$203+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Jul 11 — Jul 181
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 11, 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 11, 2026.
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 8/2512:35 am
PDX
- MSN
1 stop5h 41m
Delta
Tue 9/86:15 am
MSN
- PDX
1 stop8h 39m
Delta
Deal found 6/10![Delta 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 United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:40 pm
PDX
- MSN
1 stop9h 07m
United Airlines
Tue 7/145:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/9![United 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 7/2211:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Wed 7/292:55 pm
MSN
- PDX
1 stop8h 55m
American Airlines
Deal found 6/7![American Airlines logo]()
$336
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:33 am
PDX
- MSN
1 stop7h 39m
Delta
Sat 7/112:45 pm
MSN
- PDX
1 stop7h 30m
Delta
Deal found 6/9![Delta logo]()
$340
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.
Wed 9/911:39 am
PDX
- MSN
1 stop8h 18m
Delta
Sun 9/135:55 pm
MSN
- PDX
1 stop7h 39m
Delta
Deal found 6/6![Delta logo]()
$345
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:40 pm
PDX
- MSN
1 stop7h 59m
United Airlines
Sun 7/195:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/9![United Airlines logo]()
$349
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 9/212:35 am
PDX
- MSN
1 stop5h 41m
Delta
Mon 9/712:10 pm
MSN
- PDX
1 stop7h 24m
Delta
Deal found 6/8![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 7/31:34 pm
PDX
- MSN
1 stop7h 19m
American Airlines
Sat 7/115:11 pm
MSN
- PDX
1 stop9h 44m
American Airlines
Deal found 6/10![American Airlines logo]()
$367
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 11, 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 11, 2026.
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 9/2012:20 am
PDX
- MSN
1 stop6h 02m
Delta
Sat 9/266:10 am
MSN
- PDX
1 stop6h 29m
Delta
Deal found 6/10![Delta logo]()
$335
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:17 am
PDX
- MSN
1 stop8h 39m
United Airlines
Tue 9/16:30 am
MSN
- PDX
1 stop6h 58m
United Airlines
Deal found 6/9![United Airlines logo]()
$421
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 9/812:40 am
PDX
- MSN
1 stop5h 40m
Delta
Sun 9/135:55 pm
MSN
- PDX
1 stop7h 39m
Delta
Deal found 6/8![Delta logo]()
$340
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 8/512:35 am
PDX
- MSN
1 stop5h 41m
Delta
Tue 8/1112:10 pm
MSN
- PDX
1 stop7h 24m
Delta
Deal found 6/8![Delta logo]()
$340
This United Airlines 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 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 6/9![United Airlines logo]()
$426
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.
Wed 9/912:40 am
PDX
- MSN
1 stop5h 40m
Delta
Sun 9/135:55 pm
MSN
- PDX
1 stop7h 39m
Delta
Deal found 6/6![Delta logo]()
$359
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.
Sat 9/58:40 am
PDX
- MSN
2 stops10h 13m
United Airlines
Wed 9/96:30 am
MSN
- PDX
1 stop6h 58m
United Airlines
Deal found 6/7![United Airlines logo]()
$426
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 7/212:33 am
PDX
- MSN
1 stop5h 39m
Delta
Sat 7/1112:03 pm
MSN
- PDX
1 stop7h 32m
Delta
Deal found 6/8![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 7/2710:40 pm
PDX
- MSN
1 stop9h 07m
United Airlines
Tue 8/45:00 am
MSN
- PDX
2 stops13h 47m
United Airlines
Deal found 6/10![United Airlines logo]()
$534
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.
Wed 10/1411:10 am
PDX
- MSN
2 stops9h 45m
Delta
Tue 10/2011:11 am
MSN
- PDX
2 stops12h 53m
Delta
Deal found 6/6![Delta logo]()
$505
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 7/311:16 am
PDX
- MSN
2 stops9h 56m
United Airlines
Sat 7/115:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/7![United Airlines logo]()
$589
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated June 11, 2026 and is based on user searches.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2510:59 pm
PDX
- MSN
1 stop6h 46m
American Airlines
Tue 6/306:42 pm
MSN
- PDX
1 stop7h 05m
American Airlines
Deal found 6/9![American Airlines logo]()
$394
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 6/9. 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 7/312:33 am
PDX
- MSN
1 stop7h 39m
Delta
Sat 7/112:45 pm
MSN
- PDX
1 stop7h 30m
Delta
Deal found 6/9![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 7/31:34 pm
PDX
- MSN
1 stop7h 19m
American Airlines
Sat 7/115:11 pm
MSN
- PDX
1 stop9h 44m
American Airlines
Deal found 6/10![American Airlines logo]()
$367
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:40 pm
PDX
- MSN
1 stop9h 07m
United Airlines
Tue 7/145:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/9![United Airlines logo]()
$335
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:40 pm
PDX
- MSN
1 stop7h 59m
United Airlines
Sun 7/195:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 6/9![United Airlines logo]()
$349
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 7/2211:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Wed 7/292:55 pm
MSN
- PDX
1 stop8h 55m
American Airlines
Deal found 6/7![American Airlines logo]()
$336
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2311:15 pm
PDX
- MSN
1 stop6h 36m
American Airlines
Sun 7/266:43 pm
MSN
- PDX
1 stop8h 07m
American Airlines
Deal found 6/9![American Airlines logo]()
$389
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 11, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated June 11, 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.
