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Cheap flights from Portland to Madison from $189

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 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
American Airlines Logo
11:40 pm - 11:05 am
PDX
-
MSN
9h 25m
1 stop
American Airlines Logo
5:42 pm - 10:56 pm
MSN
-
PDX
7h 14m
1 stop
$349American Airlines
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
12:35 pm - 7:14 pm
PDX
-
MSN
28h 39m
1 stop
Frontier Logo
6:23 pm - 11:13 am
MSN
-
PDX
18h 50m
1 stop
$361Frontier
Sat, Jun 6 - Sat, Jun 13
American Airlines Logo
6:00 am - 5:22 pm
PDX
-
MSN
9h 22m
1 stop
American Airlines Logo
5:37 pm - 11:57 pm
MSN
-
PDX
8h 20m
1 stop
$369American Airlines
Tue, Apr 21 - Sat, Apr 25
United Airlines Logo
5:00 am - 1:13 pm
PDX
-
MSN
6h 13m
1 stop
United Airlines Logo
10:49 am - 5:43 pm
MSN
-
PDX
8h 54m
2 stops
$374United Airlines
Wed, Aug 12 - Tue, Aug 18
United Airlines Logo
11:40 pm - 9:59 am
PDX
-
MSN
8h 19m
1 stop
United Airlines Logo
7:17 pm - 12:02 am
MSN
-
PDX
6h 45m
1 stop
$390United Airlines
Tue, Jul 7 - Sat, Aug 8
United Airlines Logo
5:00 am - 3:02 pm
PDX
-
MSN
8h 02m
2 stops
United Airlines Logo
5:34 pm - 11:55 pm
MSN
-
PDX
8h 21m
1 stop
$392United Airlines
Sat, May 2 - Mon, May 4
Delta Logo
12:40 am - 8:20 am
PDX
-
MSN
5h 40m
1 stop
Delta Logo
11:53 am - 3:58 pm
MSN
-
PDX
6h 05m
1 stop
$397Delta
Fri, Jun 19 - Sat, Jul 4
American Airlines Logo
5:40 am - 5:05 pm
PDX
-
MSN
9h 25m
1 stop
American Airlines Logo
5:45 pm - 12:34 am
MSN
-
PDX
8h 49m
1 stop
$399American Airlines
Sat, Mar 28 - Wed, Apr 1
United Airlines Logo
11:59 pm - 8:57 am
PDX
-
MSN
6h 58m
1 stop
United Airlines Logo
8:30 am - 3:09 pm
MSN
-
PDX
8h 39m
1 stop
$401United Airlines
Fri, Apr 17 - Mon, Apr 20
United Airlines Logo
2:41 pm - 10:58 pm
PDX
-
MSN
6h 17m
1 stop
United Airlines Logo
5:34 pm - 11:55 pm
MSN
-
PDX
8h 21m
1 stop
$409United Airlines
Sat, May 16 - Wed, May 20

Delta flights from Portland to Madison

Our best Delta deals on Portland to Madison flight tickets
Delta
Jun 19
PDX12:40 amPortland
5h 40m
1 stop
MSN8:20 amMadison Truax Field
Jul 3
MSN6:15 amMadison Truax Field
6h 36m
1 stop
PDX10:51 amPortland
$397
Delta
Apr 21
PDX7:32 pmPortland
11h 29m
2 stops
MSN9:01 amMadison Truax Field
Apr 28
MSN6:00 amMadison Truax Field
10h 53m
2 stops
PDX2:53 pmPortland
$417
Delta
May 15
PDX1:35 pmPortland
5h 52m
1 stop
MSN9:27 pmMadison Truax Field
May 18
MSN6:30 amMadison Truax Field
6h 23m
1 stop
PDX10:53 amPortland
$418

United Airlines flights from Portland to Madison

Our best United Airlines deals on Portland to Madison flight tickets
United Airlines
Aug 12
PDX5:00 amPortland
6h 13m
1 stop
MSN1:13 pmMadison Truax Field
Aug 18
MSN10:49 amMadison Truax Field
8h 54m
2 stops
PDX5:43 pmPortland
$374
United Airlines
Jul 7
PDX11:40 pmPortland
8h 19m
1 stop
MSN9:59 amMadison Truax Field
Aug 8
MSN7:17 pmMadison Truax Field
6h 45m
1 stop
PDX12:02 amPortland
$390
United Airlines
May 2
PDX5:00 amPortland
8h 02m
2 stops
MSN3:02 pmMadison Truax Field
May 4
MSN5:34 pmMadison Truax Field
8h 21m
1 stop
PDX11:55 pmPortland
$392

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 March 18, 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

Tue 4/21

11:40 pm-11:05 am

1 stop9h 25m

Madison Truax Field

Tue 4/28

5:42 pm-10:56 pm

1 stop7h 14m

$349

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 6/6

12:35 pm-7:14 pm

1 stop28h 39m

Madison Truax Field

Sat 6/13

6:23 pm-11:13 am

1 stop18h 50m

$361

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 4/21

6:00 am-5:22 pm

1 stop9h 22m

Madison Truax Field

Sat 4/25

5:37 pm-11:57 pm

1 stop8h 20m

$369

PortlandMadison

PDX - MSN

PDXMSN

Portland

Wed 8/12

5:00 am-1:13 pm

1 stop6h 13m

Madison Truax Field

Tue 8/18

10:49 am-5:43 pm

2 stops8h 54m

$374

PortlandMadison

PDX - MSN

PDXMSN

Portland

Tue 7/7

11:40 pm-9:59 am

1 stop8h 19m

Madison Truax Field

Sat 8/8

7:17 pm-12:02 am

1 stop6h 45m

$390

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 5/2

5:00 am-3:02 pm

2 stops8h 02m

Madison Truax Field

Mon 5/4

5:34 pm-11:55 pm

1 stop8h 21m

$392
Quickest round-trip

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 6/19

12:40 am-8:20 am

1 stop5h 40m

Madison Truax Field

Sat 7/4

11:53 am-3:58 pm

1 stop6h 05m

$397

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 3/28

5:40 am-5:05 pm

1 stop9h 25m

Madison Truax Field

Wed 4/1

5:45 pm-12:34 am

1 stop8h 49m

$399

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 4/17

11:59 pm-8:57 am

1 stop6h 58m

Madison Truax Field

Mon 4/20

8:30 am-3:09 pm

1 stop8h 39m

$401

PortlandMadison

PDX - MSN

PDXMSN

Portland

Sat 5/16

2:41 pm-10:58 pm

1 stop6h 17m

Madison Truax Field

Wed 5/20

5:34 pm-11:55 pm

1 stop8h 21m

$409

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 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 September is your next best option. Flight prices from Portland to Madison during September average around $411.

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 $464 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.

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 March 2026, prices for Portland to Madison flights are approximately 67% 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

6h 27m

Direct flights

None
The fastest flight from Portland to Madison takes 6h 27m
There are no direct flights from Portland to Madison. There are no popular flight routes from Portland to Madison.
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 6h 27m, 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
5.7
3,025 reviews
Search Frontier flights
American AirlinesPriceFrom $283Free CancellationRating
7.1
11,468 reviews
Search American Airlines flights
DeltaPriceFrom $288Free CancellationRating
7.9
8,286 reviews
Search Delta flights
United AirlinesPriceFrom $298Free CancellationRating
7.4
9,435 reviews
Search United Airlines flights

Traveling to a place near Madison?

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

An easier way to manage your Madison trip

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