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Cheap flights from Portland to Madison from $195

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.
United Airlines Logo
10:46 am - 7:48 pmPDX  Portland-MSN Madison Truax Field
7h 02m1 stop Chicago O'Hare Intl
United Airlines Logo
8:53 am - 1:27 pmMSN  Madison Truax Field-PDX Portland
6h 34m1 stop Denver Intl
$371United Airlines
Wed, Jan 6 - Tue, Jan 12
American Airlines Logo
11:13 pm - 8:14 amPDX  Portland-MSN Madison Truax Field
7h 01m1 stop Chicago O'Hare Intl
American Airlines Logo
7:15 am - 1:12 pmMSN  Madison Truax Field-PDX Portland
7h 57m1 stop Phoenix Sky Harbor Intl
$375American Airlines
Fri, Dec 11 - Tue, Dec 15
Delta Logo
6:00 am - 2:10 pmPDX  Portland-MSN Madison Truax Field
6h 10m1 stop Minneapolis St Paul
Delta Logo
6:32 am - 10:48 amMSN  Madison Truax Field-PDX Portland
6h 16m1 stop Minneapolis St Paul
$375Delta
Wed, Dec 2 - Wed, Dec 9
United Airlines Logo
7:00 am - 2:50 pmPDX  Portland-MSN Madison Truax Field
5h 50m1 stop Chicago O'Hare Intl
United Airlines Logo
5:30 am - 11:41 amMSN  Madison Truax Field-PDX Portland
8h 11m1 stop Chicago O'Hare Intl
$375United Airlines
Wed, Dec 2 - Wed, Dec 9
Delta Logo
11:59 am - 7:16 pmPDX  Portland-MSN Madison Truax Field
5h 17m1 stop Minneapolis St Paul
Delta Logo
2:50 pm - 8:24 pmMSN  Madison Truax Field-PDX Portland
7h 34m1 stop Minneapolis St Paul
$379Delta
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
11:13 pm - 8:14 amPDX  Portland-MSN Madison Truax Field
7h 01m1 stop Chicago O'Hare Intl
American Airlines Logo
7:15 am - 1:35 pmMSN  Madison Truax Field-PDX Portland
8h 20m1 stop Phoenix Sky Harbor Intl
$399American Airlines
Thu, Dec 10 - Mon, Dec 14
Alaska Airlines Logo
8:30 am - 8:15 pmPDX  Portland-MSN Madison Truax Field
9h 45m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
9:43 am - 8:50 pmMSN  Madison Truax Field-PDX Portland
13h 07m2 stops Chicago O'Hare Intl San Diego
$515Alaska Airlines
Fri, Dec 11 - Tue, Dec 15
Alaska Airlines Logo
9:30 pm - 8:14 amPDX  Portland-MSN Madison Truax Field
8h 44m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
11:49 am - 5:05 pmMSN  Madison Truax Field-PDX Portland
7h 16m1 stop Chicago O'Hare Intl
$519Alaska Airlines
Fri, Dec 4 - Sat, Dec 5
Multiple Airlines Logo
1:04 pm - 2:01 pmPDX  Portland-MSN Madison Truax Field
22h 57m2 stops Denver Intl Phoenix Sky Harbor Intl
Multiple Airlines Logo
2:40 pm - 9:21 pmMSN  Madison Truax Field-PDX Portland
32h 41m3 stops Phoenix Sky Harbor Intl Salt Lake City Las Vegas Harry Reid Intl
$695Multiple Airlines
Thu, Dec 24 - Fri, Jan 1
Multiple Airlines Logo
1:04 pm - 2:01 pmPDX  Portland-MSN Madison Truax Field
22h 57m2 stops Denver Intl Phoenix Sky Harbor Intl
Multiple Airlines Logo
2:15 pm - 9:33 pmMSN  Madison Truax Field-PDX Portland
33h 18m3 stops Phoenix Sky Harbor Intl Denver Intl Las Vegas Harry Reid Intl
$875Multiple Airlines
Thu, Dec 24 - Mon, Dec 28

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United Airlines flights from Portland to Madison

