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Madison

$166+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This United Airlines deal was found by Cheapflights users on 7/25. 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.
Wed 11/41:15 pm
PDX
-
MSN
1 stop5h 28m
United Airlines
Sat 11/73:08 pm
MSN
-
PDX
1 stop8h 05m
United Airlines
Deal found 7/25$326
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/811:09 pm
PDX
-
MSN
1 stop7h 05m
American Airlines
Sat 9/192:40 pm
MSN
-
PDX
1 stop7h 50m
American Airlines
Deal found 7/27$331
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Tue 10/62:27 pm
PDX
-
MSN
1 stop6h 08m
United Airlines
Tue 10/205:10 am
MSN
-
PDX
2 stops8h 55m
United Airlines
Deal found 7/25$343
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/911:08 pm
PDX
-
MSN
1 stop7h 06m
American Airlines
Sun 9/135:00 am
MSN
-
PDX
1 stop7h 55m
American Airlines
Deal found 7/27$345
This United Airlines deal was found by Cheapflights users on 7/23. 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 8/214:07 pm
PDX
-
MSN
1 stop5h 52m
United Airlines
Sat 8/292:23 pm
MSN
-
PDX
2 stops8h 42m
United Airlines
Deal found 7/23$350
This Delta deal was found by Cheapflights users on 7/23. 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 9/311:20 pm
PDX
-
MSN
1 stop7h 32m
Delta
Mon 9/76:05 am
MSN
-
PDX
1 stop6h 36m
Delta
Deal found 7/23$359
This United Airlines deal was found by Cheapflights users on 7/23. 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 8/2112:45 pm
PDX
-
MSN
1 stop5h 54m
United Airlines
Fri 8/283:55 pm
MSN
-
PDX
2 stops8h 59m
United Airlines
Deal found 7/23$364
This American Airlines deal was found by Cheapflights users on 7/23. 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 8/1711:34 pm
PDX
-
MSN
1 stop7h 43m
American Airlines
Sat 8/226:53 pm
MSN
-
PDX
1 stop7h 05m
American Airlines
Deal found 7/23$380
This United Airlines deal was found by Cheapflights users on 7/26. 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 9/87:02 am
PDX
-
MSN
1 stop5h 57m
United Airlines
Sat 9/1910:46 am
MSN
-
PDX
2 stops9h 03m
United Airlines
Deal found 7/26$382
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 8/2810:35 am
PDX
-
MSN
1 stop6h 21m
United Airlines
Mon 8/315:00 am
MSN
-
PDX
2 stops9h 00m
United Airlines
Deal found 7/26$389
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Wed 8/125:00 am
PDX
-
MSN
1 stop6h 13m
United Airlines
Wed 8/195:00 am
MSN
-
PDX
1 stop6h 29m
United Airlines
Deal found 7/25$391

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$326
(United Airlines)

One-way from

$166
(Delta)

Popular in

December

Cheapest in

February

Average price

$539
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. 5% potential increase in price ($29 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 July 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 July 27, 2026.
Use the filters below to find and compare flights from Portland to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 9/25

2:27 pm-10:35 pm

1 stop6h 08m

Madison Truax Field

Wed 10/7

5:00 am-9:31 am

1 stop6h 31m

$345

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 9/25

2:27 pm-10:35 pm

1 stop6h 08m

Madison Truax Field

Wed 9/30

5:00 am-9:31 am

1 stop6h 31m

$345

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 9/8

7:02 am-2:59 pm

1 stop5h 57m

Madison Truax Field

Sat 9/19

10:46 am-5:49 pm

2 stops9h 03m

$382

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 9/8

7:02 am-2:59 pm

1 stop5h 57m

Madison Truax Field

Tue 9/15

5:00 am-12:00 pm

2 stops9h 00m

$411

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 9/19

5:00 am-1:13 pm

1 stop6h 13m

Madison Truax Field

Wed 9/23

5:00 am-11:28 am

1 stop8h 28m

$431

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 9/9

8:40 am-8:53 pm

2 stops10h 13m

Madison Truax Field

Sun 9/13

2:44 pm-7:18 pm

1 stop6h 34m

$450

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 8/7

12:35 am-8:16 am

1 stop5h 41m

Madison Truax Field

Sun 8/16

5:07 pm-11:20 pm

1 stop8h 13m

$451

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 10/11

8:44 pm-10:10 am

2 stops11h 26m

Madison Truax Field

Tue 10/20

7:53 pm-11:44 pm

1 stop5h 51m

$468

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 8/27

8:24 pm-8:16 am

2 stops9h 52m

Madison Truax Field

Mon 8/31

6:05 am-10:41 am

1 stop6h 36m

$477
Cheapest one-way

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 9/8

12:25 am-8:22 am

1 stop5h 57m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 18 resultsSorted by cheapest first
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 July.
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?

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 74 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, February is the cheapest month in which you can book a flight from Portland to Madison (average of $398). Flying from Portland to Madison in December is currently the most expensive (average of $618). 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?

Airfare is below average for this route at the moment.

Portland to Madison flights typically cost between $368 and $550 in November.
The cheapest round-trip price found within the last 5 days was $326 on United Airlines (Nov 4-Nov 7).

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 July 27, 2026.
See what other customers who have flown with Alaska Airlines,Delta, andUnited 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.
Alaska Airlines
7.9
Good
12,719 reviews

Overall

7.9

Comfort

7.8

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Alaska Airlines
7.9
Good
12,719 reviews
Alaska Airlines
7.9
Good
12,719 reviews

Overall

7.9

Comfort

7.8

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Delta
7.8
Good
8,485 reviews
Alaska Airlines
7.9
Good
12,719 reviews

Overall

7.9

Comfort

7.8

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
United Airlines
7.4
Good
10,042 reviews
Alaska Airlines
7.9
Good
12,719 reviews

Overall

7.9

Comfort

7.8

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
American Airlines
7.1
Good
11,843 reviews
Alaska Airlines
7.9
Good
12,719 reviews

Overall

7.9

Comfort

7.8

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.

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 6h 08m. The distance between Portland and Madison is about 1639 mi.

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

    Cheapflights users have booked flights from Portland to Madison round-trip from $308. Other airlines that can offer you cheap pricing are Delta, from $313, and Alaska Airlines, from $317. These flights start at 38% 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 $161 on Frontier. Other airlines that offer cheap prices include United Airlines from $194 and Delta from $203 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, February is the cheapest month in which you can book a flight from Portland to Madison (average of $398). Flying from Portland to Madison in December is currently the most expensive (average of $618). 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
Sun Prairie
Middleton
Baraboo
Fitchburg

Browse thousands of different options on Cheapflights for your next trip

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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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$308Average$464FlexibilityNo cancel feeOn-time69%
DeltaCheapest$313Average$507FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$317Average$630FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$334Average$510FlexibilityNo cancel feeOn-time71%

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