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Cheap flights from Portland to Madison from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Madison departing on 1/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:40 am - 10:19 am
PDX
-
MSN
7h 39m1 stop
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$289Delta
Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
5:00 am - 7:07 pm
PDX
-
MSN
12h 07m2 stops
United Airlines Logo
6:30 am - 11:57 am
MSN
-
PDX
7h 27m1 stop
$294United Airlines
Fri, Jan 23 - Sun, Jan 25
United Airlines Logo
7:00 am - 2:52 pm
PDX
-
MSN
5h 52m1 stop
United Airlines Logo
8:15 am - 1:45 pm
MSN
-
PDX
7h 30m1 stop
$309United Airlines
Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
5:00 am - 1:15 pm
PDX
-
MSN
6h 15m1 stop
United Airlines Logo
6:30 am - 2:46 pm
MSN
-
PDX
10h 16m2 stops
$314United Airlines
Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
7:45 am - 7:07 pm
PDX
-
MSN
9h 22m2 stops
United Airlines Logo
6:30 am - 1:45 pm
MSN
-
PDX
9h 15m2 stops
$319United Airlines
Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
11:59 pm - 10:10 am
PDX
-
MSN
8h 11m1 stop
United Airlines Logo
3:48 pm - 10:32 pm
MSN
-
PDX
8h 44m1 stop
$321United Airlines
Thu, Jan 15 - Sun, Jan 25
United Airlines Logo
11:59 pm - 10:10 am
PDX
-
MSN
8h 11m1 stop
United Airlines Logo
12:32 pm - 6:56 pm
MSN
-
PDX
8h 24m1 stop
$334United Airlines
Thu, Jan 15 - Sun, Jan 25
Delta Logo
5:15 pm - 10:50 pm
PDX
-
MSN
27h 35m2 stops
Delta Logo
6:30 am - 12:46 pm
MSN
-
PDX
8h 16m1 stop
$354Delta
Fri, Jan 23 - Mon, Jan 26
Delta Logo
12:30 am - 10:17 am
PDX
-
MSN
7h 47m1 stop
Delta Logo
10:57 am - 5:39 pm
MSN
-
PDX
8h 42m1 stop
$359Delta
Fri, Apr 3 - Sat, Apr 11
Delta Logo
7:37 pm - 9:09 am
PDX
-
MSN
11h 32m2 stops
Delta Logo
11:00 am - 5:35 pm
MSN
-
PDX
8h 35m1 stop
$362Delta
Fri, Jan 23 - Thu, Jan 29

Alaska Airlines flights from Portland to Madison

Our best Alaska Airlines deals on Portland to Madison flight tickets
Alaska Airlines
Jan 23
PDX7:05 amPortland
7h 47m
1 stop
MSN4:52 pmMadison Truax Field
Jan 26
MSN11:29 amMadison Truax Field
7h 19m
1 stop
PDX4:48 pmPortland
$378
Find similar
Alaska Airlines
Apr 14
PDX7:40 amPortland
12h 49m
2 stops
MSN10:29 pmMadison Truax Field
Apr 16
MSN4:48 pmMadison Truax Field
19h 02m
2 stops
PDX9:50 amPortland
$617
Find similar
Alaska Airlines
Dec 25
PDX11:00 pmPortland
8h 30m
1 stop
MSN9:30 amMadison Truax Field
Dec 29
MSN6:18 pmMadison Truax Field
17h 26m
2 stops
PDX9:44 amPortland
$802
Find similar

Delta flights from Portland to Madison

Our best Delta deals on Portland to Madison flight tickets
Delta
Jan 22
PDX12:40 amPortland
7h 39m
1 stop
MSN10:19 amMadison Truax Field
Jan 25
MSN6:30 amMadison Truax Field
8h 16m
1 stop
PDX12:46 pmPortland
$289
Find similar
Delta
Jan 23
PDX5:15 pmPortland
27h 35m
2 stops
MSN10:50 pmMadison Truax Field
Jan 26
MSN6:30 amMadison Truax Field
8h 16m
1 stop
PDX12:46 pmPortland
$354
Find similar
Delta
Apr 3
PDX12:30 amPortland
7h 47m
1 stop
MSN10:17 amMadison Truax Field
Apr 11
MSN10:57 amMadison Truax Field
8h 42m
1 stop
PDX5:39 pmPortland
$359
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
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

