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Madison

$161+ Cheap flights from Oregon to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Aug 25 — Sep 11
Tue 8/25
Tue 9/1
1 adult, Economy
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Cheap flight deals from Oregon to Madison

Cheapest flights from Oregon to Madison
Explore the most affordable flight options available from Oregon to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 26, 2026.

This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:15 pm
PDX
-
MSN
1 stop5h 28m
United Airlines
Sat 11/73:08 pm
MSN
-
PDX
1 stop8h 05m
United Airlines
Deal found 7/25$326
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:03 pm
BOI
-
MSN
1 stop6h 08m
American Airlines
Tue 11/102:56 pm
MSN
-
BOI
1 stop9h 01m
American Airlines
Deal found 7/21$329
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:09 pm
PDX
-
MSN
1 stop7h 05m
American Airlines
Sat 9/192:40 pm
MSN
-
PDX
1 stop7h 50m
American Airlines
Deal found 7/26$331
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:27 pm
BOI
-
MSN
1 stop8h 45m
American Airlines
Wed 11/117:05 am
MSN
-
BOI
2 stops13h 19m
American Airlines
Deal found 7/21$334
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:34 pm
PDX
-
MSN
1 stop7h 43m
American Airlines
Tue 9/85:46 pm
MSN
-
PDX
1 stop7h 23m
American Airlines
Deal found 7/22$335
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:19 pm
BOI
-
MSN
1 stop7h 51m
American Airlines
Wed 8/267:54 am
MSN
-
BOI
1 stop6h 30m
American Airlines
Deal found 7/26$339
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:27 pm
PDX
-
MSN
1 stop6h 08m
United Airlines
Tue 10/205:10 am
MSN
-
PDX
2 stops8h 55m
United Airlines
Deal found 7/25$343
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:08 pm
PDX
-
MSN
1 stop7h 06m
American Airlines
Sun 9/135:00 am
MSN
-
PDX
1 stop7h 55m
American Airlines
Deal found 7/26$345
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:00 am
MFR
-
MSN
1 stop7h 00m
American Airlines
Fri 9/252:40 pm
MSN
-
MFR
1 stop6h 31m
American Airlines
Deal found 7/22$349
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:07 pm
PDX
-
MSN
1 stop5h 52m
United Airlines
Wed 8/265:00 am
MSN
-
PDX
2 stops9h 00m
United Airlines
Deal found 7/24$350
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:00 pm
BOI
-
MSN
1 stop4h 55m
Delta
Tue 10/277:46 pm
MSN
-
BOI
1 stop5h 13m
Delta
Deal found 7/25$353
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:20 pm
PDX
-
MSN
1 stop7h 32m
Delta
Mon 9/76:05 am
MSN
-
PDX
1 stop6h 36m
Delta
Deal found 7/23$359

Find flight deals from Oregon to Madison

Keep the following information in mind while searching for Oregon to Madison flight deals. Data was last updated July 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$321
(United Airlines)

One-way from

$161
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$536
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Madison Truax Field flights.
Search Deals
From Oregon to Madison Truax Field
Search Deals
One-way flight from Oregon to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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, Cheapflights users made 2,558,603 searches. Data last updated July 26, 2026.
Use the filters below to find and compare flights from Oregon to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Wed 9/30

3:21 pm-12:17 am

1 stop7h 56m

Madison Truax Field

Sun 10/4

7:15 am-2:31 pm

1 stop8h 16m

$339

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Mon 8/31

6:30 am-1:13 pm

1 stop5h 43m

Madison Truax Field

Sun 9/6

2:44 pm-10:53 pm

1 stop9h 09m

$339

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Wed 11/4

8:00 am-6:20 pm

2 stops9h 20m

Madison Truax Field

Wed 11/11

7:05 am-7:24 pm

2 stops13h 19m

$339

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 9/25

2:27 pm-10:35 pm

1 stop6h 08m

Madison Truax Field

Wed 9/30

5:00 am-9:31 am

1 stop6h 31m

$345

PortlandMadison

PDX - MSN

PDXMSN

Portland

Fri 9/25

2:27 pm-10:35 pm

1 stop6h 08m

Madison Truax Field

Wed 10/7

5:00 am-9:31 am

1 stop6h 31m

$345

MedfordMadison

MFR - MSN

MFRMSN

Medford

Sun 9/13

5:00 am-2:00 pm

1 stop7h 00m

Madison Truax Field

Fri 9/25

2:40 pm-7:11 pm

1 stop6h 31m

$349

EugeneMadison

EUG - MSN

EUGMSN

Eugene

Sat 9/5

2:19 pm-10:51 pm

1 stop6h 32m

Madison Truax Field

Tue 9/8

8:05 am-1:10 pm

1 stop7h 05m

$359

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Tue 9/22

6:30 am-2:00 pm

1 stop6h 30m

Madison Truax Field

Mon 9/28

7:17 am-1:00 pm

1 stop6h 43m

$364

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Mon 8/10

3:19 pm-12:10 am

1 stop7h 51m

Madison Truax Field

Wed 8/26

7:05 am-4:49 pm

2 stops10h 44m

$369

BoiseMadison

BOI - MSN

BOIMSN

Boise Air Term. Gowen Fld

Wed 9/23

3:21 pm-12:17 am

1 stop7h 56m

Madison Truax Field

Mon 9/28

7:15 am-2:31 pm

1 stop8h 16m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 53 resultsSorted by cheapest first
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Best time to book a flight from Oregon to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Oregon with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Madison

What is the cheapest month to book a flight from Oregon to Madison?

Currently, February is the cheapest month in which you can book a flight from Oregon to Madison (average of $400). Flying from Oregon to Madison in May is currently the most expensive (average of $591). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Oregon to Madison?

Airfare is below average for this route at the moment.
Oregon to Madison flights typically cost between $392 and $542 in October.
The cheapest round-trip price found within the last 5 days was $321 on United Airlines (Oct 21-Oct 24).

How far ahead should I book a flight from Oregon to Madison?

Booking 68 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oregon to Madison. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from Oregon?

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly into when you book flights from Oregon to Madison.

  • How long is the flight from Oregon to Madison?

    Departing from Oregon to Madison will take you 5h 20m. Airlines will cover a distance of 1639 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Oregon to Madison one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $161. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Oregon to Madison for a low price.

  • What are the most popular routes from Oregon to Madison?

    The most popular route from Oregon to Madison is Portland - Madison Truax Field. You may also consider Boise Air Term. Gowen Fld - Madison Truax Field or Eugene - Madison Truax Field.

  • Can I find deals for flights from Oregon to Madison that include hotel bookings?

    Yes. In addition to deals on Oregon to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Madison.

  • Can I find deals for business class flights from Oregon to Madison?

    Yes. Cheapflights offers flight deals from Oregon to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oregon to Madison?

    Currently, February is the cheapest month in which you can book a flight from Oregon to Madison (average of $400). Flying from Oregon to Madison in May is currently the most expensive (average of $591). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

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

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Alternative routes for Oregon to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oregon to Madison

Discover the top 4 airlines that operate flights from Oregon to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$308Average$472FlexibilityNo cancel feeOn-time69%
DeltaCheapest$313Average$507FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$317Average$630FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$334Average$553FlexibilityNo cancel feeOn-time71%

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