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Cheap flights from Portland to Madison from $288

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:18 am - 1:57 pmPDX  Portland-MSN Madison Truax Field
6h 39m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 12:22 pmMSN  Madison Truax Field-PDX Portland
9h 22m1 stop Chicago O'Hare Intl
$351American Airlines
Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
11:49 pm - 10:55 amPDX  Portland-MSN Madison Truax Field
9h 06m1 stop Dallas/Fort Worth
American Airlines Logo
11:37 am - 5:48 pmMSN  Madison Truax Field-PDX Portland
8h 11m1 stop Dallas/Fort Worth
$351American Airlines
Tue, Oct 20 - Tue, Nov 3
United Airlines Logo
8:30 am - 5:14 pmPDX  Portland-MSN Madison Truax Field
6h 44m1 stop Chicago O'Hare Intl
United Airlines Logo
2:40 pm - 9:10 pmMSN  Madison Truax Field-PDX Portland
8h 30m1 stop Denver Intl
$351United Airlines
Sat, Oct 17 - Sat, Oct 24
United Airlines Logo
5:00 am - 1:18 pmPDX  Portland-MSN Madison Truax Field
6h 18m1 stop Denver Intl
United Airlines Logo
6:42 am - 11:33 amMSN  Madison Truax Field-PDX Portland
6h 51m1 stop Chicago O'Hare Intl
$351United Airlines
Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
11:49 pm - 10:55 amPDX  Portland-MSN Madison Truax Field
9h 06m1 stop Dallas/Fort Worth
American Airlines Logo
5:00 am - 12:22 pmMSN  Madison Truax Field-PDX Portland
9h 22m1 stop Chicago O'Hare Intl
$351American Airlines
Tue, Oct 20 - Sat, Oct 24
Delta Logo
11:12 pm - 8:47 amPDX  Portland-MSN Madison Truax Field
7h 35m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 12:38 pmMSN  Madison Truax Field-PDX Portland
8h 38m1 stop Minneapolis St Paul
$379Delta
Fri, Oct 23 - Thu, Oct 29
Delta Logo
11:51 am - 7:06 pmPDX  Portland-MSN Madison Truax Field
5h 15m1 stop Minneapolis St Paul
Delta Logo
7:49 pm - 11:46 pmMSN  Madison Truax Field-PDX Portland
5h 57m1 stop Minneapolis St Paul
$379Delta
Fri, Nov 6 - Mon, Nov 9
Alaska Airlines Logo
9:03 am - 11:43 pmPDX  Portland-MSN Madison Truax Field
12h 40m2 stops San Diego Chicago O'Hare Intl
Alaska Airlines Logo
9:15 am - 4:50 pmMSN  Madison Truax Field-PDX Portland
9h 35m1 stop Chicago O'Hare Intl
$616Alaska Airlines
Tue, Nov 10 - Sat, Nov 14
Alaska Airlines Logo
7:37 pm - 10:52 amPDX  Portland-MSN Madison Truax Field
13h 15m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
5:00 am - 1:50 pmMSN  Madison Truax Field-PDX Portland
10h 50m2 stops Chicago O'Hare Intl San Diego
$621Alaska Airlines
Tue, Oct 6 - Sat, Oct 10
Sun Country Air Logo
6:26 pm - 2:00 pmPDX  Portland-MSN Madison Truax Field
41h 34m2 stops Minneapolis St Paul Phoenix Sky Harbor Intl
Sun Country Air Logo
3:02 pm - 5:20 pmMSN  Madison Truax Field-PDX Portland
52h 18m2 stops Phoenix Sky Harbor Intl Minneapolis St Paul
$968Sun Country Air
Wed, Dec 23 - Tue, Dec 29

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United Airlines flights from Portland to Madison

Our best United Airlines deals on Portland to Madison flight tickets
United Airlines
Oct 20
PDX2:27 pmPortland
6h 08m
1 stop
MSN10:35 pmMadison Truax Field
Oct 24
MSN5:00 amMadison Truax Field
8h 33m
1 stop
PDX11:33 amPortland
$351
United Airlines
Oct 20
PDX2:27 pmPortland
6h 08m
1 stop
MSN10:35 pmMadison Truax Field
Oct 24
MSN5:10 amMadison Truax Field
9h 00m
2 stops
PDX12:10 pmPortland
$356
United Airlines
Oct 14
PDX2:27 pmPortland
6h 08m
1 stop
MSN10:35 pmMadison Truax Field
Oct 17
MSN5:10 amMadison Truax Field
9h 00m
2 stops
PDX12:10 pmPortland
$370

