HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$169+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 January 27, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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 9/225:50 pm
MSN
-
PDX
1 stop6h 48m
United Airlines
Tue 9/2912:40 pm
PDX
-
MSN
1 stop6h 59m
United Airlines
Deal found 1/26$305
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:20 am
MSN
-
PDX
1 stop8h 24m
Delta
Sat 3/712:05 am
PDX
-
MSN
1 stop7h 00m
Delta
Deal found 1/27$309
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 2/1910:54 am
MSN
-
PDX
1 stop11h 50m
American Airlines
Thu 2/2611:40 pm
PDX
-
MSN
1 stop8h 56m
American Airlines
Deal found 1/27$317
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/215:44 pm
MSN
-
PDX
1 stop7h 12m
United Airlines
Wed 2/258:30 am
PDX
-
MSN
2 stops10h 37m
United Airlines
Deal found 1/25$325
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:30 am
MSN
-
PDX
1 stop7h 27m
United Airlines
Wed 3/47:00 am
PDX
-
MSN
1 stop5h 57m
United Airlines
Deal found 1/27$334
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:20 am
MSN
-
PDX
1 stop8h 24m
Delta
Tue 3/39:45 pm
PDX
-
MSN
1 stop10h 38m
Delta
Deal found 1/27$337
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:20 am
MSN
-
PDX
2 stops16h 35m
Delta
Wed 3/412:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Deal found 1/27$348
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:20 am
MSN
-
PDX
1 stop8h 24m
Delta
Sat 3/75:10 pm
PDX
-
MSN
2 stops13h 55m
Delta
Deal found 1/27$352
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/262:51 pm
MSN
-
PDX
1 stop7h 39m
Delta
Sun 3/112:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Deal found 1/27$354

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Delta)

One-way from

$169
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$443
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.
Search Deals
From Madison Truax Field to Portland
Search Deals
One-way flight from Madison Truax Field to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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

Fri 4/17

2:41 pm-8:05 pm

1 stop7h 24m

Portland

Tue 4/21

10:55 pm-10:32 am

1 stop9h 37m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 2/17

6:20 am-12:44 pm

1 stop8h 24m

Portland

Sat 2/21

6:00 am-3:00 pm

1 stop7h 00m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Fri 4/3

2:45 pm-8:25 pm

1 stop7h 40m

Portland

Mon 4/6

11:15 pm-8:51 am

1 stop7h 36m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 3/12

6:00 am-12:48 pm

1 stop8h 48m

Portland

Wed 3/18

11:15 pm-8:51 am

1 stop7h 36m

$309

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Sat 2/21

5:44 pm-10:56 pm

1 stop7h 12m

Portland

Wed 2/25

8:30 am-9:07 pm

2 stops10h 37m

$325

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 2/11

6:30 am-11:57 am

1 stop7h 27m

Portland

Wed 3/4

7:00 am-2:57 pm

1 stop5h 57m

$334

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 3/4

3:53 pm-11:14 pm

2 stops9h 21m

Portland

Fri 3/13

11:59 pm-10:12 am

1 stop8h 13m

$354

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Thu 3/19

10:48 am-5:39 pm

1 stop8h 51m

Portland

Wed 3/25

11:15 pm-8:51 am

1 stop7h 36m

$354

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Wed 7/8

5:17 pm-11:59 pm

1 stop8h 42m

Portland

Wed 7/15

12:40 am-8:20 am

1 stop5h 40m

$354

MadisonPortland

MSN - PDX

MSNPDX

Madison Truax Field

Tue 2/10

6:30 am-11:57 am

1 stop7h 27m

Portland

Sat 2/14

11:59 pm-10:14 am

1 stop8h 15m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 19 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 FlightHub the most. FlightHub 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 85 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, September is the cheapest month in which you can book a flight from Madison to Portland (average of $128). Flying from Madison to Portland in March is currently the most expensive (average of $292). 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.

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 January 27, 2026.
Read through reviews of airlines operating flights from Madison to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,123 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,123 reviews
Delta
7.9
Good
8,123 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,208 reviews
Delta
7.9
Good
8,123 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,201 reviews
Delta
7.9
Good
8,123 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,123 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Madison to Portland?

    There are many flights that can get you from Madison to Portland in 7h 12m. Fly via Delta, American Airlines, or United Airlines to get the fastest option. Madison and Portland are separated by a distance of 1639 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $214, Frontier will fly you from Madison to Portland and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $279 and $288, respectively. These flights start at 49% 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 $97. American Airlines flights start at $114 while deals on United Airlines start at $168 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, September is the cheapest month in which you can book a flight from Madison to Portland (average of $128). Flying from Madison to Portland in March is currently the most expensive (average of $292). 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
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Portland flights
Minneapolis to Portland flights
O'Hare Intl to Boise flights
Minneapolis to Boise flights
O'Hare Intl to Eugene flights
Appleton to Portland flights
O'Hare Intl to Redmond flights
Milwaukee to Portland flights
Minneapolis to Redmond flights
Minneapolis to Eugene flights
Green Bay to Portland flights
Madison to Boise flights
Green Bay to Boise flights
O'Hare Intl to Medford flights
Milwaukee to Redmond flights
Madison to Redmond flights
Duluth to Portland flights
Madison to Eugene flights
Milwaukee to Boise flights
Minneapolis to Medford flights
Milwaukee to Medford flights
Appleton to Boise flights
Rhinelander to Boise flights
Milwaukee to Eugene flights
Appleton to Medford flights
O'Hare Intl to North Bend flights
Appleton to Eugene flights
Wausau to Portland flights
Eau Claire to Portland flights
Madison to Medford flights
O'Hare Intl to Yakima flights
Minneapolis to North Bend flights
Minneapolis to Pendleton flights
La Crosse to Portland flights
Milwaukee to Yakima flights
Minneapolis to Yakima flights
Dubuque to Portland flights
La Crosse to Redmond flights
Madison to Yakima flights

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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$214Average$300FlexibilityNo cancel feeOn-time62%
DeltaCheapest$279Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$288Average$445FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$420FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.