$99+ Cheap flights from Wisconsin to Portland, ME (PWM)
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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Oct 12 — Oct 191
Round-trip
1 adult, Economy
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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 Wisconsin to PortlandExplore the most affordable flight options available from Wisconsin to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
Explore the most affordable flight options available from Wisconsin to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
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.
Tue 10/136:17 pm -
1 stop4h 42m
Wed 10/215:37 pm -
1 stop6h 48m
Deal found 9/9![American Airlines logo]()
$301
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.
Tue 10/1311:14 am -
2 stops11h 56m
Wed 10/2112:42 pm -
2 stops11h 21m
Deal found 9/9![Delta logo]()
$311
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 10/75:31 pm -
1 stop5h 05m
Fri 10/165:37 pm -
1 stop5h 54m
Deal found 9/7![American Airlines logo]()
$315
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.
Sat 10/172:46 pm -
1 stop7h 57m
Thu 10/225:45 pm -
1 stop7h 27m
Deal found 9/9![American Airlines logo]()
$319
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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
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.
Mon 10/198:25 am -
Nonstop2h 41m
Wed 10/285:09 pm -
2 stops22h 11m
Deal found 9/7![Multiple Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:36 am -
1 stop5h 11m
Wed 10/146:28 am -
1 stop7h 10m
Deal found 9/8![Delta logo]()
$325
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.
Sat 10/176:00 am -
2 stops9h 47m
Sat 10/246:00 am -
2 stops9h 14m
Deal found 9/7![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 10/2410:00 am -
1 stop7h 43m
Tue 10/275:08 pm -
1 stop7h 09m
Deal found 9/11![United Airlines logo]()
$329
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.
Mon 10/55:31 pm -
1 stop5h 05m
Thu 10/156:00 am -
1 stop6h 54m
Deal found 9/7![American Airlines logo]()
$329
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.
Wed 10/77:18 am -
1 stop6h 20m
Wed 10/145:15 am -
2 stops7h 15m
Deal found 9/10![United Airlines logo]()
$330
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.
Thu 10/2911:31 am -
2 stops11h 28m
Sat 10/317:00 am -
1 stop5h 00m
Deal found 9/8![American Airlines logo]()
$334
Best flights from Wisconsin to PortlandDiscover carefully curated flight deals from Wisconsin to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 2026.
Discover carefully curated flight deals from Wisconsin to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
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.
Sat 10/172:46 pm -
1 stop7h 57m
Sat 10/245:30 am -
2 stops9h 44m
Deal found 9/7![American Airlines logo]()
$324
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 10/1311:14 am -
2 stops11h 56m
Wed 10/2112:42 pm -
2 stops11h 21m
Deal found 9/11![Delta logo]()
$331
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.
Tue 10/201:40 pm -
2 stops8h 00m
Wed 10/2812:55 pm -
2 stops10h 55m
Deal found 9/7![Southwest logo]()
$419
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 10/75:00 am -
1 stop4h 40m
Wed 10/146:55 pm -
1 stop5h 42m
Deal found 9/9![United 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.
Thu 10/2911:31 am -
2 stops11h 28m
Sat 10/316:00 am -
2 stops11h 12m
Deal found 9/8![American Airlines logo]()
$339
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.
Tue 10/62:59 pm -
1 stop7h 36m
Thu 10/156:01 am -
1 stop8h 53m
Deal found 9/8![Delta logo]()
$348
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 10/2410:00 am -
1 stop7h 43m
Tue 10/275:08 pm -
1 stop7h 09m
Deal found 9/11![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:09 am -
2 stops8h 52m
Sat 10/316:01 am -
1 stop7h 12m
Deal found 9/10![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:45 pm -
1 stop5h 01m
Sat 10/245:08 pm -
1 stop7h 09m
Deal found 9/7![United Airlines logo]()
$339
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.
