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Madison

$68+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or September, booked 11 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap 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 septiembre 11, 2025.

Round-trip from

$194
(Frontier)

One-way from

$68
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$378

Good round-trip deal

$793 or less
From Portland to Madison Truax Field
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One-way flight from Portland to Madison Truax Field
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Highest demand for flights based on searches. 8% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Portland to Madison Truax Field.
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Find 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 septiembre 11, 2025.

This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/256:05 amPDX - MSN
1 stop11h 09mFrontier
lun. 9/297:59 pmMSN - PDX
1 stop6h 13mFrontier
Deal found 9/10$194
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/296:05 amPDX - MSN
1 stop11h 09mFrontier
jue. 10/27:59 pmMSN - PDX
1 stop6h 13mFrontier
Deal found 9/10$214
This Frontier deal was found by Cheapflights users on 9/11. 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.
dom. 9/286:05 amPDX - MSN
1 stop11h 09mFrontier
vie. 10/37:59 pmMSN - PDX
1 stop6h 13mFrontier
Deal found 9/11$237
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/23:26 pmPDX - MSN
1 stop25h 49mFrontier
vie. 11/78:00 pmMSN - PDX
1 stop17h 56mFrontier
Deal found 9/10$248
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/296:05 amPDX - MSN
1 stop11h 09mFrontier
vie. 10/37:59 pmMSN - PDX
1 stop6h 13mFrontier
Deal found 9/10$250
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/266:05 amPDX - MSN
1 stop11h 09mFrontier
lun. 9/297:59 pmMSN - PDX
1 stop6h 13mFrontier
Deal found 9/10$278
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/111:39 amPDX - MSN
1 stop6h 42mDelta
sáb. 11/82:42 pmMSN - PDX
1 stop7h 44mDelta
Deal found 9/11$289
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/212:40 amPDX - MSN
1 stop7h 38mDelta
mar. 11/46:00 amMSN - PDX
1 stop7h 01mDelta
Deal found 9/11$295
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/313:26 pmPDX - MSN
2 stops15h 42mMultiple Airlines
vie. 11/78:00 pmMSN - PDX
1 stop17h 56mMultiple Airlines
Deal found 9/10$312
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3012:40 amPDX - MSN
1 stop7h 38mDelta
sáb. 11/82:42 pmMSN - PDX
1 stop7h 44mDelta
Deal found 9/10$316
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/15:30 amPDX - MSN
2 stops12h 51mDelta
mié. 11/52:42 pmMSN - PDX
1 stop7h 44mDelta
Deal found 9/11$318

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 septiembre 11, 2025.
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

dom. 11/2

12:40 am-10:18 am

1 stop7h 38m

Madison Truax Field

sáb. 11/8

2:42 pm-8:26 pm

1 stop7h 44m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

sáb. 11/1

11:39 am-8:21 pm

1 stop6h 42m

Madison Truax Field

mar. 11/4

2:42 pm-8:26 pm

1 stop7h 44m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

sáb. 11/1

11:39 am-8:21 pm

1 stop6h 42m

Madison Truax Field

vie. 11/7

11:00 am-5:27 pm

1 stop8h 27m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

mar. 11/4

10:10 pm-10:34 am

1 stop10h 24m

Madison Truax Field

mié. 11/5

2:42 pm-8:26 pm

1 stop7h 44m

$295

PortlandMadison

PDX - MSN

PDXMSN

Portland

dom. 11/2

12:40 am-10:18 am

1 stop7h 38m

Madison Truax Field

mar. 11/4

6:00 am-11:01 am

1 stop7h 01m

$295

PortlandMadison

PDX - MSN

PDXMSN

Portland

lun. 11/3

12:40 am-10:18 am

1 stop7h 38m

Madison Truax Field

sáb. 11/8

6:00 am-8:51 pm

2 stops16h 51m

$318

PortlandMadison

PDX - MSN

PDXMSN

Portland

sáb. 11/1

5:30 am-8:21 pm

2 stops12h 51m

Madison Truax Field

mié. 11/5

2:42 pm-8:26 pm

1 stop7h 44m

$318

PortlandMadison

PDX - MSN

PDXMSN

Portland

lun. 11/3

10:10 pm-10:34 am

1 stop10h 24m

Madison Truax Field

vie. 11/7

2:42 pm-8:26 pm

1 stop7h 44m

$319

PortlandMadison

PDX - MSN

PDXMSN

Portland

vie. 10/31

5:25 pm-10:18 am

2 stops14h 53m

Madison Truax Field

mar. 11/4

6:00 am-11:01 am

1 stop7h 01m

$337

PortlandMadison

PDX - MSN

PDXMSN

Portland

lun. 10/6

12:40 am-8:37 am

1 stop5h 57m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 19 results
1
2

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 August 29, 2025.

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 11 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, January is the cheapest month in which you can book a flight from Portland to Madison (average of $338). Flying from Portland to Madison in March is currently the most expensive (average of $422). 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 PDX to MSN?

Find hourly flight availability from Portland to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 11, 2025.

One of the essential ways to save on airfare from Portland to Madison is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 49% on airfare.

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 septiembre 11, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and United 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
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,177 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 38m. 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 $108. Other airlines that can offer you cheap pricing are Delta, from $278, and American Airlines, from $283. These flights start at 76% lower than the current average price 3 months from now.

  • What are the cheapest flights from Portland to Madison?

    The cheapest flight price from Portland to Madison is $775. On average you can expect to pay $793. The most popular route, (Portland - Madison Truax Field), can usually be booked for $289.

  • 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, January is the cheapest month in which you can book a flight from Portland to Madison (average of $338). Flying from Portland to Madison in March is currently the most expensive (average of $422). 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 5 airlines flying from Portland to Madison

Discover the top 5 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$278Average$454FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$454FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$497FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$739FlexibilityNo cancel feeOn-time75%

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