$209+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MSN
Mei 29 — Jun 51
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 April 29, 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 April 29, 2026.
This Delta deal was found by Cheapflights users on 4/25. 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.
Sel 5/2611:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Rab 6/32:33 pm
MSN
- PDX
1 stop7h 38m
Delta
Deal found 4/25![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Jum 7/310:40 pm
PDX
- MSN
1 stop8h 15m
United Airlines
Sab 7/115:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 4/28![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 4/27. 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.
Sel 5/2611:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Min 5/315:43 am
MSN
- PDX
1 stop9h 11m
Delta
Deal found 4/27![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Jum 8/212:15 pm
PDX
- MSN
1 stop6h 27m
United Airlines
Sen 8/245:00 am
MSN
- PDX
1 stop6h 29m
United Airlines
Deal found 4/28![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sab 6/2010:40 pm
PDX
- MSN
1 stop8h 15m
United Airlines
Rab 6/245:00 am
MSN
- PDX
1 stop6h 39m
United Airlines
Deal found 4/28![United Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Jum 7/312:59 am
PDX
- MSN
1 stop7h 39m
American Airlines
Kam 7/96:45 pm
MSN
- PDX
1 stop7h 12m
American Airlines
Deal found 4/25![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 4/28. 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.
Kam 6/411:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Min 6/76:00 am
MSN
- PDX
1 stop6h 39m
Delta
Deal found 4/28![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/25. 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.
Min 5/2411:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Sen 6/16:30 am
MSN
- PDX
1 stop6h 23m
Delta
Deal found 4/25![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sab 7/1810:57 pm
PDX
- MSN
1 stop6h 54m
American Airlines
Rab 7/225:11 pm
MSN
- PDX
1 stop9h 44m
American Airlines
Deal found 4/28![American Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 4/25. 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.
Min 5/2411:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Sab 6/66:30 am
MSN
- PDX
2 stops11h 26m
Delta
Deal found 4/25![Delta logo]()
$404
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sab 5/26:00 am
PDX
- MSN
1 stop9h 22m
American Airlines
Sel 5/57:45 am
MSN
- PDX
1 stop6h 48m
American Airlines
Deal found 4/28![American Airlines logo]()
$413
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 April 29, 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 April 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Kam 5/2810:40 pm
PDX
- MSN
1 stop7h 26m
United Airlines
Rab 6/36:30 am
MSN
- PDX
1 stop7h 08m
United Airlines
Deal found 4/27![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 4/27. 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.
Sel 9/812:40 am
PDX
- MSN
1 stop5h 40m
Delta
Min 9/139:00 am
MSN
- PDX
1 stop5h 54m
Delta
Deal found 4/27![Delta logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 5/267:00 am
PDX
- MSN
1 stop9h 14m
Alaska Airlines
Sab 5/302:03 pm
MSN
- PDX
2 stops11h 56m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$474
This Delta deal was found by Cheapflights users on 4/28. 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.
Kam 6/411:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Min 6/76:00 am
MSN
- PDX
1 stop6h 39m
Delta
Deal found 4/28![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Kam 5/2810:40 pm
PDX
- MSN
1 stop9h 19m
United Airlines
Sab 6/65:45 pm
MSN
- PDX
1 stop8h 08m
United Airlines
Deal found 4/25![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 4/24. 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.
Min 6/1412:31 am
PDX
- MSN
1 stop5h 51m
Delta
Min 6/216:00 am
MSN
- PDX
1 stop6h 44m
Delta
Deal found 4/24![Delta logo]()
$404
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sab 5/239:44 am
PDX
- MSN
2 stops11h 22m
Alaska Airlines
Rab 6/36:30 am
MSN
- PDX
2 stops12h 20m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Min 7/1910:40 pm
PDX
- MSN
1 stop9h 19m
United Airlines
Sab 7/255:00 am
MSN
- PDX
1 stop6h 34m
United Airlines
Deal found 4/24![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 4/27. 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.
