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Madison

$169+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

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.
Tue 4/2111:23 pm
PDX
-
MSN
1 stop9h 32m
American Airlines
Sat 4/253:29 pm
MSN
-
PDX
1 stop8h 09m
American Airlines
Deal found 1/27$309
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 am
PDX
-
MSN
1 stop8h 52m
American Airlines
Mon 2/1610:54 am
MSN
-
PDX
1 stop11h 50m
American Airlines
Deal found 1/25$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.
Fri 2/2712:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Sat 3/73:45 pm
MSN
-
PDX
1 stop6h 45m
Delta
Deal found 1/27$354
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 2/106:00 am
PDX
-
MSN
1 stop6h 10m
Delta
Mon 2/166:20 am
MSN
-
PDX
1 stop8h 24m
Delta
Deal found 1/27$359
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 2/105:00 am
PDX
-
MSN
2 stops9h 44m
United Airlines
Sat 2/146:30 am
MSN
-
PDX
1 stop7h 25m
United Airlines
Deal found 1/26$364
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/211:32 pm
PDX
-
MSN
2 stops7h 19m
Delta
Sat 4/252:41 pm
MSN
-
PDX
1 stop7h 24m
Delta
Deal found 1/26$366
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3111:39 am
PDX
-
MSN
1 stop8h 18m
Delta
Tue 8/111:45 pm
MSN
-
PDX
2 stops12h 08m
Delta
Deal found 1/26$371
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1012:40 am
PDX
-
MSN
1 stop7h 39m
Delta
Mon 2/166:20 am
MSN
-
PDX
1 stop8h 24m
Delta
Deal found 1/26$379
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 4/217:32 pm
PDX
-
MSN
2 stops11h 29m
Delta
Tue 4/282:41 pm
MSN
-
PDX
2 stops11h 14m
Delta
Deal found 1/27$384
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:35 am
PDX
-
MSN
2 stops9h 13m
Delta
Sat 3/73:45 pm
MSN
-
PDX
1 stop6h 45m
Delta
Deal found 1/25$401
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:40 am
PDX
-
MSN
1 stop5h 40m
Delta
Mon 9/211:45 pm
MSN
-
PDX
2 stops12h 08m
Delta
Deal found 1/25$402

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$169
(United Airlines)

Popular in

July

Cheapest in

January

Average price

$348
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Madison Truax Field flights.
Search Deals
From Portland to Madison Truax Field
Search Deals
One-way flight from Portland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 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 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 January 27, 2026.
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

Wed 5/27

12:59 am-10:39 am

1 stop7h 40m

Madison Truax Field

Tue 6/2

2:22 pm-9:32 pm

1 stop9h 10m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 4/6

11:59 pm-10:11 am

1 stop8h 12m

Madison Truax Field

Sat 4/11

2:44 pm-10:29 pm

1 stop9h 45m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 4/21

11:23 pm-10:55 am

1 stop9h 32m

Madison Truax Field

Sat 4/25

3:29 pm-9:38 pm

1 stop8h 09m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 2/10

6:00 am-4:52 pm

1 stop8h 52m

Madison Truax Field

Mon 2/16

10:54 am-8:44 pm

1 stop11h 50m

$334

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 2/16

9:44 pm-9:53 am

1 stop10h 09m

Madison Truax Field

Thu 2/26

10:54 am-8:44 pm

1 stop11h 50m

$334

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 2/27

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Sat 3/7

3:45 pm-8:30 pm

1 stop6h 45m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 2/11

5:00 am-1:15 pm

1 stop6h 15m

Madison Truax Field

Sun 2/15

2:48 pm-10:40 pm

1 stop9h 52m

$359

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 2/11

1:53 pm-10:50 pm

1 stop6h 57m

Madison Truax Field

Mon 2/16

6:20 am-12:44 pm

1 stop8h 24m

$359

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 3/13

1:52 pm-10:50 pm

1 stop6h 58m

Madison Truax Field

Mon 3/23

3:27 pm-11:09 pm

1 stop9h 42m

$359

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 2/10

5:00 am-4:44 pm

2 stops9h 44m

Madison Truax Field

Sat 2/14

6:30 am-11:55 am

1 stop7h 25m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 22 results
1
2
3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 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 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 January 23, 2026.

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 9 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, October is the cheapest month in which you can book a flight from Portland to Madison (average of $79). Flying from Portland to Madison in March is currently the most expensive (average of $326). 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.

How much does it cost to fly round-trip from Portland to Madison?

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 January 27, 2026.
See what other customers who have flown with Delta, United Airlines, and American 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.
Delta
7.9
Good
8,119 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

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
8,119 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

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
9,205 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

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
11,197 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

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
8,119 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

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 Portland to Madison. 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 Portland to Madison?

    Departing from Portland to Madison will take you 7h 40m. The distance between Portland and Madison is about 1639 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Cheapflights users have booked flights from Portland to Madison round-trip from $149. Other airlines that can offer you cheap pricing are Delta, from $258, and American Airlines, from $283. These flights start at 67% 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 $114 on American Airlines. Other airlines that offer cheap prices include Delta from $114 and Frontier from $139 one-way.

  • 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, October is the cheapest month in which you can book a flight from Portland to Madison (average of $79). Flying from Portland to Madison in March is currently the most expensive (average of $326). 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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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 4 airlines flying from Portland to Madison

Discover the top 4 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$149Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$258Average$442FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$453FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$308Average$464FlexibilityNo cancel feeOn-time69%

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