$166+ Cheap flights from Madison to Portland (MSN - PDX)
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Cheapest flights from Madison to PortlandExplore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
Explore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 7/12:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Tue 7/712:33 am
PDX
- MSN
1 stop5h 38m
Delta
Deal found 6/8![Delta logo]()
$321
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.
Tue 9/16:05 am
MSN
- PDX
1 stop6h 41m
Delta
Mon 9/712:40 am
PDX
- MSN
1 stop5h 40m
Delta
Deal found 6/5![Delta logo]()
$331
This CheapOair deal was found by Cheapflights users on 6/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:55 pm
MSN
- PDX
1 stop22h 56m
Frontier
Wed 8/195:42 pm
PDX
- MSN
1 stop23h 27m
Frontier
Deal found 6/9![Frontier logo]()
$334
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.
Wed 7/156:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Tue 7/2111:41 pm
PDX
- MSN
1 stop8h 57m
American Airlines
Deal found 6/4![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/8. 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 9/26:53 pm
MSN
- PDX
1 stop7h 06m
American Airlines
Thu 9/1012:01 pm
PDX
- MSN
1 stop8h 56m
American Airlines
Deal found 6/8![American Airlines logo]()
$340
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.
Sat 7/1112:03 pm
MSN
- PDX
1 stop7h 32m
Delta
Sun 7/1912:33 am
PDX
- MSN
1 stop5h 38m
Delta
Deal found 6/5![Delta logo]()
$345
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.
Mon 8/106:53 pm
MSN
- PDX
1 stop7h 06m
American Airlines
Mon 8/1711:34 pm
PDX
- MSN
1 stop7h 43m
American Airlines
Deal found 6/4![American Airlines logo]()
$349
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:55 pm
MSN
- PDX
1 stop22h 56m
Frontier
Sat 8/2212:26 pm
PDX
- MSN
1 stop28h 43m
Frontier
Deal found 6/8![Frontier logo]()
$354
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/296:00 am
MSN
- PDX
1 stop8h 40m
Delta
Fri 7/312:33 am
PDX
- MSN
1 stop7h 39m
Delta
Deal found 6/8![Delta logo]()
$359
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 7/22:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Wed 7/83:00 pm
PDX
- MSN
1 stop6h 00m
Delta
Deal found 6/4![Delta logo]()
$364
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:00 am
MSN
- PDX
1 stop6h 55m
American Airlines
Wed 7/811:41 pm
PDX
- MSN
1 stop8h 57m
American Airlines
Deal found 6/5![American Airlines logo]()
$367
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:55 pm
MSN
- PDX
1 stop22h 56m
Frontier
Sat 8/2212:26 pm
PDX
- MSN
1 stop28h 43m
Frontier
Deal found 6/8![Frontier logo]()
$374
Best flights from Madison to PortlandDiscover carefully curated flight deals from Madison to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Madison to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 7/26:00 am
MSN
- PDX
1 stop6h 40m
Delta
Sun 7/512:33 am
PDX
- MSN
1 stop5h 39m
Delta
Deal found 6/8![Delta logo]()
$359
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:44 pm
MSN
- PDX
1 stop6h 34m
United Airlines
Tue 9/2910:43 am
PDX
- MSN
2 stops9h 52m
United Airlines
Deal found 6/6![United Airlines logo]()
$426
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 7/22:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Wed 7/83:00 pm
PDX
- MSN
1 stop6h 00m
Delta
Deal found 6/4![Delta logo]()
$364
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.
Sun 6/215:00 am
MSN
- PDX
1 stop6h 48m
United Airlines
Tue 6/3010:40 pm
PDX
- MSN
1 stop9h 19m
United Airlines
Deal found 6/4![United Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 6/272:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Sun 6/2812:33 am
PDX
- MSN
1 stop5h 39m
Delta
Deal found 6/8![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Fri 10/162:49 pm
MSN
- PDX
2 stops10h 08m
United Airlines
Sat 10/2412:45 pm
PDX
- MSN
1 stop6h 22m
United Airlines
Deal found 6/7![United Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 10/207:55 pm
MSN
- PDX
1 stop5h 52m
Delta
Sun 10/257:40 pm
PDX
- MSN
2 stops12h 35m
Delta
Deal found 6/8![Delta logo]()
$463
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.
