$159+ Cheap flights from Portland to Madison (PDX - 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Jul 6 — Jul 131
Round-trip
1 adult, Economy
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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 June 6, 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 June 6, 2026.
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Fri 7/33:31 pm
PDX
- MSN
1 stop6h 42m
American Airlines
Wed 7/86:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/2![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/6. 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 7/212:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sat 7/1112:03 pm
MSN
- PDX
1 stop7h 32m
Delta
Deal found 6/6![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 6/2. 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 9/911:39 am
PDX
- MSN
1 stop8h 18m
Delta
Sun 9/135:55 pm
MSN
- PDX
1 stop7h 39m
Delta
Deal found 6/2![Delta logo]()
$333
This American Airlines deal was found by Cheapflights users on 6/4. 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 7/411:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Thu 7/96:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/253:30 pm
PDX
- MSN
1 stop6h 49m
American Airlines
Sun 6/285:00 am
MSN
- PDX
1 stop7h 25m
American Airlines
Deal found 6/3![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/4. 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 9/712:10 pm
MSN
- PDX
1 stop7h 24m
Delta
Deal found 6/4![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/212:45 am
PDX
- MSN
1 stop7h 53m
American Airlines
Sat 7/118:00 am
MSN
- PDX
1 stop6h 49m
American Airlines
Deal found 6/3![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/1. 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 7/110:59 pm
PDX
- MSN
1 stop6h 52m
American Airlines
Mon 7/66:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/1![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 6/1. 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 6/2512:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sun 6/286:00 am
MSN
- PDX
1 stop6h 39m
Delta
Deal found 6/1![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 6/4. 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 6/253:30 pm
PDX
- MSN
1 stop6h 49m
American Airlines
Tue 6/305:00 am
MSN
- PDX
1 stop7h 25m
American Airlines
Deal found 6/4![American Airlines logo]()
$381
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 June 6, 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 June 6, 2026.
This United Airlines deal was found by Cheapflights users on 6/3. 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 7/911:40 pm
PDX
- MSN
1 stop8h 07m
United Airlines
Tue 7/145:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/3![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 6/1. 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 7/212:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sun 7/56:00 am
MSN
- PDX
1 stop6h 40m
Delta
Deal found 6/1![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 6/3. 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 7/411:00 am
PDX
- MSN
2 stops9h 32m
United Airlines
Sat 7/115:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/3![United Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 6/1. 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 9/911:10 am
PDX
- MSN
2 stops8h 47m
Delta
Sun 9/135:55 pm
MSN
- PDX
1 stop7h 39m
Delta
Deal found 6/1![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 6/1. 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 10/208:40 am
PDX
- MSN
2 stops11h 55m
United Airlines
Sat 10/246:49 am
MSN
- PDX
2 stops12h 49m
United Airlines
Deal found 6/1![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 6/1. 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 11/189:40 am
PDX
- MSN
2 stops11h 15m
Delta
Mon 11/237:55 pm
MSN
- PDX
1 stop5h 52m
Delta
Deal found 6/1![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 6/5. 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 9/55:00 am
PDX
- MSN
1 stop6h 13m
United Airlines
Wed 9/96:30 am
MSN
- PDX
1 stop6h 58m
United Airlines
Deal found 6/5![United Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 6/4. 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 7/310:40 pm
PDX
- MSN
1 stop7h 59m
United Airlines
Sun 7/55:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/4![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 6/3. 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.
Sat 7/1112:33 am
PDX
- MSN
1 stop5h 38m
Delta
Sat 7/186:00 am
MSN
- PDX
2 stops18h 38m
Delta
Deal found 6/3![Delta logo]()
$498
This Delta deal was found by Cheapflights users on 6/5. 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 6/2112:33 am
PDX
- MSN
1 stop5h 39m
Delta
Wed 7/12:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Deal found 6/5![Delta logo]()
$504
This United Airlines deal was found by Cheapflights users on 6/2. 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 7/1411:16 am
PDX
- MSN
2 stops9h 56m
United Airlines
Mon 7/205:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/2![United Airlines logo]()
$494
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated June 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated June 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/253:30 pm
PDX
- MSN
1 stop6h 49m
American Airlines
Sun 6/285:00 am
MSN
- PDX
1 stop7h 25m
American Airlines
Deal found 6/3![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/1. 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 6/2512:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sun 6/286:00 am
MSN
- PDX
1 stop6h 39m
Delta
Deal found 6/1![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 6/4. 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 6/253:30 pm
PDX
- MSN
1 stop6h 49m
American Airlines
Tue 6/305:00 am
MSN
- PDX
1 stop7h 25m
American Airlines
Deal found 6/4![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 6/1. 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 7/110:59 pm
PDX
- MSN
1 stop6h 52m
American Airlines
Mon 7/66:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/1![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 6/6. 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 7/212:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sat 7/1112:03 pm
MSN
- PDX
1 stop7h 32m
Delta
Deal found 6/6![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/212:45 am
PDX
- MSN
1 stop7h 53m
American Airlines
Sat 7/118:00 am
MSN
- PDX
1 stop6h 49m
American Airlines
Deal found 6/3![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/2. 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.
