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Cheap flights from Portland to Madison from $166

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 9/8. 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
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.
Delta Logo
12:25 am - 8:22 amPDX  Portland-MSN Madison Truax Field
5h 57m1 stop Minneapolis St Paul
Delta Logo
12:00 pm - 5:31 pmMSN  Madison Truax Field-PDX Portland
7h 31m1 stop Minneapolis St Paul
$331Delta
Thu, Sep 10 - Tue, Sep 22
American Airlines Logo
11:08 pm - 8:14 amPDX  Portland-MSN Madison Truax Field
7h 06m1 stop Chicago O'Hare Intl
American Airlines Logo
5:53 pm - 11:39 pmMSN  Madison Truax Field-PDX Portland
7h 46m1 stop Dallas/Fort Worth
$331American Airlines
Tue, Sep 29 - Sat, Oct 10
United Airlines Logo
5:00 am - 1:13 pmPDX  Portland-MSN Madison Truax Field
6h 13m1 stop Denver Intl
United Airlines Logo
5:00 am - 9:29 amMSN  Madison Truax Field-PDX Portland
6h 29m1 stop Chicago O'Hare Intl
$331United Airlines
Sat, Sep 19 - Wed, Sep 23
United Airlines Logo
11:02 pm - 9:40 amPDX  Portland-MSN Madison Truax Field
8h 38m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 9:29 amMSN  Madison Truax Field-PDX Portland
6h 29m1 stop Chicago O'Hare Intl
$331United Airlines
Sat, Sep 19 - Wed, Sep 23
American Airlines Logo
11:49 pm - 10:55 amPDX  Portland-MSN Madison Truax Field
9h 06m1 stop Dallas/Fort Worth
American Airlines Logo
5:53 pm - 11:39 pmMSN  Madison Truax Field-PDX Portland
7h 46m1 stop Dallas/Fort Worth
$331American Airlines
Sat, Oct 10 - Wed, Oct 14
Delta Logo
11:35 am - 9:30 pmPDX  Portland-MSN Madison Truax Field
7h 55m1 stop Minneapolis St Paul
Delta Logo
6:00 am - 10:49 amMSN  Madison Truax Field-PDX Portland
6h 49m1 stop Minneapolis St Paul
$345Delta
Thu, Sep 10 - Sun, Sep 13
Frontier Logo
5:56 pm - 7:10 pmPDX  Portland-MSN Madison Truax Field
23h 14m1 stop Denver Intl
Frontier Logo
7:55 pm - 5:11 pmMSN  Madison Truax Field-PDX Portland
23h 16m1 stop Denver Intl
$362Frontier
Wed, Aug 19 - Sun, Aug 23
Multiple Airlines Logo
1:47 pm - 7:15 pmPDX  Portland-MSN Madison Truax Field
51h 28m2 stops Las Vegas Harry Reid Intl Orlando
Multiple Airlines Logo
8:00 pm - 11:43 amMSN  Madison Truax Field-PDX Portland
17h 43m1 stop Denver Intl
$373Multiple Airlines
Thu, Sep 3 - Thu, Sep 10
Alaska Airlines Logo
9:13 am - 10:10 pmPDX  Portland-MSN Madison Truax Field
10h 57m2 stops San Diego Chicago O'Hare Intl
Alaska Airlines Logo
12:56 pm - 11:02 pmMSN  Madison Truax Field-PDX Portland
12h 06m2 stops Chicago O'Hare Intl Seattle/Tacoma Intl
$581Alaska Airlines
Tue, Sep 29 - Sat, Oct 3
Alaska Airlines Logo
9:32 pm - 9:22 amPDX  Portland-MSN Madison Truax Field
9h 50m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
9:48 am - 4:50 pmMSN  Madison Truax Field-PDX Portland
9h 02m1 stop Chicago O'Hare Intl
$624Alaska Airlines
Sat, Aug 22 - Wed, Aug 26

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Delta flights from Portland to Madison

