$139+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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 September 11, 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 September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:10 pm -
1 stop7h 18m
Tue 12/294:02 pm -
1 stop5h 58m
Deal found 9/7![American Airlines logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:10 pm -
1 stop7h 17m
Thu 11/125:00 am -
1 stop5h 58m
Deal found 9/10![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/295:08 pm -
1 stop6h 35m
Sun 11/18:00 am -
1 stop5h 16m
Deal found 9/11![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/11. 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 11/412:42 pm -
1 stop5h 36m
Sat 11/147:00 am -
1 stop3h 58m
Deal found 9/11![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:47 am -
1 stop4h 59m
Sat 11/146:15 am -
2 stops7h 12m
Deal found 9/9![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:37 pm -
1 stop6h 41m
Sat 10/172:58 pm -
1 stop7h 45m
Deal found 9/9![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:37 pm -
2 stops7h 35m
Tue 10/133:28 pm -
2 stops7h 08m
Deal found 9/8![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 9/11. 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 11/46:01 am -
1 stop7h 30m
Wed 11/115:20 am -
2 stops8h 56m
Deal found 9/11![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop6h 43m
Sat 10/33:25 pm -
1 stop7h 22m
Deal found 9/8![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/235:45 pm -
1 stop7h 12m
Sat 10/315:29 am -
1 stop6h 02m
Deal found 9/11![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop6h 43m
Sat 10/312:32 pm -
2 stops7h 49m
Deal found 9/11![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/11. 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 11/511:55 am -
1 stop8h 11m
Wed 11/114:01 pm -
1 stop6h 20m
Deal found 9/11![Delta logo]()
$335
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 September 11, 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 September 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:47 am -
1 stop4h 59m
Sat 11/143:15 pm -
1 stop5h 33m
Deal found 9/9![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:01 am -
1 stop8h 53m
Tue 10/272:59 pm -
1 stop7h 02m
Deal found 9/9![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:38 pm -
2 stops7h 19m
Wed 10/2811:33 am -
1 stop4h 31m
Deal found 9/10![American Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:10 pm -
2 stops7h 10m
Thu 12/315:30 am -
2 stops8h 15m
Deal found 9/7![Southwest logo]()
$459
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:08 pm -
1 stop6h 50m
Sat 10/318:00 am -
1 stop5h 16m
Deal found 9/11![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:55 am -
1 stop8h 11m
Wed 11/114:01 pm -
1 stop6h 20m
Deal found 9/11![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/44:10 pm -
2 stops9h 05m
Sat 11/75:47 am -
1 stop5h 06m
Deal found 9/11![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/275:30 am -
2 stops9h 26m
Tue 11/32:33 pm -
1 stop6h 18m
Deal found 9/11![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/11. 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 11/711:55 am -
1 stop8h 11m
Fri 11/134:01 pm -
1 stop6h 20m
Deal found 9/11![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
Nonstop2h 57m
Sat 10/36:59 am -
Nonstop2h 41m
Deal found 9/8![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:01 am -
2 stops12h 20m
Sun 11/15:30 am -
1 stop6h 32m
Deal found 9/7![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:08 pm -
Nonstop2h 57m
Sat 10/2411:04 am -
Nonstop2h 34m
Deal found 9/8![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/11. 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 10/233:25 pm -
2 stops10h 15m
Sun 10/255:45 am -
1 stop5h 45m
Deal found 9/11![Southwest logo]()
$462
This Delta deal was found by Cheapflights users on 9/11. 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 10/271:52 pm -
2 stops8h 50m
Tue 11/312:29 pm -
2 stops9h 49m
Deal found 9/11![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am -
2 stops11h 35m
Sun 9/275:05 pm -
1 stop5h 42m
Deal found 9/8![American Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 9/11. 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 10/292:09 pm -
1 stop9h 00m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 9/11![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:10 am -
2 stops9h 50m
Wed 11/115:30 am -
2 stops8h 15m
Deal found 9/8![Southwest logo]()
$489
This United Airlines deal was found by Cheapflights users on 9/11. 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 12/54:37 pm -
Nonstop3h 13m
Mon 12/75:55 am -
1 stop7h 42m
Deal found 9/11![United Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/96:00 am -
2 stops10h 44m
Sat 5/155:10 am -
2 stops7h 12m
Deal found 9/7![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 9/11. 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 10/233:25 pm -
2 stops8h 30m
Mon 10/264:15 pm -
2 stops6h 40m
Deal found 9/11![Southwest logo]()
$509
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:47 pm -
2 stops7h 10m
Wed 11/1112:06 pm -
2 stops10h 25m
Deal found 9/8![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:08 pm -
1 stop4h 57m
Sat 10/3112:32 pm -
2 stops9h 49m
Deal found 9/9![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 9/11. 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 10/265:30 pm -
1 stop7h 45m
Fri 10/307:15 am -
1 stop6h 35m
Deal found 9/11![Southwest logo]()
$516
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/146:00 am -
2 stops9h 29m
Sun 10/187:45 am -
1 stop5h 53m
Deal found 9/11![United Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:00 am -
1 stop7h 50m
Mon 12/214:45 pm -
1 stop5h 21m
Deal found 9/10![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:28 pm -
1 stop5h 28m
Fri 1/16:40 am -
1 stop7h 51m