Mon 8/35:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Tue 8/117:00 am
PDX
- MSN
2 stops11h 53m
United Airlines
Deal found 6/4![United Airlines logo]()
$534
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.
Fri 8/216:05 am
MSN
- PDX
1 stop6h 41m
Delta
Mon 8/318:44 pm
PDX
- MSN
2 stops9h 32m
Delta
Deal found 6/4![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Fri 8/213:55 pm
MSN
- PDX
1 stop8h 57m
United Airlines
Sun 8/235:00 am
PDX
- MSN
1 stop6h 13m
United Airlines
Deal found 6/7![United Airlines logo]()
$539
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.
Tue 9/86:15 am
MSN
- PDX
2 stops10h 51m
Delta
Fri 9/188:44 pm
PDX
- MSN
2 stops9h 38m
Delta
Deal found 6/5![Delta logo]()
$530
Last-minute flights from Madison to PortlandDiscover last-minute flight deals from Madison to Portland. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Portland. Data last updated June 9, 2026 and is based on user searches.
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.
Sun 6/216:00 am
MSN
- PDX
1 stop8h 40m
Delta
Sun 6/2812:33 am
PDX
- MSN
1 stop5h 39m
Delta
Deal found 6/4![Delta logo]()
$384
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.
Tue 6/232:42 pm
MSN
- PDX
1 stop8h 39m
American Airlines
Tue 6/3010:59 pm
PDX
- MSN
1 stop6h 46m
American Airlines
Deal found 6/4![American Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/296:00 am
MSN
- PDX
1 stop8h 40m
Delta
Fri 7/312:33 am
PDX
- MSN
1 stop7h 39m
Delta
Deal found 6/8![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 7/12:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Tue 7/712:33 am
PDX
- MSN
1 stop5h 38m
Delta
Deal found 6/8![Delta logo]()
$321
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:00 am
MSN
- PDX
1 stop6h 55m
American Airlines
Wed 7/811:41 pm
PDX
- MSN
1 stop8h 57m
American Airlines
Deal found 6/5![American Airlines logo]()
$367
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 7/22:45 pm
MSN
- PDX
1 stop7h 32m
Delta
Wed 7/83:00 pm
PDX
- MSN
1 stop6h 00m
Delta
Deal found 6/4![Delta logo]()
$364
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 7/115:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Tue 7/2111:40 pm
PDX
- MSN
1 stop8h 07m
United Airlines
Deal found 6/5![United Airlines logo]()
$331
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.
Sat 7/1112:03 pm
MSN
- PDX
1 stop7h 32m
Delta
Sat 7/1812:33 am
PDX
- MSN
1 stop5h 38m
Delta
Deal found 6/5![Delta logo]()
$345
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.
Wed 7/156:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Tue 7/2111:41 pm
PDX
- MSN
1 stop8h 57m
American Airlines
Deal found 6/4![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 7/156:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Sun 7/1911:15 pm
PDX
- MSN
1 stop7h 56m
American Airlines
Deal found 6/7![American Airlines logo]()
$375
One-way flights from Madison to PortlandSearch for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:59 pm
MSN
- PDX
1 stop22h 58m
Frontier
Deal found 6/5![Frontier logo]()
$166
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:55 pm
MSN
- PDX
1 stop22h 56m
Frontier
Deal found 6/8![Frontier logo]()
$206
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.
Tue 7/146:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/4![American Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:55 pm
MSN
- PDX
1 stop22h 41m
Frontier
Deal found 6/8![Frontier logo]()
$230
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.
Fri 7/249:10 am
MSN
- PDX
1 stop28h 25m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$247
This Mytrip deal was found by Cheapflights users on 6/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/147:59 pm
MSN
- PDX
1 stop22h 58m
Frontier
Deal found 6/8![Frontier logo]()
$255
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.
Wed 7/156:05 pm
MSN
- PDX
2 stops23h 02m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$269
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.
