-12:16 am

1 stop6h 02m

Portland

Thu 10/2

6:05 am-7:29 pm

1 stop11h 24m

$291

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 7/15

6:45 am-12:35 pm

1 stop7h 50m

Portland

Mon 7/21

12:40 am-8:39 am

1 stop5h 59m

$314

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 7/1

5:40 am-9:39 am

1 stop5h 59m

Portland

Fri 7/11

12:59 am-10:46 am

1 stop7h 47m

$339

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 8/13

2:44 pm-8:58 pm

1 stop8h 14m

$190

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Mon 8/18

5:49 pm-10:59 pm

1 stop7h 10m

$199

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 7/10

7:18 pm-12:16 am

1 stop6h 58m

$229

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 7/16

10:45 am-4:35 pm

1 stop7h 50m

$235

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 8/13

2:54 pm-12:35 am

2 stops11h 41m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 11 results
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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 June 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 $368). 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 June 12, 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 June 12, 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

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Frontier
5.9
Fair
3,295 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

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, United Airlines will fly you from Madison to Portland and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Delta - these airlines can fly you to your destination from $291 and $314, respectively. These flights start at 34% 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 Delta, which is currently one of the cheapest options available, starting at $190. American Airlines flights start at $199 while deals on Frontier start at $229 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 $368). 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
Vancouver
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Longview
Hood River
Depoe Bay
Woodburn
Stevenson
Pacific City
Troutdale

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$127Average$218FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$275Average$426FlexibilityNo cancel feeOn-time71%
DeltaCheapest$283Average$423FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$288Average$480FlexibilityNo cancel feeOn-time69%

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