Our best United Airlines deals on Portland to Madison flight tickets
United Airlines
Jan 6
PDX10:46 amPortland
7h 02m
1 stop
MSN7:48 pmMadison Truax Field
Jan 12
MSN8:53 amMadison Truax Field
6h 34m
1 stop
PDX1:27 pmPortland
$371
United Airlines
Dec 2
PDX7:00 amPortland
5h 50m
1 stop
MSN2:50 pmMadison Truax Field
Dec 9
MSN5:30 amMadison Truax Field
8h 11m
1 stop
PDX11:41 amPortland
$375
United Airlines
Jan 6
PDX5:00 amPortland
6h 28m
1 stop
MSN1:28 pmMadison Truax Field
Jan 12
MSN6:05 amMadison Truax Field
9h 22m
2 stops
PDX1:27 pmPortland
$376

American Airlines flights from Portland to Madison

Our best American Airlines deals on Portland to Madison flight tickets
American Airlines
Dec 25
PDX6:19 amPortland
8h 46m
1 stop
MSN5:05 pmMadison Truax Field
Dec 31
MSN5:45 pmMadison Truax Field
8h 01m
1 stop
PDX11:46 pmPortland
$424
American Airlines
Nov 18
PDX11:57 amPortland
7h 33m
1 stop
MSN9:30 pmMadison Truax Field
Dec 12
MSN5:51 amMadison Truax Field
8h 46m
1 stop
PDX12:37 pmPortland
$427
American Airlines
Nov 19
PDX12:00 pmPortland
7h 40m
1 stop
MSN9:40 pmMadison Truax Field
Nov 23
MSN11:22 amMadison Truax Field
10h 29m
1 stop
PDX7:51 pmPortland
$459

momondo Fare Finder

 
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

Wed 1/6

10:46 am-7:48 pm

1 stop7h 02m

Madison Truax Field

Tue 1/12

8:53 am-1:27 pm

1 stop6h 34m

$371

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Fri 12/11

11:13 pm-8:14 am

1 stop7h 01m

Madison Truax Field

Tue 12/15

7:15 am-1:12 pm

1 stop7h 57m

$375
Quickest round-trip

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 12/2

6:00 am-2:10 pm

1 stop6h 10m

Madison Truax Field

Wed 12/9

6:32 am-10:48 am

1 stop6h 16m

$375

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Wed 12/2

7:00 am-2:50 pm

1 stop5h 50m

Madison Truax Field

Wed 12/9

5:30 am-11:41 am

1 stop8h 11m

$375

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 12/3

11:59 am-7:16 pm

1 stop5h 17m

Madison Truax Field

Mon 12/7

2:50 pm-8:24 pm

1 stop7h 34m

$379

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 12/10

11:13 pm-8:14 am

1 stop7h 01m

Madison Truax Field

Mon 12/14

7:15 am-1:35 pm

1 stop8h 20m

$399

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Fri 12/11

8:30 am-8:15 pm

2 stops9h 45m

Madison Truax Field

Tue 12/15

9:43 am-8:50 pm

2 stops13h 07m

$515

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Fri 12/4

9:30 pm-8:14 am

2 stops8h 44m

Madison Truax Field

Sat 12/5

11:49 am-5:05 pm

1 stop7h 16m

$519

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 12/24

1:04 pm-2:01 pm

2 stops22h 57m

Madison Truax Field

Fri 1/1

2:40 pm-9:21 pm

3 stops32h 41m

$695

PortlandMadison

PDX Portland - MSN Madison Truax Field

PDXMSN

Portland

Thu 12/24

1:04 pm-2:01 pm

2 stops22h 57m

Madison Truax Field

Mon 12/28

2:15 pm-9:33 pm

3 stops33h 18m

$875

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 $378 to $681.
The lowest price recently found on this route was $371.

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 $511 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 32% 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 November 2026, prices for Portland to Madison flights are approximately 84% 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

$195

Fastest flight time

5h 57m

Direct flights

None
The best one-way flight to Madison from Portland in the past 72 hours is $195. The best round-trip flight deal from Portland to Madison found on momondo in the last 72 hours is $371.
The fastest flight from Portland to Madison takes 5h 57m
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 57m, 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
7.3
10,473 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $317Free CancellationRating
7.9
13,147 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $335Free CancellationRating
7.0
12,230 reviews
Search American Airlines flights
DeltaPriceFrom $344Free CancellationRating
7.8
8,701 reviews
Search Delta flights

  • United Airlines Flights From Portland to Madison

    United Airlines flies from Portland to Madison around 2 times per week, with 10,473 momondo users rating the airline 7.3/10. The cheapest United Airlines deal from Portland to Madison in the last 72 hours was $309 (round-trip), much lower than the average airfare cost of $474 for United Airlines flights on this route.

Traveling to a place near Madison?

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