Fri 10/306:15 am
MSN
- PDX
1 stop6h 21m
Delta
Deal found 6/4![Delta logo]()
$288
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/5![American Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Tue 7/1410:48 am
MSN
- PDX
2 stops12h 06m
United Airlines
Deal found 6/8![United Airlines logo]()
$323
Find flight deals from Madison to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Portland (PDX). 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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $166 (CheapOair) |
Popular in | March |
Cheapest in | February |
Average price | $378 |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to Portland 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 9, 2026.
Use the filters below to find and compare flights from Madison to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Thu 7/2
6:00 am-10:40 am
1 stop6h 40m
Portland
Sun 7/5
12:33 am-8:12 am
1 stop5h 39m
$359
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Thu 7/2
2:45 pm-8:17 pm
1 stop7h 32m
Portland
Wed 7/8
3:00 pm-11:00 pm
1 stop6h 00m
$364
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Tue 9/22
2:44 pm-7:18 pm
1 stop6h 34m
Portland
Tue 9/29
10:43 am-10:35 pm
2 stops9h 52m
$426
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Sat 6/27
2:45 pm-8:17 pm
1 stop7h 32m
Portland
Sun 6/28
12:33 am-8:12 am
1 stop5h 39m
$429
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Tue 10/20
7:55 pm-11:47 pm
1 stop5h 52m
Portland
Sun 10/25
7:40 pm-10:15 am
2 stops12h 35m
$463
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Sun 6/21
5:00 am-9:48 am
1 stop6h 48m
Portland
Tue 6/30
10:40 pm-9:59 am
1 stop9h 19m
$470
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Fri 10/16
2:49 pm-10:57 pm
2 stops10h 08m
Portland
Sat 10/24
12:45 pm-9:07 pm
1 stop6h 22m
$480
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Fri 8/21
6:05 am-10:46 am
1 stop6h 41m
Portland
Mon 8/31
8:44 pm-8:16 am
2 stops9h 32m
$492
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Tue 9/8
6:15 am-3:06 pm
2 stops10h 51m
Portland
Fri 9/18
8:44 pm-8:22 am
2 stops9h 38m
$530
MadisonPortland
MSN - PDX
MSNPDX
Madison Truax Field
Mon 8/3
5:00 am-9:34 am
1 stop6h 34m
Portland
Tue 8/11
7:00 am-8:53 pm
2 stops11h 53m
$534
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Madison to Portland
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 Madison to Portland in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Madison-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Portland 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 Madison-Portland 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 Madison to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Madison with our price prediction graph.
MSN-PDX
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 Madison to Portland
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How far ahead should I book a flight from Madison to Portland?
To ensure you get the cheapest price possible for a flight from Madison to Portland, you should look to book at least 25 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Madison to Portland?
Currently, February is the cheapest month in which you can book a flight from Madison to Portland (average of $347). Flying from Madison to Portland in March is currently the most expensive (average of $543). 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 Madison to Portland?
What’s the top layover airport for flights from Madison to Portland?
Share of 1-stop round-trip flights from Madison to Portland chosen by Cheapflights users in the past 12 months, using the same layover each way.
Denver (DEN) – chosen by Cheapflights users on 60% of 1-stop itineraries from Madison to Portland on Cheapflights.
What’s the cheapest layover airport for flights from Madison to Portland?
Average round-trip fare for 1-stop flights from Madison to Portland, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $300.
What’s the fastest layover option from Madison to Portland?
Shortest average travel time for 1-stop one-way flights from Madison to Portland, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Chicago (ORD) have the shortest average one-way travel time for 1-stop routes: 7h 06m.
Which airport typically offers the quickest layover for flights from Madison to Portland?
Average layover duration for 1-stop one-way flights from Madison to Portland, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Chicago (ORD) offer the fastest connection on this route, with an average layover time of 1h 49m.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated June 9, 2026.
Read through reviews of airlines operating flights from Madison to Portland, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Madison to Portland. 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 Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham
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Madison and Portland flights
Browse other Madison and Portland flight options. Last updated on June 9, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
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Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
Top 4 airlines flying from Madison to Portland
Discover the top 4 airlines that operate flights from Madison to Portland. 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$238 | Average$303 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$288 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$288 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$288 | Average$438 | FlexibilityNo cancel fee | On-timeN/A |