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Cheap flights from Portland to Madison from $209

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 5/19. 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
1:45 pm - 11:00 pm
PDX
-
MSN
7h 15m
1 stop
Delta Logo
2:45 pm - 8:15 pm
MSN
-
PDX
7h 30m
1 stop
$321Delta
Wed, Jul 22 - Tue, Jul 28
United Airlines Logo
10:40 pm - 8:55 am
PDX
-
MSN
8h 15m
1 stop
United Airlines Logo
5:00 am - 9:34 am
MSN
-
PDX
6h 34m
1 stop
$335United Airlines
Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
12:40 am - 10:38 am
PDX
-
MSN
7h 58m
1 stop
American Airlines Logo
5:11 pm - 10:53 pm
MSN
-
PDX
7h 42m
1 stop
$345American Airlines
Mon, May 25 - Sat, May 30
American Airlines Logo
11:43 pm - 10:38 am
PDX
-
MSN
8h 55m
1 stop
American Airlines Logo
6:44 pm - 11:52 pm
MSN
-
PDX
7h 08m
1 stop
$349American Airlines
Tue, May 26 - Sun, May 31
United Airlines Logo
4:15 pm - 11:59 pm
PDX
-
MSN
5h 44m
1 stop
United Airlines Logo
10:40 am - 5:46 pm
MSN
-
PDX
9h 06m
2 stops
$363United Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
3:31 pm - 12:13 am
PDX
-
MSN
6h 42m
1 stop
American Airlines Logo
5:11 pm - 12:55 am
MSN
-
PDX
9h 44m
1 stop
$367American Airlines
Fri, Jul 3 - Sat, Jul 11
Delta Logo
12:33 am - 8:11 am
PDX
-
MSN
5h 38m
1 stop
Delta Logo
6:00 am - 10:41 am
MSN
-
PDX
6h 41m
1 stop
$369Delta
Thu, Jul 16 - Mon, Jul 20
Delta Logo
12:33 am - 10:12 am
PDX
-
MSN
7h 39m
1 stop
Delta Logo
6:00 am - 10:42 am
MSN
-
PDX
6h 42m
1 stop
$380Delta
Fri, Jul 3 - Sat, Jul 11
American Airlines Logo
10:57 pm - 7:51 am
PDX
-
MSN
6h 54m
1 stop
American Airlines Logo
5:11 pm - 10:51 pm
MSN
-
PDX
7h 40m
1 stop
$381American Airlines
Sat, Jul 18 - Wed, Jul 22
Delta Logo
9:39 pm - 10:16 am
PDX
-
MSN
10h 37m
1 stop
Delta Logo
11:48 am - 5:15 pm
MSN
-
PDX
7h 27m
1 stop
$384Delta
Fri, May 15 - Sun, May 24

Delta flights from Portland to Madison

Our best Delta deals on Portland to Madison flight tickets
Delta
Jul 22
PDX1:45 pmPortland
7h 15m
1 stop
MSN11:00 pmMadison Truax Field
Jul 28
MSN2:45 pmMadison Truax Field
7h 30m
1 stop
PDX8:15 pmPortland
$321
Delta
Jul 16
PDX12:33 amPortland
5h 38m
1 stop
MSN8:11 amMadison Truax Field
Jul 20
MSN6:00 amMadison Truax Field
6h 41m
1 stop
PDX10:41 amPortland
$369
Delta
Jul 3
PDX12:33 amPortland
7h 39m
1 stop
MSN10:12 amMadison Truax Field
Jul 11
MSN6:00 amMadison Truax Field
6h 42m
1 stop
PDX10:42 amPortland
$380

Alaska Airlines flights from Portland to Madison

Our best Alaska Airlines deals on Portland to Madison flight tickets
Alaska Airlines
Jul 21
PDX10:59 pmPortland
6h 52m
1 stop
MSN7:51 amMadison Truax Field
Jul 30
MSN5:00 amMadison Truax Field
6h 45m
1 stop
PDX9:45 amPortland
$435
Alaska Airlines
Jun 25
PDX10:59 pmPortland
6h 46m
1 stop
MSN7:45 amMadison Truax Field
Jun 30
MSN5:00 amMadison Truax Field
6h 45m
1 stop
PDX9:45 amPortland
$449
Alaska Airlines
Jul 3
PDX10:59 pmPortland
6h 52m
1 stop
MSN7:51 amMadison Truax Field
Jul 11
MSN2:38 pmMadison Truax Field
10h 57m
2 stops
PDX11:35 pmPortland
$454

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 May 3, 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

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 7/22

1:45 pm-11:00 pm

1 stop7h 15m

Madison Truax Field

Tue 7/28

2:45 pm-8:15 pm

1 stop7h 30m

$321

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 7/3

10:40 pm-8:55 am

1 stop8h 15m

Madison Truax Field

Sat 7/11

5:00 am-9:34 am

1 stop6h 34m

$335

PortlandMadison

PDX - MSN

PDXMSN

Portland

Mon 5/25

12:40 am-10:38 am

1 stop7h 58m

Madison Truax Field

Sat 5/30

5:11 pm-10:53 pm

1 stop7h 42m

$345

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 5/26

11:43 pm-10:38 am

1 stop8h 55m

Madison Truax Field

Sun 5/31

6:44 pm-11:52 pm

1 stop7h 08m

$349

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 5/28

4:15 pm-11:59 pm

1 stop5h 44m

Madison Truax Field

Tue 6/2

10:40 am-5:46 pm

2 stops9h 06m

$363

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 7/3

3:31 pm-12:13 am

1 stop6h 42m

Madison Truax Field

Sat 7/11

5:11 pm-12:55 am

1 stop9h 44m

$367
Quickest round-trip

PortlandMadison

PDX - MSN

PDXMSN

Portland

Thu 7/16

12:33 am-8:11 am

1 stop5h 38m

Madison Truax Field

Mon 7/20

6:00 am-10:41 am

1 stop6h 41m

$369

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 7/3

12:33 am-10:12 am

1 stop7h 39m

Madison Truax Field

Sat 7/11

6:00 am-10:42 am

1 stop6h 42m

$380

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 7/18

10:57 pm-7:51 am

1 stop6h 54m

Madison Truax Field

Wed 7/22

5:11 pm-10:51 pm

1 stop7h 40m

$381

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 5/15

9:39 pm-10:16 am

1 stop10h 37m

Madison Truax Field

Sun 5/24

11:48 am-5:15 pm

1 stop7h 27m

$384

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 typical price of a round-trip flight between Portland and Madison?

What is the cheapest month to fly to Madison?

The month of February is, on average, the cheapest month to fly to Madison from Portland, with most prices found around $398. If you’re not able to fly to Madison in February, then October is your next best option. Flight prices from Portland to Madison during October average around $409.

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 from Portland 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 $479 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 $274 on momondo.

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 May 2026, prices for Portland to Madison flights are approximately 63% 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

Fastest flight time

5h 38m

Direct flights

None
The fastest flight from Portland to Madison takes 5h 38m
There are no direct flights from Portland to Madison. There are no popular flight routes from Portland to Madison.
Search flight deals

Frequently asked questions about flying from Portland to Madison

  • 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 38m, 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 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
5.6
2,970 reviews
Search Frontier flights
DeltaPriceFrom $288Free CancellationRating
7.9
8,460 reviews
Search Delta flights
American AirlinesPriceFrom $288Free CancellationRating
7.1
11,673 reviews
Search American Airlines flights
United AirlinesPriceFrom $308Free CancellationRating
7.4
9,684 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $379Free CancellationRating
7.9
12,320 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
Sun Prairie
Middleton
Fitchburg
Portage
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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