$109+ 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 5 — Oct 121
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 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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
Nonstop2h 57m
Tue 10/2010:00 am -
2 stops8h 24m
Deal found 8/31![United Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:08 pm -
1 stop6h 59m
Thu 11/128:15 am -
1 stop5h 01m
Deal found 9/3![United Airlines logo]()
$315
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:18 pm -
Nonstop3h 03m
Sun 9/2712:15 pm -
Nonstop2h 41m
Deal found 8/31![Sun Country Air logo]()
$316
This Delta deal was found by Cheapflights users on 9/1. 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.
Tue 10/275:28 pm -
1 stop4h 56m
Sat 10/318:00 am -
1 stop4h 51m
Deal found 9/1![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/225:45 pm -
1 stop7h 27m
Mon 10/266:17 pm -
1 stop4h 42m
Deal found 9/2![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/55:10 pm -
1 stop7h 20m
Mon 11/97:55 am -
2 stops7h 35m
Deal found 8/31![Southwest logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Thu 9/1712:03 pm -
Nonstop3h 03m
Tue 9/2212:45 pm -
3 stops26h 49m
Deal found 9/1![Multiple Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 -
2 stops7h 35m
Sun 10/187:36 am -
1 stop7h 07m
Deal found 9/5![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 10/245:38 pm -
2 stops7h 19m
Wed 10/2811:33 am -
1 stop4h 31m
Deal found 9/2![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/15:05 pm -
2 stops8h 19m
Mon 10/54:42 pm -
1 stop5h 58m
Deal found 8/31![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/305:38 pm -
Nonstop3h 21m
Wed 10/77:59 pm -
Nonstop2h 44m
Deal found 8/31![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/157:00 am -
Nonstop3h 04m
Tue 10/208:00 pm -
Nonstop2h 40m
Deal found 9/2![American Airlines logo]()
$337
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
Nonstop2h 57m
Tue 10/2010:00 am -
2 stops8h 24m
Deal found 8/31![United Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/146:00 am -
1 stop6h 54m
Thu 10/225:31 pm -
1 stop5h 05m
Deal found 8/31![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 9/3. 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 10/226:01 am -
1 stop8h 53m
Tue 10/272:59 pm -
1 stop7h 02m
Deal found 9/3![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/55:10 pm -
1 stop7h 20m
Mon 11/97:55 am -
2 stops7h 35m
Deal found 8/31![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:47 pm -
1 stop4h 19m
Mon 11/95:55 pm -
1 stop4h 26m
Deal found 9/2![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 10/245:38 pm -
2 stops7h 19m
Wed 10/2811:33 am -
1 stop4h 31m
Deal found 9/2![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/1. 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 9/3011:35 am -
Nonstop3h 02m
Wed 10/711:04 am -
Nonstop2h 34m
Deal found 9/1![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 pm -
2 stops7h 24m
Mon 10/54:42 pm -
1 stop5h 58m
Deal found 9/3![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/125:08 pm -
Nonstop2h 57m
Mon 11/165:59 am -
1 stop7h 28m
Deal found 8/31![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:50 am -
1 stop7h 07m
Mon 9/281:30 pm -
2 stops9h 26m
Deal found 9/2![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Wed 11/43:25 pm -
2 stops8h 30m
Mon 11/911:00 am -
2 stops11h 50m
Deal found 8/31![Southwest logo]()
$419
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 1/84:00 pm -
2 stops9h 25m
Sun 1/1011:30 am -
2 stops10h 16m
Deal found 9/4![American Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 stops8h 37m
Thu 10/224:10 pm -
1 stop4h 36m
Deal found 8/31![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/266:27 am -
2 stops7h 12m
Mon 11/304:01 pm -
1 stop6h 20m
Deal found 9/4![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/55:10 pm -
2 stops7h 10m
Tue 11/1010:55 am -
2 stops9h 50m
Deal found 8/31![Southwest logo]()
$419
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/285:08 pm -
1 stop4h 57m
Sat 10/316:25 am -
1 stop6h 51m
Deal found 9/1![United Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/25:38 pm -
1 stop7h 39m
Thu 10/86:17 pm -
1 stop4h 42m
Deal found 9/2![American Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop5h 38m
Mon 9/281:30 pm -
2 stops9h 26m
Deal found 9/2![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 9/2. 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 10/265:20 am -
2 stops9h 50m
Thu 10/296:15 am -
1 stop5h 10m
Deal found 9/2![Southwest logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Mon 9/216:00 am -
1 stop4h 40m
Sun 9/276:49 am -
2 stops6h 49m
Deal found 9/1![United Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/15:05 pm -
2 stops8h 08m
Sun 10/44:04 pm -
1 stop6h 43m
Deal found 9/2![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 9/1. 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.