Fri 7/33:31 pm
PDX
- MSN
1 stop6h 42m
American Airlines
Wed 7/86:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/2![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 6/4. 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 7/411:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Thu 7/96:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 6/2. 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 7/1612:33 am
PDX
- MSN
1 stop5h 38m
Delta
Mon 7/202:00 pm
MSN
- PDX
1 stop9h 48m
Delta
Deal found 6/2![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Fri 7/1711:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Mon 7/206:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/3![American Airlines logo]()
$384
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 June 6, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated June 6, 2026.
This Delta deal was found by Cheapflights users on 6/2. 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 9/812:40 am
PDX
- MSN
1 stop5h 40m
Delta
Deal found 6/2![Delta logo]()
$159
This Booking.com deal was found by Cheapflights users on 6/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:26 pm
PDX
- MSN
1 stop28h 44m
Frontier
Deal found 6/2![Frontier logo]()
$181
This Booking.com deal was found by Cheapflights users on 6/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:26 pm
PDX
- MSN
1 stop28h 43m
Frontier
Deal found 6/4![Frontier logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/2. 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 7/14:15 pm
PDX
- MSN
1 stop5h 44m
United Airlines
Deal found 6/2![United Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 6/2. 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 8/912:30 am
PDX
- MSN
1 stop5h 46m
Delta
Deal found 6/2![Delta logo]()
$230
This Booking.com deal was found by Cheapflights users on 6/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:20 pm
PDX
- MSN
1 stop28h 50m
Frontier
Deal found 6/2![Frontier logo]()
$236
This United Airlines deal was found by Cheapflights users on 6/3. 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 7/1411:16 am
PDX
- MSN
2 stops9h 56m
United Airlines
Deal found 6/3![United Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 6/4. 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.
Sat 8/812:30 am
PDX
- MSN
1 stop5h 46m
Delta
Deal found 6/4![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 6/2. 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 7/411:00 am
PDX
- MSN
2 stops9h 32m
United Airlines
Deal found 6/2![United Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 6/2. 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 6/275:00 am
PDX
- MSN
1 stop7h 07m
United Airlines
Deal found 6/2![United Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/246:19 pm
PDX
- MSN
3 stops37h 28m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$325
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 June 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (American Airlines) |
One-way from | $159 (Delta) |
Popular in | March |
Cheapest in | February |
Average price | $478 |
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 2,558,603 searches. Data last updated June 6, 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 - MSN
PDXMSN
Portland
Thu 7/9
11:40 pm-9:47 am
1 stop8h 07m
Madison Truax Field
Tue 7/14
5:00 am-9:34 am
1 stop6h 34m
$335
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sat 7/4
11:00 am-10:32 pm
2 stops9h 32m
Madison Truax Field
Sat 7/11
5:00 am-9:34 am
1 stop6h 34m
$426
PortlandMadison
PDX - MSN
PDXMSN
Portland
Tue 10/20
8:40 am-10:35 pm
2 stops11h 55m
Madison Truax Field
Sat 10/24
6:49 am-5:38 pm
2 stops12h 49m
$431
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sat 9/5
5:00 am-1:13 pm
1 stop6h 13m
Madison Truax Field
Wed 9/9
6:30 am-11:28 am
1 stop6h 58m
$440
Quickest round-trip
PortlandMadison
PDX - MSN
PDXMSN
Portland
Thu 7/2
12:33 am-8:12 am
1 stop5h 39m
Madison Truax Field
Sun 7/5
6:00 am-10:40 am
1 stop6h 40m
$444
PortlandMadison
PDX - MSN
PDXMSN
Portland
Fri 7/3
10:40 pm-8:39 am
1 stop7h 59m
Madison Truax Field
Sun 7/5
5:00 am-9:34 am
1 stop6h 34m
$449
PortlandMadison
PDX - MSN
PDXMSN
Portland
Wed 9/9
11:10 am-9:57 pm
2 stops8h 47m
Madison Truax Field
Sun 9/13
5:55 pm-11:34 pm
1 stop7h 39m
$452
PortlandMadison
PDX - MSN
PDXMSN
Portland
Wed 11/18
9:40 am-10:55 pm
2 stops11h 15m
Madison Truax Field
Mon 11/23
7:55 pm-11:47 pm
1 stop5h 52m
$452
PortlandMadison
PDX - MSN
PDXMSN
Portland
Tue 7/14
11:16 am-11:12 pm
2 stops9h 56m
Madison Truax Field
Mon 7/20
5:00 am-9:34 am
1 stop6h 34m
$494
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sat 7/11
12:33 am-8:11 am
1 stop5h 38m
Madison Truax Field
Sat 7/18
6:00 am-10:38 pm
2 stops18h 38m
$498
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 June.
| 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 8 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 $398). Flying from Portland to Madison in March is currently the most expensive (average of $581). 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?
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 June 6, 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.
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Entertainment
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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 locationsPortage
Sun Prairie
Middleton
Baraboo
Fitchburg
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Complete your trip
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Search flights from Portland to Madison by cabin class
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Other flights to Madison
Explore flights to Madison departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 6, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on June 6, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on June 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Portland to Madison
Discover the top 5 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 2,558,603 searches. Data last updated June 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$288 | Average$472 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$288 | Average$492 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$463 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$630 | FlexibilityNo cancel fee | On-time75% |