Kam 5/288:11 pm
PDX
- MSN
2 stops10h 15m
Delta
Rab 6/32:33 pm
MSN
- PDX
1 stop7h 38m
Delta
Deal found 4/27![Delta logo]()
$448
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sab 5/98:45 am
PDX
- MSN
2 stops11h 26m
Alaska Airlines
Rab 5/137:50 am
MSN
- PDX
2 stops11h 00m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Rab 9/97:13 pm
PDX
- MSN
2 stops12h 31m
United Airlines
Min 9/136:30 am
MSN
- PDX
1 stop7h 05m
United Airlines
Deal found 4/29![United Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 4/24. 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.
Jum 5/1511:12 pm
PDX
- MSN
1 stop9h 04m
Delta
Rab 5/201:29 pm
MSN
- PDX
2 stops12h 26m
Delta
Deal found 4/24![Delta logo]()
$477
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated April 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Sab 5/26:00 am
PDX
- MSN
1 stop9h 22m
American Airlines
Sel 5/57:45 am
MSN
- PDX
1 stop6h 48m
American Airlines
Deal found 4/28![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Jum 5/152:38 pm
PDX
- MSN
1 stop6h 16m
United Airlines
Rab 5/203:56 pm
MSN
- PDX
1 stop8h 39m
United Airlines
Deal found 4/24![United Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 4/28. 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.
Jum 5/2211:12 pm
PDX
- MSN
1 stop9h 04m
Delta
Sen 5/255:43 am
MSN
- PDX
1 stop9h 11m
Delta
Deal found 4/28![Delta logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Jum 5/2210:41 am
PDX
- MSN
2 stops30h 34m
Multiple Airlines
Jum 6/59:10 am
MSN
- PDX
1 stop28h 40m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 4/25. 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.
Jum 5/2211:12 pm
PDX
- MSN
1 stop9h 04m
Delta
Sab 6/66:30 am
MSN
- PDX
2 stops11h 26m
Delta
Deal found 4/25![Delta logo]()
$428
This Delta deal was found by Cheapflights users on 4/25. 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.
Min 5/2411:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Sen 6/16:30 am
MSN
- PDX
1 stop6h 23m
Delta
Deal found 4/25![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 4/25. 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.
Min 5/246:15 am
PDX
- MSN
1 stop5h 38m
Delta
Rab 6/36:30 am
MSN
- PDX
2 stops13h 31m
Delta
Deal found 4/25![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Min 5/242:27 pm
PDX
- MSN
1 stop6h 38m
United Airlines
Sab 6/65:45 pm
MSN
- PDX
1 stop6h 46m
United Airlines
Deal found 4/25![United Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 4/25. 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.
Sel 5/2611:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Rab 6/32:33 pm
MSN
- PDX
1 stop7h 38m
Delta
Deal found 4/25![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 4/27. 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.
Sel 5/2611:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Min 5/315:43 am
MSN
- PDX
1 stop9h 11m
Delta
Deal found 4/27![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 4/25. 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.
Sel 5/261:35 pm
PDX
- MSN
2 stops16h 51m
Delta
Kam 6/411:48 am
MSN
- PDX
1 stop7h 27m
Delta
Deal found 4/25![Delta logo]()
$431
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Kam 5/285:05 am
PDX
- MSN
1 stop6h 54m
American Airlines
Kam 5/286:44 pm
MSN
- PDX
1 stop7h 08m
American Airlines
Deal found 4/25![American Airlines logo]()
$433
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 April 29, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Rab 5/2711:40 pm
PDX
- MSN
1 stop8h 19m
United Airlines
Deal found 4/28![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sel 9/2212:50 pm
PDX
- MSN
2 stops9h 14m
United Airlines
Deal found 4/28![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 4/24. 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.
Sen 5/2511:12 pm
PDX
- MSN
1 stop7h 37m
Delta
Deal found 4/24![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Rab 8/2610:35 am
PDX
- MSN
2 stops8h 30m
United Airlines
Deal found 4/27![United Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sen 5/1812:35 pm
PDX
- MSN
2 stops42h 39m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 4/24. 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.
