$179+ Cheap flights from Madison to Portland (MSN - PDX)
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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PDX
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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 Madison to Portland
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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 September 11, 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 September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/288:00 am -
1 stop10h 26m
Tue 11/31:22 pm -
1 stop8h 51m
Deal found 9/10![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:49 pm -
1 stop8h 38m
Tue 11/101:15 pm -
1 stop5h 28m
Deal found 9/9![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:00 pm -
1 stop7h 02m
Sat 10/2411:51 am -
1 stop5h 15m
Deal found 9/9![Delta 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.
Sat 10/246:00 am -
1 stop6h 34m
Tue 11/31:44 pm -
1 stop5h 39m
Deal found 9/7![Delta logo]()
$351
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 10/286:25 am -
2 stops8h 57m
Sat 11/71:15 pm -
1 stop5h 28m
Deal found 9/8![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.
Wed 11/115:43 pm -
1 stop6h 44m
Sat 11/141:15 pm -
2 stops7h 52m
Deal found 9/6![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 9/10. 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 11/137:49 pm -
1 stop5h 57m
Mon 11/1611:20 pm -
1 stop7h 58m
Deal found 9/10![Delta 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.
Fri 10/237:46 pm -
1 stop5h 58m
Tue 11/311:51 am -
1 stop5h 15m
Deal found 9/7![Delta logo]()
$365
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 10/35:10 am -
2 stops9h 00m
Sat 10/107:02 am -
1 stop6h 02m
Deal found 9/7![United Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/87:05 pm -
1 stop6h 54m
Wed 10/1410:55 pm -
1 stop7h 16m
Deal found 9/10![American Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/102:52 pm -
1 stop10h 31m
Tue 12/2911:31 pm -
1 stop6h 57m
Deal found 9/10![American Airlines logo]()
$379
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 September 11, 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 September 11, 2026.
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.
Thu 12/36:30 am -
1 stop6h 56m
Sat 12/55:00 am -
2 stops10h 00m
Deal found 9/6![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 9/10. 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 9/263:00 pm -
1 stop7h 16m
Thu 10/15:49 pm -
2 stops12h 33m
Deal found 9/10![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:10 pm -
2 stops10h 24m
Tue 10/2011:30 pm -
1 stop8h 24m
Deal found 9/9![United Airlines logo]()
$450
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.
Fri 10/26:00 am -
1 stop8h 37m
Tue 10/68:44 pm -
2 stops11h 35m
Deal found 9/8![Delta logo]()
$457
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.
Wed 10/75:00 am -
2 stops11h 27m
Sat 10/108:25 am -
2 stops12h 10m
Deal found 9/6![United Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 9/10. 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 12/31:26 pm -
2 stops10h 40m
Sat 12/511:53 am -
1 stop7h 37m
Deal found 9/10![Delta logo]()
$473
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.
Fri 10/162:49 pm -
2 stops11h 45m
Sat 10/2410:43 am -
1 stop8h 17m
Deal found 9/6![United Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am -
1 stop6h 49m
Sat 10/37:00 am -
2 stops13h 41m
Deal found 9/9![Delta logo]()
$489
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 10/35:10 am -
2 stops11h 17m
Sat 10/108:25 am -
2 stops12h 10m
Deal found 9/7![United Airlines logo]()
$475
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.
Sun 9/275:10 am -
2 stops8h 55m
Sat 10/310:43 am -
2 stops9h 52m
Deal found 9/6![United Airlines logo]()
$489
Last-minute flights from Madison to PortlandDiscover last-minute flight deals from Madison to Portland. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Portland. Data last updated September 11, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/254:10 pm -
1 stop8h 13m
Sat 10/32:27 pm -
1 stop6h 08m
Deal found 9/10![United Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 9/10. 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 9/266:00 am -
1 stop8h 37m
Fri 10/212:25 am -
1 stop5h 57m
Deal found 9/10![Delta 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.
Fri 10/25:51 pm -
1 stop7h 32m
Tue 10/611:49 pm -
1 stop9h 06m
Deal found 9/8![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:51 pm -
1 stop7h 32m
Fri 10/910:55 pm -
1 stop7h 16m
Deal found 9/9![American Airlines logo]()
$389
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 10/35:10 am -
2 stops9h 00m
Sat 10/107:02 am -
1 stop6h 02m
Deal found 9/7![United Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/87:05 pm -
1 stop6h 54m
Wed 10/1410:55 pm -
1 stop7h 16m
Deal found 9/10![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:00 pm -
1 stop7h 02m
Sat 10/2411:51 am -
1 stop5h 15m
Deal found 9/9![Delta 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.
Fri 10/237:46 pm -
1 stop5h 58m
Tue 11/311:51 am -
1 stop5h 15m
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.
Sat 10/246:00 am -
1 stop6h 34m
Tue 11/31:44 pm -
1 stop5h 39m
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.
Sun 10/256:00 am -
1 stop6h 34m
Wed 11/411:51 am -
1 stop5h 15m
Deal found 9/7![Delta logo]()
$385
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/288:00 am -
1 stop10h 26m
Tue 11/31:22 pm -
1 stop8h 51m
Deal found 9/10![American Airlines logo]()
$331
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 10/286:25 am -
2 stops8h 57m
Sat 11/71:15 pm -
1 stop5h 28m
Deal found 9/8![United Airlines logo]()
$352
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 September 11, 2026.
Search for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:45 pm -
2 stops45h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$179
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:00 pm -
1 stop17h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/3110:38 am -
2 stops27h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$209
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 10/2710:30 am -
2 stops51h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$212
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.
Sat 10/2410:38 am -
3 stops26h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/135:00 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$283
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.
Thu 9/176:00 pm -
2 stops19h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$284
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.
Wed 10/216:00 am -
1 stop6h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$293
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (American Airlines) |
One-way from | $179 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $379 |
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 7,457,451 searches. Data last updated September 11, 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
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Sat 10/31
10:38 am-12:12 pm
3 stops27h 34m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$272
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Wed 10/21
6:00 am-10:34 am
1 stop6h 34m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$293
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Sat 10/24
10:38 am-10:54 am
3 stops26h 16m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$297
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Thu 11/26
6:10 am-2:16 pm
1 stop10h 06m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$303
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Fri 10/30
8:00 am-4:26 pm
1 stop10h 26m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$303
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Sat 10/24
8:50 am-3:05 pm
1 stop8h 15m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$303
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Fri 10/30
6:00 am-10:34 am
1 stop6h 34m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$303
Quickest round-trip
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Fri 10/23
7:46 pm-11:44 pm
1 stop5h 58m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$313
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Mon 10/26
7:46 pm-11:44 pm
1 stop5h 58m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$313
MadisonPortland
MSN Madison Truax Field - PDX Portland
MSNPDX
Madison Truax Field
Mon 9/28
5:00 am-10:55 am
1 stop7h 55m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$334
Showing 1-10 of 20 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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
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 50 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 $360). 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?
Airfare is below average for this route at the moment.
Madison to Portland flights typically cost between $332 and $513 in October.The cheapest round-trip price found within the last 5 days was $331 on American Airlines (Oct 28-Nov 3).
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 September 11, 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.
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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
Lincoln City
Durham
Longview
Lake Oswego
Vancouver
Kelso
Troutdale
Clackamas
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
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Madison and Portland flights
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Top 3 airlines flying from Madison to Portland
Discover the top 3 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$444 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$309 | Average$463 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$320 | Average$446 | FlexibilityNo cancel fee | On-timeN/A |