$254+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Oct 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Madison with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Madison
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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 September 9, 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 September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:20 am -
1 stop9h 53m
Sat 10/176:46 am -
1 stop7h 36m
Deal found 9/6![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 9/7. 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 11/1411:49 pm -
1 stop9h 03m
Sun 11/152:52 pm -
1 stop10h 18m
Deal found 9/7![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 10/1110:55 pm -
1 stop7h 16m
Tue 10/208:00 am -
1 stop7h 39m
Deal found 9/4![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 9/7. 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 10/131:44 pm -
1 stop5h 11m
Wed 10/216:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/271:15 pm -
1 stop5h 28m
Sat 11/76:25 am -
2 stops10h 12m
Deal found 9/4![United Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
1 stop6h 02m
Sat 10/175:10 am -
2 stops9h 00m
Deal found 9/6![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 9/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:49 pm -
1 stop9h 03m
Thu 11/197:00 am -
1 stop8h 33m
Deal found 9/5![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/1211:12 pm -
1 stop7h 35m
Sat 10/246:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/8. 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 12/32:34 pm -
1 stop6h 29m
Tue 12/89:12 am -
2 stops10h 26m
Deal found 9/8![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/1211:12 pm -
1 stop7h 35m
Fri 10/237:46 pm -
1 stop5h 58m
Deal found 9/7![Delta logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/305:00 am -
1 stop6h 18m
Sat 10/35:10 am -
2 stops9h 00m
Deal found 9/8![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 9/7. 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 10/133:22 pm -
1 stop5h 35m
Sun 10/256:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$385
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 September 9, 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 September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/271:15 pm -
1 stop5h 28m
Sat 11/76:25 am -
2 stops10h 12m
Deal found 9/4![United Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 9/8. 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 12/311:53 am -
1 stop7h 37m
Wed 12/96:32 am -
1 stop8h 16m
Deal found 9/8![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
1 stop6h 02m
Sat 10/175:10 am -
2 stops9h 00m
Deal found 9/6![United Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 9/8. 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 12/32:34 pm -
1 stop6h 29m
Tue 12/89:12 am -
2 stops10h 26m
Deal found 9/8![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 9/7. 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 11/135:50 pm -
2 stops18h 10m
Mon 11/167:49 pm -
1 stop5h 57m
Deal found 9/7![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 9/7. 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 11/147:00 am -
2 stops12h 13m
Mon 11/167:49 pm -
1 stop5h 57m
Deal found 9/7![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 9/8. 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 1/95:15 am -
1 stop6h 35m
Tue 1/123:09 pm -
1 stop7h 40m
Deal found 9/8![United Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 9/8. 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 12/37:21 pm -
2 stops11h 16m
Wed 12/99:12 am -
1 stop8h 14m
Deal found 9/8![United Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/3010:43 am -
2 stops9h 52m
Sat 10/36:42 am -
2 stops9h 45m
Deal found 9/8![United Airlines logo]()
$489
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated September 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/7. 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 9/2611:08 pm -
1 stop7h 06m
Sat 10/35:00 am -
1 stop7h 55m
Deal found 9/7![American Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/3011:08 pm -
1 stop7h 06m
Sat 10/312:56 pm -
1 stop8h 40m
Deal found 9/8![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/305:00 am -
1 stop6h 18m
Sat 10/35:10 am -
2 stops9h 00m
Deal found 9/8![United Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 9/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:10 am -
1 stop6h 47m
Sat 10/107:05 pm -
1 stop6h 54m
Deal found 9/6![American Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:20 am -
1 stop9h 53m
Sat 10/176:46 am -
1 stop7h 36m
Deal found 9/6![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
1 stop6h 02m
Sat 10/175:10 am -
2 stops9h 00m
Deal found 9/6![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 10/1110:55 pm -
1 stop7h 16m
Tue 10/208:00 am -
1 stop7h 39m
Deal found 9/4![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/1211:12 pm -
1 stop7h 35m
Sat 10/246:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/1211:12 pm -
1 stop7h 35m
Fri 10/237:46 pm -
1 stop5h 58m
Deal found 9/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 9/7. 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 10/131:44 pm -
1 stop5h 11m
Wed 10/216:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 9/7. 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 10/133:22 pm -
1 stop5h 35m
Sun 10/256:00 am -
1 stop6h 34m
Deal found 9/7![Delta logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/271:15 pm -
1 stop5h 28m
Sat 11/76:25 am -
2 stops10h 12m
Deal found 9/4![United Airlines logo]()
$352
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 September 9, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sat 9/1912:24 pm -
2 stops26h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Fri 9/1812:38 pm -
2 stops19h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:39 pm -
3 stops43h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1212:25 pm -
2 stops19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 9/7. 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 10/73:22 pm -
1 stop5h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 12/34:35 pm -
2 stops39h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/105:20 am -
1 stop9h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 9/7. 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 10/911:51 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1311:49 am -
2 stops20h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/7. 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 10/1010:43 am -
2 stops9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (American Airlines) |
One-way from | $254 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $430 |
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 September 9, 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 9/28
12:39 pm-9:53 am
3 stops43h 14m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$281
Quickest round-trip
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Wed 10/7
3:22 pm-10:57 pm
1 stop5h 35m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$293
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Thu 10/29
10:55 pm-8:11 am
1 stop7h 16m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$303
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Mon 10/12
11:43 am-9:01 pm
1 stop7h 18m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Fri 10/2
12:38 pm-9:58 am
2 stops19h 20m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$330
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Tue 10/27
1:15 pm-8:43 pm
1 stop5h 28m
Madison Truax Field
Sat 11/7
6:25 am-2:37 pm
2 stops10h 12m
$352
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Sat 10/10
7:02 am-3:04 pm
1 stop6h 02m
Madison Truax Field
Sat 10/17
5:10 am-12:10 pm
2 stops9h 00m
$356
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Fri 9/25
7:00 am-5:11 pm
1 stop8h 11m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$360
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Thu 12/3
11:53 am-9:30 pm
1 stop7h 37m
Madison Truax Field
Wed 12/9
6:32 am-12:48 pm
1 stop8h 16m
$365
PortlandMadison
PDX Portland - MSN Madison Truax Field
PDXMSN
Portland
Fri 10/9
10:33 pm-1:37 pm
2 stops13h 04m
Madison Truax Field
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$368
Showing 1-10 of 20 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 September.
| 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 $399). 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 $358 and $493 in October.The cheapest round-trip price found within the last 5 days was $331 on American Airlines (Oct 10-Oct 17).
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 September 9, 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.
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Food
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
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 September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$309 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$630 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$335 | Average$514 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$489 | FlexibilityNo cancel fee | On-timeN/A |