Mon 11/92:50 pm -
1 stop8h 00m
Fri 11/1311:10 am -
2 stops9h 50m
Deal found 9/7![Southwest logo]()
$420
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 10/288:29 am -
2 stops7h 18m
Sat 10/314:47 pm -
2 stops8h 10m
Deal found 9/11![Delta logo]()
$387
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 9/305:05 pm -
1 stop5h 42m
Wed 10/74:27 pm -
2 stops8h 51m
Deal found 9/8![American Airlines logo]()
$435
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 10/264:15 pm -
2 stops6h 40m
Sat 10/317:20 am -
2 stops9h 40m
Deal found 9/11![Southwest logo]()
$439
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 10/2312:28 pm -
2 stops10h 00m
Tue 10/278:32 am -
1 stop6h 24m
Deal found 9/10![United Airlines logo]()
$379
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 9/221:55 pm -
2 stops9h 01m
Wed 10/281:52 pm -
2 stops7h 38m
Deal found 9/10![Delta logo]()
$397
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.
Tue 9/225:49 am -
2 stops8h 52m
Sat 9/266:00 am -
2 stops11h 35m
Deal found 9/7![American Airlines logo]()
$466
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.
Sat 10/248:10 am -
1 stop5h 28m
Wed 10/288:49 am -
2 stops11h 18m
Deal found 9/9![United Airlines logo]()
$386
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.
Sat 10/176:00 am -
2 stops8h 55m
Sat 10/2412:45 pm -
2 stops8h 20m
Deal found 9/7![Southwest logo]()
$475
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:00 pm -
1 stop5h 01m
Sun 11/811:55 am -
Nonstop3h 07m
Deal found 9/9![Delta logo]()
$399
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.
Tue 9/222:47 pm -
1 stop5h 36m
Sat 9/267:58 am -
1 stop8h 06m
Deal found 9/9![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:20 am -
2 stops8h 42m
Tue 10/201:52 pm -
1 stop7h 51m
Deal found 9/10![Delta logo]()
$402
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.
Sat 10/173:55 pm -
1 stop5h 20m
Mon 10/265:20 am -
2 stops7h 00m
Deal found 9/11![Southwest logo]()
$504
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 10/2211:31 am -
2 stops11h 28m
Sat 10/246:00 am -
2 stops11h 12m
Deal found 9/9![American Airlines logo]()
$535
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 1/266:15 am -
1 stop7h 27m
Sat 1/303:15 pm -
2 stops8h 35m
Deal found 9/8![United Airlines logo]()
$404
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 10/176:20 am -
2 stops8h 42m
Thu 10/225:28 pm -
1 stop5h 49m
Deal found 9/7![Delta logo]()
$406
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 11/127:00 am -
1 stop7h 16m
Mon 11/164:50 pm -
1 stop5h 02m
Deal found 9/10![Delta logo]()
$409
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 11/138:15 am -
1 stop5h 01m
Sun 11/155:08 pm -
1 stop6h 59m
Deal found 9/10![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/29:20 am -
2 stops7h 53m
Wed 2/37:23 am -
2 stops7h 38m
Deal found 9/10![United Airlines logo]()
$415
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.
Sun 10/118:39 am -
1 stop6h 23m
Wed 10/146:28 am -
2 stops7h 31m
Deal found 9/8![Delta logo]()
$419
Last-minute flights from Wisconsin to PortlandDiscover last-minute flight deals from Wisconsin to Portland. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Portland. Data last updated September 12, 2026 and is based on user searches.
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.
Mon 10/55:31 pm -
1 stop5h 05m
Thu 10/156:00 am -
1 stop6h 54m
Deal found 9/7![American Airlines logo]()
$329
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 10/75:31 pm -
1 stop5h 05m
Fri 10/165:37 pm -
1 stop5h 54m
Deal found 9/7![American Airlines logo]()
$315
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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:36 am -
1 stop5h 11m
Wed 10/146:28 am -
1 stop7h 10m
Deal found 9/8![Delta logo]()
$325
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.
Wed 10/77:18 am -
1 stop6h 20m
Wed 10/145:15 am -
2 stops7h 15m
Deal found 9/10![United Airlines logo]()
$330
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.
Tue 10/136:17 pm -
1 stop4h 42m
Wed 10/215:37 pm -
1 stop6h 48m
Deal found 9/9![American Airlines logo]()
$301
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.