Tue 8/1112:35 am
PDX
- MSN
1 stop5h 41m
Delta
Deal found 6/8![Delta logo]()
$203
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:20 pm
PDX
- MSN
1 stop28h 50m
Frontier
Deal found 6/7![Frontier logo]()
$207
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:59 pm
PDX
- MSN
1 stop6h 46m
American Airlines
Deal found 6/9![American Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 8/912:35 am
PDX
- MSN
1 stop5h 41m
Delta
Deal found 6/10![Delta logo]()
$235
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 9/812:40 am
PDX
- MSN
1 stop5h 40m
Delta
Deal found 6/8![Delta logo]()
$268
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 8/95:15 am
PDX
- MSN
1 stop6h 34m
American Airlines
Deal found 6/10![American Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Thu 7/23:57 pm
PDX
- MSN
3 stops39h 50m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$290
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/309:30 am
PDX
- MSN
2 stops10h 00m
Delta
Deal found 6/9![Delta logo]()
$318
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:31 pm
PDX
- MSN
1 stop6h 42m
American Airlines
Deal found 6/9![American Airlines logo]()
$319
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.
Wed 9/98:40 am
PDX
- MSN
2 stops10h 13m
United Airlines
Deal found 6/8![United Airlines logo]()
$323
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:05 am
PDX
- MSN
2 stops10h 07m
United Airlines
Deal found 6/9![United Airlines logo]()
$324
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 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $203 (Delta) |
Popular in | May |
Cheapest in | February |
Average price | $491 |
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 11, 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
Quickest round-trip
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sun 9/20
12:20 am-8:22 am
1 stop6h 02m
Madison Truax Field
Sat 9/26
6:10 am-10:39 am
1 stop6h 29m
$335
PortlandMadison
PDX - MSN
PDXMSN
Portland
Tue 9/8
12:40 am-8:20 am
1 stop5h 40m
Madison Truax Field
Sun 9/13
5:55 pm-11:34 pm
1 stop7h 39m
$340
PortlandMadison
PDX - MSN
PDXMSN
Portland
Wed 8/5
12:35 am-8:16 am
1 stop5h 41m
Madison Truax Field
Tue 8/11
12:10 pm-5:34 pm
1 stop7h 24m
$340
PortlandMadison
PDX - MSN
PDXMSN
Portland
Wed 9/9
12:40 am-8:20 am
1 stop5h 40m
Madison Truax Field
Sun 9/13
5:55 pm-11:34 pm
1 stop7h 39m
$359
PortlandMadison
PDX - MSN
PDXMSN
Portland
Thu 7/2
12:33 am-8:12 am
1 stop5h 39m
Madison Truax Field
Sat 7/11
12:03 pm-5:35 pm
1 stop7h 32m
$370
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sat 8/29
8:17 am-6:56 pm
1 stop8h 39m
Madison Truax Field
Tue 9/1
6:30 am-11:28 am
1 stop6h 58m
$421
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
Sat 9/5
8:40 am-8:53 pm
2 stops10h 13m
Madison Truax Field
Wed 9/9
6:30 am-11:28 am
1 stop6h 58m
$426
PortlandMadison
PDX - MSN
PDXMSN
Portland
Wed 10/14
11:10 am-10:55 pm
2 stops9h 45m
Madison Truax Field
Tue 10/20
11:11 am-10:04 pm
2 stops12h 53m
$505
PortlandMadison
PDX - MSN
PDXMSN
Portland
Mon 7/27
10:40 pm-9:47 am
1 stop9h 07m
Madison Truax Field
Tue 8/4
5:00 am-4:47 pm
2 stops13h 47m
$534
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 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 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 $398). Flying from Portland to Madison in May is currently the most expensive (average of $585). 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 11, 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.
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Entertainment
7.0
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Related info for your journey
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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 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$288 | Average$509 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$288 | Average$491 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$464 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$317 | Average$585 | FlexibilityNo cancel fee | On-time75% |