Our best Delta deals on Portland to Madison flight tickets
Delta
Sep 10
PDX12:25 amPortland
5h 57m
1 stop
MSN8:22 amMadison Truax Field
Sep 22
MSN12:00 pmMadison Truax Field
7h 31m
1 stop
PDX5:31 pmPortland
$331
Delta
Sep 3
PDX3:00 pmPortland
6h 00m
1 stop
MSN11:00 pmMadison Truax Field
Sep 7
MSN6:05 amMadison Truax Field
6h 36m
1 stop
PDX10:41 amPortland
$359
Delta
Aug 27
PDX3:00 pmPortland
6h 00m
1 stop
MSN11:00 pmMadison Truax Field
Aug 30
MSN6:16 pmMadison Truax Field
7h 04m
1 stop
PDX11:20 pmPortland
$379

Frontier flights from Portland to Madison

Our best Frontier deals on Portland to Madison flight tickets
Frontier
Aug 19
PDX5:56 pmPortland
23h 14m
1 stop
MSN7:10 pmMadison Truax Field
Aug 23
MSN7:55 pmMadison Truax Field
23h 16m
1 stop
PDX5:11 pmPortland
$362
Frontier
Oct 13
PDX5:35 pmPortland
23h 12m
1 stop
MSN6:47 pmMadison Truax Field
Oct 16
MSN7:54 pmMadison Truax Field
17h 45m
2 stops
PDX11:39 amPortland
$420
Frontier
Aug 10
PDX5:36 pmPortland
23h 34m
2 stops
MSN7:10 pmMadison Truax Field
Aug 13
MSN7:55 pmMadison Truax Field
22h 56m
1 stop
PDX4:51 pmPortland
$669

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 August 8, 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 Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 9/10

12:25 am-8:22 am

1 stop5h 57m

Madison Truax Field

Tue 9/22

12:00 pm-5:31 pm

1 stop7h 31m

$331

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 9/29

11:08 pm-8:14 am

1 stop7h 06m

Madison Truax Field

Sat 10/10

5:53 pm-11:39 pm

1 stop7h 46m

$331
Quickest round-trip

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Sat 9/19

5:00 am-1:13 pm

1 stop6h 13m

Madison Truax Field

Wed 9/23

5:00 am-9:29 am

1 stop6h 29m

$331

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Sat 9/19

11:02 pm-9:40 am

1 stop8h 38m

Madison Truax Field

Wed 9/23

5:00 am-9:29 am

1 stop6h 29m

$331

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Sat 10/10

11:49 pm-10:55 am

1 stop9h 06m

Madison Truax Field

Wed 10/14

5:53 pm-11:39 pm

1 stop7h 46m

$331

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 9/10

11:35 am-9:30 pm

1 stop7h 55m

Madison Truax Field

Sun 9/13

6:00 am-10:49 am

1 stop6h 49m

$345

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 8/19

5:56 pm-7:10 pm

1 stop23h 14m

Madison Truax Field

Sun 8/23

7:55 pm-5:11 pm

1 stop23h 16m

$362

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 9/3

1:47 pm-7:15 pm

2 stops51h 28m

Madison Truax Field

Thu 9/10

8:00 pm-11:43 am

1 stop17h 43m

$373

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Tue 9/29

9:13 am-10:10 pm

2 stops10h 57m

Madison Truax Field

Sat 10/3

12:56 pm-11:02 pm

2 stops12h 06m

$581

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Sat 8/22

9:32 pm-9:22 am

2 stops9h 50m

Madison Truax Field

Wed 8/26

9:48 am-4:50 pm

1 stop9h 02m

$624

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 $374 to $568.
The lowest price recently found on this route was $331.

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 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 $510 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 $385 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 August 2026, prices for Portland to Madison flights are approximately 125% 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 52m

Direct flights

None
The fastest flight from Portland to Madison takes 5h 52m
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 52m, 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
10,089 reviews
Search United Airlines flights
DeltaPriceFrom $313Free CancellationRating
7.8
8,499 reviews
Search Delta flights
Alaska AirlinesPriceFrom $317Free CancellationRating
7.9
12,786 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $334Free CancellationRating
7.1
11,892 reviews
Search American Airlines flights

Traveling to a place near Madison?

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