$202+ Cheap flights from Portland to Madison (PDX - MSN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Madison with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Portland to MadisonExplore the most affordable flight options available from Portland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Portland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/95:00 am -
1 stop10h 00m
Sat 12/126:40 am -
1 stop9h 01m
Deal found 10/20![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/91:15 pm -
1 stop5h 54m
Sun 12/135:00 am -
1 stop8h 42m
Deal found 10/20![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/95:00 am -
1 stop6h 24m
Sat 12/1212:35 pm -
2 stops10h 40m
Deal found 10/20![United Airlines logo]()
$376
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:34 pm -
1 stop6h 33m
Sun 11/223:00 pm -
1 stop9h 27m
Deal found 10/21![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:26 pm -
1 stop5h 57m
Sat 12/126:30 am -
2 stops8h 46m
Deal found 10/22![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 12/102:26 pm -
1 stop5h 57m
Sun 12/136:30 am -
2 stops8h 46m
Deal found 10/20![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:35 am -
1 stop7h 34m
Sun 11/227:49 pm -
1 stop5h 57m
Deal found 10/22![Delta logo]()
$395
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/3112:49 pm -
1 stop5h 49m
Mon 1/45:00 am -
1 stop8h 47m
Deal found 10/22![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:58 am -
1 stop7h 19m
Mon 11/232:00 pm -
1 stop10h 10m
Deal found 10/22![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:15 pm -
2 stops7h 52m
Sat 11/215:45 pm -
1 stop7h 24m
Deal found 10/21![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:51 am -
1 stop5h 15m
Wed 11/117:49 pm -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Tue 11/171:15 pm -
1 stop5h 28m
Tue 12/15:30 am -
1 stop8h 11m
Deal found 10/24![United Airlines logo]()
$422
Best flights from Portland to MadisonDiscover carefully curated flight deals from Portland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Portland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:00 am -
1 stop6h 24m
Tue 12/1510:42 am -
1 stop10h 01m
Deal found 10/22![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:35 am -
1 stop7h 44m
Sat 11/217:49 pm -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/610:46 am -
1 stop7h 02m
Tue 1/128:53 am -
1 stop6h 34m
Deal found 10/23![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1512:35 am -
1 stop7h 44m
Sun 11/226:30 am -
1 stop6h 14m
Deal found 10/22![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/91:15 pm -
1 stop5h 54m
Sun 12/135:00 am -
1 stop8h 42m
Deal found 10/20![United Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:35 am -
1 stop7h 44m
Sun 11/227:49 pm -
1 stop5h 57m
Deal found 10/22![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/95:00 am -
1 stop6h 24m
Sat 12/1212:35 pm -
2 stops10h 40m
Deal found 10/20![United Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:51 am -
1 stop5h 15m
Wed 11/117:49 pm -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Mon 11/162:34 pm -
1 stop6h 33m
Sun 11/225:45 pm -
1 stop7h 24m
Deal found 10/20![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/192:34 pm -
1 stop6h 33m
Thu 11/268:15 am -
1 stop9h 08m
Deal found 10/20![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 12/102:26 pm -
1 stop5h 57m
Sun 12/136:30 am -
2 stops8h 46m
Deal found 10/20![United Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:34 pm -
1 stop6h 33m
Sun 11/223:52 pm -
2 stops9h 17m
Deal found 10/22![United Airlines logo]()
$464
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:02 am -
1 stop6h 02m
Tue 10/272:38 pm -
1 stop8h 35m
Deal found 10/22![United Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:51 am -
1 stop5h 15m
Wed 11/117:49 pm -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:44 pm -
1 stop5h 39m
Tue 11/107:49 pm -
1 stop5h 57m
Deal found 10/21![Delta logo]()
$449
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 11/146:00 am -
1 stop9h 07m
Sat 11/215:37 pm -
1 stop8h 39m
Deal found 10/21![American Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:15 pm -
2 stops7h 52m
Sat 11/215:45 pm -
1 stop7h 24m
Deal found 10/21![United Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:34 pm -
1 stop6h 33m
Sun 11/223:00 pm -
1 stop9h 27m
Deal found 10/21![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/24. 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.
Tue 11/171:15 pm -
1 stop5h 28m
Tue 12/15:30 am -
1 stop8h 11m
Deal found 10/24![United Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:58 am -
1 stop7h 19m
Mon 11/232:00 pm -
1 stop10h 10m
Deal found 10/22![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/192:34 pm -
1 stop6h 33m
Thu 11/268:15 am -
2 stops14h 00m
Deal found 10/20![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:35 am -
1 stop7h 34m
Sun 11/227:49 pm -
1 stop5h 57m
Deal found 10/22![Delta logo]()
$395
One-way flights from Portland to MadisonSearch for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/119:31 pm -
3 stops34h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:58 pm -
2 stops42h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$207
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:52 pm -
2 stops21h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Wed 12/2311:59 pm -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/124:29 pm -
3 stops46h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/128:40 am -
2 stops9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$308
This Mytrip deal was found by Cheapflights users on 10/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:23 am -
2 stops24h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Multiple Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:20 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2412:49 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$318
Find flight deals from Portland to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (American Airlines) |
One-way from | $202 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $584 |
Cheapflights 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, Cheapflights users made 7,457,451 searches. Data last updated October 25, 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
Cheapest round-trip
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Mon 1/11
9:31 pm-9:58 am
3 stops34h 27m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$202
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Sun 11/22
11:23 am-1:36 pm
2 stops24h 13m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$310
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Wed 11/25
1:56 pm-9:17 pm
1 stop5h 21m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Mon 1/11
7:10 am-3:06 pm
1 stop5h 56m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$323
Quickest round-trip
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Fri 12/4
11:59 am-7:16 pm
1 stop5h 17m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$323
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Thu 11/26
11:10 pm-3:11 pm
2 stops14h 01m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$358
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Wed 11/25
1:15 pm-11:07 pm
2 stops7h 52m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$368
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Sat 12/12
5:00 am-1:24 pm
1 stop6h 24m
Madison Truax Field
Tue 12/15
10:42 am-6:43 pm
1 stop10h 01m
$371
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
Wed 11/18
12:35 am-10:19 am
1 stop7h 44m
Madison Truax Field
Sat 11/21
7:49 pm-11:46 pm
1 stop5h 57m
$375
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Portland to Madison
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Madison in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Madison flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Portland with our price prediction graph.
PDX-MSN
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 Portland to Madison
How far ahead should I book a flight from Portland to Madison?
The price you pay for your flight from Portland to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 74 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Portland to Madison?
Currently, February is the cheapest month in which you can book a flight from Portland to Madison (average of $416). Flying from Portland to Madison in December is currently the most expensive (average of $637). 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 Portland to Madison?
Airfare is below average for this route at the moment.
Portland to Madison flights typically cost between $418 and $717 in December.The cheapest round-trip price found within the last 5 days was $371 on American Airlines (Dec 9-Dec 12).
Reviews of airlines servicing Madison
Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated October 25, 2026.
See what other customers who have flown with Alaska Airlines,Delta, andUnited Airlines from Portland to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Related info for your journey
Find useful and relevant information for your journey from Portland to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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Top 4 airlines flying from Portland to Madison
Discover the top 4 airlines that operate flights from Portland 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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$308 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$630 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$335 | Average$530 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$344 | Average$487 | FlexibilityNo cancel fee | On-timeN/A |