Min 5/246:00 am
PDX
- MSN
1 stop5h 53m
Delta
Deal found 4/24![Delta logo]()
$259
This Expedia deal was found by Cheapflights users on 4/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 5/199:44 am
PDX
- MSN
2 stops11h 57m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Kam 8/275:42 pm
PDX
- MSN
1 stop22h 28m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/28. 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.
Jum 6/2612:33 am
PDX
- MSN
1 stop7h 39m
Delta
Deal found 4/28![Delta logo]()
$280
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sab 8/2210:35 am
PDX
- MSN
2 stops10h 07m
United Airlines
Deal found 4/28![United Airlines logo]()
$285
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (Delta) |
One-way from | $209 (United Airlines) |
Popular in | March |
Cheapest in | February |
Average price | $453 |
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 April 29, 2026.
Use the filters below to find and compare flights from Portland to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMadison
PDX - MSN
PDXMSN
Portland
Kam 5/28
10:40 pm-8:06 am
1 stop7h 26m
Madison Truax Field
Rab 6/3
6:30 am-11:38 am
1 stop7h 08m
$321
Quickest round-trip
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sel 9/8
12:40 am-8:20 am
1 stop5h 40m
Madison Truax Field
Min 9/13
9:00 am-12:54 pm
1 stop5h 54m
$345
PortlandMadison
PDX - MSN
PDXMSN
Portland
Kam 6/4
11:12 pm-8:49 am
1 stop7h 37m
Madison Truax Field
Min 6/7
6:00 am-10:39 am
1 stop6h 39m
$369
PortlandMadison
PDX - MSN
PDXMSN
Portland
Min 6/14
12:31 am-8:22 am
1 stop5h 51m
Madison Truax Field
Min 6/21
6:00 am-10:44 am
1 stop6h 44m
$404
PortlandMadison
PDX - MSN
PDXMSN
Portland
Kam 5/28
10:40 pm-9:59 am
1 stop9h 19m
Madison Truax Field
Sab 6/6
5:45 pm-11:53 pm
1 stop8h 08m
$421
PortlandMadison
PDX - MSN
PDXMSN
Portland
Kam 5/28
8:11 pm-8:26 am
2 stops10h 15m
Madison Truax Field
Rab 6/3
2:33 pm-8:11 pm
1 stop7h 38m
$448
PortlandMadison
PDX - MSN
PDXMSN
Portland
Min 7/19
10:40 pm-9:59 am
1 stop9h 19m
Madison Truax Field
Sab 7/25
5:00 am-9:34 am
1 stop6h 34m
$469
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sel 5/26
7:00 am-6:14 pm
1 stop9h 14m
Madison Truax Field
Sab 5/30
2:03 pm-11:59 pm
2 stops11h 56m
$474
PortlandMadison
PDX - MSN
PDXMSN
Portland
Jum 5/15
11:12 pm-10:16 am
1 stop9h 04m
Madison Truax Field
Rab 5/20
1:29 pm-11:55 pm
2 stops12h 26m
$477
PortlandMadison
PDX - MSN
PDXMSN
Portland
Sab 5/23
9:44 am-11:06 pm
2 stops11h 22m
Madison Truax Field
Rab 6/3
6:30 am-4:50 pm
2 stops12h 20m
$479
Showing 1-10 of 22 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Madison flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Portland with our price prediction graph.
PDX-MSN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Madison
How far ahead should I book a flight from Portland to Madison?
The price you pay for your flight from Portland to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 8 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Portland to Madison?
Currently, February is the cheapest month in which you can book a flight from Portland to Madison (average of $398). Flying from Portland to Madison in March is currently the most expensive (average of $581). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Portland to Madison?
Reviews of airlines servicing Madison
Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated April 29, 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
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Food
7.1
Comfort
7.8
Entertainment
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Portland to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Madison?
Book flights to Madison if you plan to visit one of these locationsPortage
Sun Prairie
Middleton
Baraboo
Fitchburg
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Search flights from Portland to Madison by cabin class
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Other flights to Madison
Explore flights to Madison departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 29, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on April 29, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on April 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Portland to Madison
Discover the top 5 airlines that operate flights from Portland to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$258 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$288 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$288 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$463 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$379 | Average$630 | FlexibilityNo cancel fee | On-time75% |