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$88+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Jul 13 — Jul 201
Sun 7/13
Sun 7/20
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 29 days in advance, depart on a Tuesday or Saturday and return on a Tuesday

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 July 8, 2025.

Round-trip from

$215
(Priceline)

One-way from

$88
(Priceline)

Popular in

July

Cheapest in

January

Average price

$574

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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 8, 2025.

This Priceline deal was found by Cheapflights users on 7/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/286:27 amPDX - MSN
1 stop10h 24mFrontier
Sun 8/317:01 pmMSN - PDX
1 stop7h 14mFrontier
Deal found 7/8$215
This American Airlines deal was found by Cheapflights users on 7/7. 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 8/271:20 pmPDX - MSN
1 stop17h 58mAmerican Airlines
Mon 9/18:14 pmMSN - PDX
1 stop15h 32mAmerican Airlines
Deal found 7/7$273
This Delta deal was found by Cheapflights users on 7/8. 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.
Sun 8/1012:46 amPDX - MSN
1 stop5h 48mDelta
Tue 8/192:44 pmMSN - PDX
1 stop8h 15mDelta
Deal found 7/8$283
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Thu 8/215:00 amPDX - MSN
2 stops8h 02mUnited Airlines
Sun 8/245:33 pmMSN - PDX
1 stop6h 52mUnited Airlines
Deal found 7/8$288

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 8, 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

Thu 8/28

6:27 am-6:51 pm

1 stop10h 24m

Madison Truax Field

Sun 8/31

7:01 pm-12:15 am

1 stop7h 14m

$215

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 8/27

1:20 pm-9:18 am

1 stop17h 58m

Madison Truax Field

Mon 9/1

8:14 pm-9:46 am

1 stop15h 32m

$273

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 8/10

12:46 am-8:34 am

1 stop5h 48m

Madison Truax Field

Tue 8/19

2:44 pm-8:59 pm

1 stop8h 15m

$283

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 8/21

5:00 am-3:02 pm

2 stops8h 02m

Madison Truax Field

Sun 8/24

5:33 pm-10:25 pm

1 stop6h 52m

$288

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 7/13

6:35 am-6:33 pm

1 stop9h 58m

$88

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 8/5

12:40 am-8:39 am

1 stop5h 59m

$139

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sun 8/17

11:59 pm-10:33 am

1 stop8h 34m

$239

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 8/5

7:35 pm-10:13 am

2 stops12h 38m

$240

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 8/8

10:23 am-5:45 pm

3 stops29h 22m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

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 June 27, 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 29 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 July 8, 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.

What is the cheapest day to fly from Portland to Madison?

Use this chart to determine the cheapest time to fly round-trip from Portland to Madison. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Madison flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 8, 2025.
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
8.0
Very good
7,958 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,958 reviews
Delta
8.0
Very good
7,958 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,844 reviews
Delta
8.0
Very good
7,958 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,958 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.9
Fair
3,273 reviews
Delta
8.0
Very good
7,958 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    Cheapflights users have booked flights from Portland to Madison round-trip from $215. Other airlines that can offer you cheap pricing are American Airlines, from $273, and United Airlines, from $288. These flights start at 51% 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 $88 on Frontier. Other airlines that offer cheap prices include Delta from $139 and American Airlines from $239 one-way.

  • 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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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 July 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$109Average$213FlexibilityNo cancel feeOn-time62%
DeltaCheapest$278Average$475FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$433FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$507FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$379Average$668FlexibilityNo cancel feeOn-time75%

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