$163+ Cheap flights from Portland, ME (PWM) to Wisconsin
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Wisconsin with Cheapflights
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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
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Cheapest flights from Portland to WisconsinExplore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
This American Airlines deal was found by Cheapflights users on 10/2. 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 12/412:44 pm -
1 stop6h 11m
Mon 12/75:36 am -
1 stop5h 22m
Deal found 10/2![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:45 pm -
1 stop6h 27m
Sat 10/316:46 am -
1 stop4h 45m
Deal found 9/28![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:50 pm -
1 stop4h 25m
Mon 11/165:55 pm -
1 stop4h 26m
Deal found 9/29![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:08 pm -
1 stop4h 57m
Sat 10/3112:32 pm -
2 stops9h 49m
Deal found 9/28![United Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/213:41 pm -
1 stop5h 34m
Tue 10/275:00 am -
2 stops7h 26m
Deal found 9/30![United Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 10/286:28 am -
2 stops7h 07m
Sat 10/311:37 pm -
2 stops9h 33m
Deal found 9/28![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:45 pm -
1 stop7h 27m
Sun 11/15:50 am -
1 stop5h 03m
Deal found 9/29![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/30. 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 10/291:52 pm -
2 stops9h 35m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 9/30![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:42 pm -
1 stop4h 23m
Fri 10/302:59 pm -
1 stop7h 36m
Deal found 9/29![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/25:08 pm -
1 stop6h 07m
Wed 11/43:33 pm -
2 stops6h 48m
Deal found 9/29![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/205:15 am -
2 stops8h 15m
Sat 10/246:20 am -
2 stops7h 18m
Deal found 9/29![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/226:00 am -
1 stop6h 54m
Mon 10/265:31 pm -
1 stop5h 05m
Deal found 9/30![American Airlines logo]()
$349
Best flights from Portland to WisconsinDiscover carefully curated flight deals from Portland to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
Discover carefully curated flight deals from Portland to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
This American Airlines deal was found by Cheapflights users on 10/2. 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 12/412:44 pm -
1 stop6h 11m
Mon 12/75:36 am -
1 stop5h 22m
Deal found 10/2![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:01 am -
1 stop8h 53m
Wed 10/289:35 am -
1 stop5h 27m
Deal found 9/29![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:40 am -
1 stop7h 15m
Thu 10/295:00 pm -
1 stop3h 55m
Deal found 9/29![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:08 pm -
1 stop4h 57m
Sat 10/3112:32 pm -
2 stops9h 49m
Deal found 9/28![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:45 pm -
1 stop6h 27m
Sat 10/316:46 am -
1 stop4h 45m
Deal found 9/28![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:09 pm -
1 stop7h 48m
Wed 11/49:35 am -
1 stop5h 27m
Deal found 9/29![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/206:00 am -
1 stop7h 30m
Sat 10/241:17 pm -
1 stop7h 29m
Deal found 9/29![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 10/286:28 am -
2 stops7h 07m
Sat 10/311:37 pm -
2 stops9h 33m
Deal found 9/28![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 9/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:20 am -
2 stops6h 25m
Fri 11/66:25 pm -
1 stop4h 30m
Deal found 9/30![Southwest logo]()
$370
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/25:08 pm -
1 stop6h 07m
Wed 11/43:33 pm -
2 stops6h 48m
Deal found 9/29![United Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/226:00 am -
1 stop6h 54m
Mon 10/265:31 pm -
1 stop5h 05m
Deal found 9/30![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/3. 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 10/291:52 pm -
2 stops9h 35m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 10/3![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/216:00 am -
1 stop7h 30m
Wed 10/288:00 am -
1 stop5h 16m
Deal found 10/1![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:03 pm -
2 stops11h 54m
Wed 10/2811:33 am -
1 stop4h 31m
Deal found 9/29![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/274:15 pm -
1 stop5h 20m
Fri 10/305:30 am -
1 stop6h 32m
Deal found 9/29![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:25 pm -
1 stop6h 55m
Fri 12/189:55 am -
1 stop5h 45m
Deal found 10/2![Southwest logo]()
$434
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/308:49 am -
2 stops7h 09m
Fri 11/63:33 pm -
2 stops6h 48m
Deal found 9/30![United Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 10/3. 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 10/302:09 pm -
1 stop9h 00m
Sun 11/15:35 am -
1 stop6h 27m
Deal found 10/3![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:37 pm -
1 stop5h 54m
Sun 10/186:10 am -
1 stop5h 01m
Deal found 9/29![American Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:09 pm -
1 stop8h 59m
Wed 10/285:35 am -
1 stop6h 27m
Deal found 9/29![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/155:08 pm -
1 stop6h 27m
Mon 10/198:17 am -
1 stop5h 21m
Deal found 10/1![United Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/30. 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 11/173:41 pm -
1 stop8h 09m
Wed 11/186:47 am -
1 stop6h 29m
Deal found 9/30![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 10/2. 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 1/69:10 am -
2 stops9h 01m
Sat 1/98:00 am -
2 stops12h 03m
Deal found 10/2![United Airlines logo]()
$449
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated October 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/205:15 am -
2 stops8h 15m
Sat 10/246:20 am -
2 stops7h 18m
Deal found 9/29![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/213:41 pm -
1 stop5h 34m
Tue 10/275:00 am -
2 stops7h 26m
Deal found 9/30![United Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/226:00 am -
1 stop6h 54m
Mon 10/265:31 pm -
1 stop5h 05m
Deal found 9/30![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:45 pm -
1 stop6h 27m
Sat 10/316:46 am -
1 stop4h 45m