Tue 10/1311:14 am -
2 stops11h 56m
Wed 10/2112:42 pm -
2 stops11h 21m
Deal found 9/9![Delta logo]()
$311
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.
Sat 10/172:46 pm -
1 stop7h 57m
Thu 10/225:45 pm -
1 stop7h 27m
Deal found 9/9![American Airlines logo]()
$319
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.
Sat 10/176:00 am -
2 stops9h 47m
Sat 10/246:00 am -
2 stops9h 14m
Deal found 9/7![American Airlines logo]()
$329
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.
Mon 10/198:25 am -
Nonstop2h 41m
Wed 10/285:09 pm -
2 stops22h 11m
Deal found 9/7![Multiple Airlines logo]()
$322
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 10/2410:00 am -
1 stop7h 43m
Tue 10/275:08 pm -
1 stop7h 09m
Deal found 9/11![United 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.
Thu 10/2911:31 am -
2 stops11h 28m
Sat 10/317:00 am -
1 stop5h 00m
Deal found 9/8![American Airlines logo]()
$334
One-way flights from Wisconsin to PortlandSearch for one-way flight options from Wisconsin to Portland. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
Search for one-way flight options from Wisconsin to Portland. Find affordable one-way fares based on user searches. Data last updated September 12, 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.
Mon 10/198:25 am -
Nonstop2h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Sun Country Air logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:33 am -
2 stops22h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:01 pm -
2 stops45h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$146
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 11/43:01 pm -
2 stops45h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:36 pm -
2 stops45h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:01 pm -
2 stops41h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$153
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.
Mon 10/199:33 am -
2 stops46h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:01 pm -
2 stops24h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$155
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.
Sat 11/148:10 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:11 am -
2 stops33h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$167
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.
Sat 11/149:23 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$168
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:18 pm -
Nonstop2h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$169
Find flight deals from Wisconsin to Portland
Keep the following information in mind while searching for Wisconsin to Portland flight deals. Data was last updated September 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (American Airlines) |
One-way from | $99 (Cheapflightsfares) |
Popular in | December |
Cheapest in | January |
Average price | $426 |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 12, 2026.
Use the filters below to find and compare flights from Wisconsin to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Sat 11/14
9:23 am-7:02 pm
2 stops8h 39m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$168
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 10/28
6:18 pm-9:51 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 10/6
6:00 pm-12:10 am
1 stop5h 10m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 10/28
5:27 am-1:02 pm
1 stop6h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 12/9
3:59 pm-11:34 pm
1 stop6h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 12/5
7:00 am-1:07 pm
1 stop5h 07m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sun 11/8
6:00 pm-9:08 am
1 stop14h 08m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$181
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Mon 10/19
1:25 pm-11:35 pm
2 stops9h 10m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 10/1
6:10 am-3:55 pm
2 stops8h 45m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Fri 10/2
2:20 pm-9:46 pm
1 stop6h 26m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Wisconsin with our price prediction graph.
MSP-PWM
MKE-PWM
ORD-PWM
MSN-PWM
GRB-PWM
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 Wisconsin to Portland
USWI-PWM
MSP-PWM
MKE-PWM
ORD-PWM
MSN-PWM
What is the cheapest month to book a flight from Wisconsin to Portland, Maine?
Currently, January is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $340). Flying from Wisconsin to Portland, Maine in December is currently the most expensive (average of $628). 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 Wisconsin to Portland, Maine?
Airfare is below average for this route at the moment.
Wisconsin to Portland, Maine flights typically cost between $360 and $457 in October.The cheapest round-trip price found within the last 5 days was $325 on Delta (Oct 7-Oct 14).
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsNorth Conway
Lewiston
Brunswick
Conway
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Wisconsin to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Portland by cabin class
Find flights from Wisconsin to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Portland flights
Browse other Wisconsin and Portland flight options. Last updated on September 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 12, 2026.
Wisconsin to Portland flights
Consider these flights traveling from Wisconsin to Portland.
Top 4 airlines flying from Wisconsin to Portland
Discover the top 4 airlines that operate flights from Wisconsin to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$420 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$290 | Average$474 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$386 | Average$558 | FlexibilityNo cancel fee | On-time63% |