Deal found 9/10![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:28 pm -
1 stop5h 49m
Wed 10/217:00 am -
2 stops8h 47m
Deal found 9/10![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/173:41 pm -
1 stop8h 09m
Wed 11/186:47 am -
1 stop6h 29m
Deal found 9/8![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:43 pm -
1 stop7h 37m
Sat 10/315:27 am -
2 stops9h 35m
Deal found 9/7![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:00 am -
1 stop5h 00m
Thu 10/2211:31 am -
2 stops11h 05m
Deal found 9/6![American Airlines logo]()
$793
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated September 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop6h 43m
Sat 10/33:25 pm -
1 stop7h 22m
Deal found 9/8![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:37 pm -
1 stop5h 54m
Tue 10/136:17 pm -
1 stop4h 42m
Deal found 9/8![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am -
1 stop5h 07m
Mon 10/128:00 pm -
Nonstop2h 40m
Deal found 9/10![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:37 pm -
1 stop6h 41m
Sat 10/172:58 pm -
1 stop7h 45m
Deal found 9/9![American Airlines logo]()
$325
This Cheapflightsfares deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:34 pm -
Nonstop3h 03m
Mon 10/198:25 am -
Nonstop2h 41m
Deal found 9/8![Sun Country Air logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/235:45 pm -
1 stop7h 12m
Sat 10/315:29 am -
1 stop6h 02m
Deal found 9/11![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop6h 43m
Sat 10/312:32 pm -
2 stops7h 49m
Deal found 9/11![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:35 am -
Nonstop3h 02m
Sat 10/316:15 pm -
Nonstop2h 33m
Deal found 9/11![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:27 pm -
2 stops8h 30m
Wed 10/285:29 am -
2 stops10h 28m
Deal found 9/10![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/295:08 pm -
1 stop6h 35m
Sun 11/18:00 am -
1 stop5h 16m
Deal found 9/11![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/11. 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 10/2912:42 pm -
2 stops10h 45m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 9/11![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:01 am -
1 stop7h 18m
Sun 11/17:00 am -
1 stop3h 57m
Deal found 9/7![Delta logo]()
$339
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 September 11, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:03 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Sun Country Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:12 pm -
1 stop15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:09 pm -
2 stops21h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:09 pm -
2 stops45h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:53 pm -
1 stop4h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:48 am -
2 stops29h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$164
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
1 stop4h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:09 pm -
2 stops21h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$172
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop4h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/135:35 pm -
3 stops21h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:31 pm -
2 stops22h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$177
This Sun Country Air deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:35 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Sun Country Air logo]()
$179
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 September 11, 2026.
Round-trip from | $301 (American Airlines) |
|---|---|
One-way from | $139 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $399 |
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 September 11, 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
Tue 12/1
4:53 pm-8:22 pm
1 stop4h 29m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 11/10
5:18 pm-10:18 pm
1 stop6h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 12/8
6:12 am-1:09 pm
1 stop7h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 11/12
11:39 am-6:22 pm
1 stop7h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 12/9
11:40 am-11:52 pm
2 stops13h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
PortlandMilwaukee
PWM Portland - MKE Milwaukee-Mitchell
PWMMKE
Portland
Fri 11/27
7:00 am-1:40 pm
1 stop7h 40m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$186
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 12/12
6:00 am-12:20 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/20
4:15 pm-9:43 pm
1 stop6h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 10/14
6:28 am-10:28 am
1 stop5h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 11/27
4:50 pm-8:17 pm
1 stop4h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$195
Showing 1-10 of 60 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-MSN
PWM-GRB
PWM-MKE
PWM-ATW
PWM-MSP
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-MSN
PWM-GRB
PWM-MKE
PWM-ATW
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 $586). 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 $391 and $500 in October.The cheapest round-trip price found within the last 5 days was $325 on American Airlines (Oct 15-Oct 17).
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 September 11, 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
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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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Search flights from Portland to Wisconsin by cabin class
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 September 11, 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 September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$198 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$432 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$343 | Average$399 | FlexibilityNo cancel fee | On-time63% |