Deal found 9/28![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/285:08 pm -
1 stop4h 57m
Sat 10/3112:32 pm -
2 stops9h 49m
Deal found 9/28![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 10/286:28 am -
2 stops7h 07m
Sat 10/311:37 pm -
2 stops9h 33m
Deal found 9/28![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:01 am -
1 stop8h 53m
Wed 10/285:55 pm -
1 stop4h 23m
Deal found 9/29![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:45 pm -
1 stop7h 27m
Sun 11/15:50 am -
1 stop5h 03m
Deal found 9/29![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/30. 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 10/291:52 pm -
2 stops9h 35m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 9/30![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/3. 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 10/302:09 pm -
1 stop9h 00m
Sun 11/15:35 am -
1 stop6h 27m
Deal found 10/3![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Mon 11/25:08 pm -
1 stop6h 07m
Wed 11/43:33 pm -
2 stops6h 48m
Deal found 9/29![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:50 pm -
1 stop4h 25m
Mon 11/165:55 pm -
1 stop4h 26m
Deal found 9/29![Delta logo]()
$325
One-way flights from Portland to WisconsinSearch for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 10/226:55 pm -
1 stop5h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![United Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 9/28. 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.
Fri 10/236:01 am -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$183
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sun 11/16:00 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![American Airlines logo]()
$235
This American Airlines deal was found by Cheapflights users on 10/2. 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 10/225:37 pm -
1 stop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Sat 12/1212:28 pm -
2 stops21h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 10/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 am -
2 stops6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 10/1. 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 10/314:47 pm -
1 stop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/309:48 am -
1 stop26h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$275
This Sun Country Air deal was found by Cheapflights users on 9/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:35 pm -
1 stop5h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Sun Country Air logo]()
$283
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/275:08 pm -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 10/236:00 am -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:27 pm -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![American Airlines logo]()
$294
Find flight deals from Portland to Wisconsin
Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated October 3, 2026.
Round-trip from | $289 (American Airlines) |
|---|---|
One-way from | $163 (United Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $419 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Wisconsin 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 October 3, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Sat 11/14
4:03 pm-8:40 pm
1 stop5h 37m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Thu 10/22
5:30 am-12:14 pm
1 stop7h 44m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Thu 10/22
6:55 pm-11:37 pm
1 stop5h 42m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Fri 11/13
5:10 pm-11:10 pm
2 stops7h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$188
PortlandAppleton
PWM Portland - ATW Appleton Intl
PWMATW
Portland
Sat 12/12
12:28 pm-8:56 am
2 stops21h 28m
Appleton Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$262
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Thu 10/22
5:20 am-10:45 am
2 stops6h 25m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$264
PortlandAppleton
PWM Portland - ATW Appleton Intl
PWMATW
Portland
Sat 10/31
4:47 pm-9:15 pm
1 stop5h 28m
Appleton Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$266
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Thu 10/8
12:35 pm-5:02 pm
1 stop5h 27m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$283
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 10/29
5:45 pm-12:12 am
1 stop7h 27m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 10/27
5:08 pm-9:05 pm
1 stop4h 57m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
Showing 1-10 of 47 resultsSorted by cheapest first
Best time to book a flight from Portland to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Portland with our price prediction graph.
PWM-MKE
PWM-ATW
PWM-MSN
PWM-GRB
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 Wisconsin
PWM-USWI
PWM-MKE
PWM-ATW
PWM-MSN
PWM-GRB
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $348). Flying from Portland, Maine to Wisconsin in December is currently the most expensive (average of $583). 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, Maine to Wisconsin?
Airfare is below average for this route at the moment.
Portland, Maine to Wisconsin flights typically cost between $396 and $442 in November.The cheapest round-trip price found within the last 5 days was $325 on Delta (Nov 12-Nov 16).
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated October 3, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Portland to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Wisconsin
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Complete your trip
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Find flights from Portland to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Wisconsin flights
Browse other Portland and Wisconsin flight options. Last updated on October 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Wisconsin flights
Consider these flights traveling from Portland to Wisconsin.
Top 4 airlines flying from Portland to Wisconsin
Discover the top 4 airlines that operate flights from Portland to Wisconsin. 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 October 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$396 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$434 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$431 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$399 | FlexibilityNo cancel fee | On-time63% |