Thu 12/34:00 pm -
1 stop5h 41m
Sat 12/56:00 am -
1 stop5h 04m
Deal found 9/1![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 9/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:25 am -
1 stop5h 25m
Thu 12/31:50 pm -
1 stop6h 55m
Deal found 9/3![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 10/15:08 pm -
1 stop7h 11m
Mon 10/51:17 pm -
1 stop7h 29m
Deal found 9/2![United Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/15:05 pm -
2 stops8h 08m
Mon 10/52:46 pm -
2 stops6h 45m
Deal found 9/2![American Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 9/1. 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.
Tue 12/14:53 pm -
1 stop5h 05m
Sun 12/67:00 am -
1 stop7h 20m
Deal found 9/1![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 9/1. 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.
Thu 12/36:00 am -
1 stop7h 07m
Mon 12/74:28 pm -
1 stop6h 25m
Deal found 9/1![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop5h 07m
Tue 10/279:33 am -
2 stops12h 48m
Deal found 9/3![United Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
2 stops11h 13m
Wed 10/76:00 am -
1 stop6h 12m
Deal found 8/31![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:50 am -
2 stops10h 08m
Wed 11/186:00 am -
2 stops7h 27m
Deal found 9/3![United Airlines logo]()
$415
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated September 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Thu 9/1712:03 pm -
Nonstop3h 03m
Tue 9/2212:45 pm -
3 stops26h 49m
Deal found 9/1![Multiple Airlines logo]()
$331
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:18 pm -
Nonstop3h 03m
Sun 9/2712:15 pm -
Nonstop2h 41m
Deal found 8/31![Sun Country Air logo]()
$316
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/305:38 pm -
Nonstop3h 21m
Wed 10/77:59 pm -
Nonstop2h 44m
Deal found 8/31![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/15:05 pm -
2 stops8h 19m
Mon 10/54:42 pm -
1 stop5h 58m
Deal found 8/31![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/146:00 am -
1 stop6h 54m
Thu 10/225:31 pm -
1 stop5h 05m
Deal found 8/31![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 -
2 stops7h 35m
Sun 10/187:36 am -
1 stop7h 07m
Deal found 9/5![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/157:00 am -
Nonstop3h 04m
Tue 10/208:00 pm -
Nonstop2h 40m
Deal found 9/2![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 10/175:38 pm -
2 stops7h 34m
Mon 10/266:17 pm -
1 stop4h 42m
Deal found 9/2![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 -
Nonstop2h 57m
Tue 10/2010:00 am -
2 stops8h 24m
Deal found 8/31![United Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/225:45 pm -
1 stop7h 27m
Mon 10/266:17 pm -
1 stop4h 42m
Deal found 9/2![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 10/245:38 pm -
2 stops7h 19m
Wed 10/2811:33 am -
1 stop4h 31m
Deal found 9/2![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/1. 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.
Tue 10/276:28 am -
1 stop7h 10m
Wed 11/47:15 am -
1 stop3h 42m
Deal found 9/1![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 September 5, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/2. 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 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 9/2![Sun Country Air logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:18 pm -
Nonstop3h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Sun Country Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Wed 12/27:12 pm -
1 stop15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 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 9/3![Multiple Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Tue 9/295:08 pm -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![United Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
2 stops26h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 9/266:30 am -
Nonstop3h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/4![Multiple Airlines logo]()
$170
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 9/295:38 pm -
Nonstop3h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Wed 9/307:00 am -
3 stops25h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$175
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Mon 9/286:00 am -
Nonstop2h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![United Airlines logo]()
$175
This Delta deal was found by Cheapflights users on 9/1. 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.
Wed 3/311:25 am -
1 stop5h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Delta 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 5, 2026.
Round-trip from | $306 (American Airlines) |
|---|---|
One-way from | $109 (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 5, 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 9/29
5:15 am-11:30 am
2 stops7h 15m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
Quickest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 9/29
5:08 pm-7:05 pm
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 9/12
8:00 am-10:03 am
Nonstop3h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$169
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 11/3
5:50 am-11:47 am
1 stop6h 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
Wed 10/14
6:00 am-10:53 am
1 stop5h 53m
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 10/14
6:04 am-4:58 pm
2 stops11h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 12/2
6:12 am-2:49 pm
2 stops9h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 11/4
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
Fri 11/6
4:47 pm-8:30 pm
1 stop4h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 11/13
3:41 pm-10:18 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$199
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-MSP
PWM-ORD
PWM-MKE
PWM-MSN
PWM-ATW
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-MSP
PWM-ORD
PWM-MKE
PWM-MSN
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 Delta (Oct 27-Oct 31).
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 5, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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 5, 2026.
Popular flight searches
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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 5, 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% |