American Airlines flights from Portland to Madison

Our best American Airlines deals on Portland to Madison flight tickets
American Airlines
Oct 11
PDX5:18 amPortland
6h 39m
1 stop
MSN1:57 pmMadison Truax Field
Oct 20
MSN8:00 amMadison Truax Field
7h 39m
1 stop
PDX1:39 pmPortland
$365
American Airlines
Oct 7
PDX5:20 amPortland
9h 53m
1 stop
MSN5:13 pmMadison Truax Field
Oct 13
MSN5:53 pmMadison Truax Field
7h 46m
1 stop
PDX11:39 pmPortland
$411
American Airlines
Oct 8
PDX5:10 amPortland
6h 47m
1 stop
MSN1:57 pmMadison Truax Field
Oct 10
MSN5:53 pmMadison Truax Field
7h 46m
1 stop
PDX11:39 pmPortland
$414

momondo Fare Finder

 
Use the filters below to find and compare flights from Portland to Madison that are best for you.

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Route

Depart

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Price

Cheapest round-trip

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 10/21

5:18 am-1:57 pm

1 stop6h 39m

Madison Truax Field

Sat 10/24

5:00 am-12:22 pm

1 stop9h 22m

$351

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 10/20

11:49 pm-10:55 am

1 stop9h 06m

Madison Truax Field

Tue 11/3

11:37 am-5:48 pm

1 stop8h 11m

$351

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Sat 10/17

8:30 am-5:14 pm

1 stop6h 44m

Madison Truax Field

Sat 10/24

2:40 pm-9:10 pm

1 stop8h 30m

$351

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 10/21

5:00 am-1:18 pm

1 stop6h 18m

Madison Truax Field

Sat 10/24

6:42 am-11:33 am

1 stop6h 51m

$351

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 10/20

11:49 pm-10:55 am

1 stop9h 06m

Madison Truax Field

Sat 10/24

5:00 am-12:22 pm

1 stop9h 22m

$351

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Fri 10/23

11:12 pm-8:47 am

1 stop7h 35m

Madison Truax Field

Thu 10/29

6:00 am-12:38 pm

1 stop8h 38m

$379
Quickest round-trip

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Fri 11/6

11:51 am-7:06 pm

1 stop5h 15m

Madison Truax Field

Mon 11/9

7:49 pm-11:46 pm

1 stop5h 57m

$379

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 11/10

9:03 am-11:43 pm

2 stops12h 40m

Madison Truax Field

Sat 11/14

9:15 am-4:50 pm

1 stop9h 35m

$616

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 10/6

7:37 pm-10:52 am

2 stops13h 15m

Madison Truax Field

Sat 10/10

5:00 am-1:50 pm

2 stops10h 50m

$621

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 12/23

6:26 pm-2:00 pm

2 stops41h 34m

Madison Truax Field

Tue 12/29

3:02 pm-5:20 pm

2 stops52h 18m

$968

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?

Prices are currently low for flights on this route.

Typical prices usually range from $386 to $545.
The lowest price recently found on this route was $351.

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 $399. If you’re not able to fly to Madison in February, then April is your next best option. Flight prices from Portland to Madison during April average around $426.

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 $504 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 $379 on momondo.

Can stopping save me money on Portland to Madison flights?

You could potentially save up to 44% on your flight if you consider stops on a Portland to Madison flight.

How have Portland to Madison flight prices changed over time?

As of September 2026, prices for Portland to Madison flights are approximately 82% 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

$288

Fastest flight time

5h 10m

Direct flights

None
The best one-way flight to Madison from Portland in the past 72 hours is $288. The best round-trip flight deal from Portland to Madison found on momondo in the last 72 hours is $351.
The fastest flight from Portland to Madison takes 5h 10m
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 10m, 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
United AirlinesPriceFrom $309Free CancellationRating
7.4
10,222 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $317Free CancellationRating
7.9
12,953 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $335Free CancellationRating
7.0
12,076 reviews
Search American Airlines flights
DeltaPriceFrom $337Free CancellationRating
7.8
8,597 reviews
Search Delta flights

Traveling to a place near Madison?

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

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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