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 1/22

12:40 am-10:19 am

1 stop7h 39m

Madison Truax Field

Sun 1/25

6:30 am-12:46 pm

1 stop8h 16m

$289

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/23

5:00 am-7:07 pm

2 stops12h 07m

Madison Truax Field

Sun 1/25

6:30 am-11:57 am

1 stop7h 27m

$294

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 1/21

7:00 am-2:52 pm

1 stop5h 52m

Madison Truax Field

Sat 1/24

8:15 am-1:45 pm

1 stop7h 30m

$309

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 1/21

5:00 am-1:15 pm

1 stop6h 15m

Madison Truax Field

Sat 1/24

6:30 am-2:46 pm

2 stops10h 16m

$314

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 1/21

7:45 am-7:07 pm

2 stops9h 22m

Madison Truax Field

Sat 1/24

6:30 am-1:45 pm

2 stops9h 15m

$319

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 1/15

11:59 pm-10:10 am

1 stop8h 11m

Madison Truax Field

Sun 1/25

3:48 pm-10:32 pm

1 stop8h 44m

$321

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 1/15

11:59 pm-10:10 am

1 stop8h 11m

Madison Truax Field

Sun 1/25

12:32 pm-6:56 pm

1 stop8h 24m

$334

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/23

5:15 pm-10:50 pm

2 stops27h 35m

Madison Truax Field

Mon 1/26

6:30 am-12:46 pm

1 stop8h 16m

$354

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 4/3

12:30 am-10:17 am

1 stop7h 47m

Madison Truax Field

Sat 4/11

10:57 am-5:39 pm

1 stop8h 42m

$359

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 1/23

7:37 pm-9:09 am

2 stops11h 32m

Madison Truax Field

Thu 1/29

11:00 am-5:35 pm

1 stop8h 35m

$362

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Madison from

How to get the cheapest flight ticket from Portland to Madison

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Madison?

The month of January is, on average, the cheapest month to fly to Madison from Portland, with most prices found around $312. If you’re not able to fly to Madison in January, then February is your next best option. Flight prices from Portland to Madison during February average around $381.

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Portland to Madison is on a Tuesday when prices can be found for as low as $424. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $592.

What is the cheapest time of day to depart on your flight to Madison?

According to our data, the cheapest time of day to fly to Madison is in the evening. momondo users have found flights departing from Portland to Madison in the evening for as low as $397. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the morning when prices are around $536.

What is the cheapest Portland to Madison Truax Field flight route?

Fly from Portland to Madison Truax Field for the best Portland - Madison Truax Field flight prices

How far in advance should I book a flight to Madison?

You are more likely to see cheaper flights to Madison from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Madison for around $454 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Madison from Portland for as low as $303 on momondo.

What cabin class options are available on Portland to Madison Truax Field flights?

There is only 1 cabin class available to choose from on Portland to Madison Truax Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Portland to Madison flights?

No. A direct flight is the cheapest option for a flight between Portland to Madison.

How have Portland to Madison flight prices changed over time?

As of December 2025, prices for Portland to Madison flights are approximately 89% more expensive when compared to flights at the same time last year.

When to book flights from Portland to Madison

Are you open to changing your travel dates? Check out the ideal times to fly from Portland to Madison according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland to Madison (PDX to MSN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Madison

Best Price Found

$793

Fastest flight time

5h 55m

Direct flights

None
The best flight deal from Portland to Madison found on momondo in the last 72 hours is $793
The fastest flight from Portland to Madison takes 5h 55m
There are no direct flights from Portland to Madison. Popular non-direct route for this connection is Portland Airport - Madison Truax Field Airport.
Search flight deals

  • How far is Portland to Madison Truax Field by plane?

    Portland and Madison Truax Field are 1641.2 mi apart from one another. Flights usually cover this in 5h 55m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Portland Airport to Madison Truax Field Airport?

    Prices for flights from Portland Airport to Madison Truax Field Airport were last updated today.

  • How many operators does momondo search for flights from Portland Airport to Madison Truax Field Airport?

  • How old do you have to be to fly from Portland Airport to Madison Truax Field Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents required for your trip to Madison Truax Field Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Madison Truax Field Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Portland to Madison?

  • What is the most popular airline from Portland to Madison?

Best airlines flying from Portland to Madison

Compare and see reviews for airlines that fly from Portland to Madison with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $149Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
DeltaPriceFrom $273Free CancellationRating
7.9
8,007 reviews
Search Delta flights
American AirlinesPriceFrom $283Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom $311Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $379Free CancellationRating
8.0
11,432 reviews
Search Alaska Airlines flights

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Portage
Fitchburg
Sun Prairie
Windsor
Cambridge
Oxford
Evansville

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Madison?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Madison from Portland.

Can I find flights from Portland to Madison with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Portland to Madison flights to just show those with flexible booking policies.

How can momondo help me find flights from Portland to Madison?

momondo helps you find the best flight between Portland and Madison by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Portland to Madison right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Portland to Madison flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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