$99+ Cheap flights from Portland, ME (PWM) to Wisconsin
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Sep 5 — Sep 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 August 6, 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 August 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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 8/2012:47 pm -
Nonstop3h 03m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/3![Sun Country Air logo]()
$227
This Sun Country Air deal was found by Cheapflights users on 8/5. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:28 pm -
Nonstop3h 03m
Sun 10/257:40 am -
Nonstop2h 44m
Deal found 8/5![Sun Country Air logo]()
$238
This United Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 9/53:45 pm -
1 stop6h 22m
Sun 9/65:50 pm -
Nonstop2h 33m
Deal found 8/3![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 8/4. 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.
Sat 9/52:57 pm -
1 stop7h 55m
Sun 9/66:59 am -
1 stop4h 03m
Deal found 8/4![Delta logo]()
$255
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
Fri 8/2112:51 pm -
Nonstop3h 03m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/3![Sun Country Air logo]()
$257
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/58:00 am -
1 stop5h 12m
Sun 9/66:00 am -
1 stop4h 46m
Deal found 8/2![American Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:00 am -
Nonstop3h 01m
Tue 9/152:10 pm -
Nonstop2h 44m
Deal found 8/4![United Airlines logo]()
$262
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:45 pm -
1 stop8h 13m
Mon 8/316:00 am -
1 stop6h 45m
Deal found 8/6![JetBlue logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:53 pm -
1 stop6h 35m
Mon 9/145:50 pm -
Nonstop2h 33m
Deal found 8/4![United Airlines logo]()
$272
This Cheapflightsfares deal was found by Cheapflights users on 8/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:55 pm -
Nonstop3h 03m
Mon 8/318:15 am -
Nonstop2h 41m
Deal found 8/1![Sun Country Air logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/227:00 am -
1 stop27h 01m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/1![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 9/115:29 pm -
1 stop5h 49m
Tue 9/156:00 am -
1 stop6h 16m
Deal found 8/4![Delta logo]()
$282
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 August 6, 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 August 6, 2026.
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 9/115:29 pm -
1 stop5h 49m
Tue 9/156:00 am -
1 stop6h 16m
Deal found 8/4![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 8/2. 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 10/297:30 pm -
1 stop5h 09m
Mon 11/26:18 pm -
Nonstop2h 33m
Deal found 8/2![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/95:38 pm -
1 stop7h 46m
Sun 9/135:05 pm -
1 stop5h 42m
Deal found 8/5![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 am -
2 stops6h 25m
Mon 10/264:35 pm -
2 stops6h 20m
Deal found 8/4![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am -
2 stops11h 51m
Thu 9/103:40 pm -
1 stop6h 49m
Deal found 8/5![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 8/3. 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 8/267:40 am -
Nonstop3h 03m
Fri 8/282:00 pm -
Nonstop2h 42m
Deal found 8/3![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Sat 10/245:45 pm -
1 stop7h 27m
Wed 10/285:29 am -
2 stops9h 14m
Deal found 8/5![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:30 am -
1 stop7h 29m
Mon 9/218:55 am -
1 stop6h 00m
Deal found 8/5![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:03 am -
1 stop5h 01m
Sun 9/66:30 am -
1 stop6h 59m
Deal found 8/4![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:05 pm -
2 stops8h 08m
Sun 9/135:43 am -
1 stop6h 22m
Deal found 8/1![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:52 pm -
1 stop5h 28m
Mon 11/25:27 am -
1 stop6h 35m
Deal found 8/5![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:05 pm -
2 stops8h 15m
Fri 9/1111:45 am -
2 stops9h 45m
Deal found 8/4![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:06 am -
2 stops8h 56m
Sun 9/1312:28 pm -
1 stop7h 55m
Deal found 8/4![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:09 pm -
1 stop7h 07m
Sat 8/295:37 am -
2 stops9h 56m
Deal found 8/1![American Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 8/2. 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 10/206:28 am -
2 stops7h 31m
Tue 10/206:00 pm -
1 stop5h 10m
Deal found 8/2![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 8/295:40 am -
2 stops8h 00m
Wed 9/210:30 am -
2 stops9h 40m
Deal found 8/2![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 8/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:03 am -
1 stop7h 35m
Tue 8/257:18 am -
1 stop6h 16m
Deal found 8/5![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/2. 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 10/205:28 pm -
1 stop6h 04m
Thu 10/2211:19 am -
2 stops11h 16m
Deal found 8/2![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/176:00 am -
1 stop6h 43m
Sun 9/208:02 am -
1 stop7h 22m
Deal found 8/2![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 8/296:03 am -
1 stop4h 57m
Wed 9/21:19 pm -
1 stop7h 04m
Deal found 8/2![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:02 am -
2 stops9h 27m
Tue 9/291:55 pm -
2 stops8h 22m
Deal found 8/6![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/43:06 pm -
2 stops9h 50m
Mon 9/145:05 pm -
1 stop5h 42m
Deal found 8/2![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 10/245:15 am -
2 stops7h 28m
Wed 10/2812:40 pm -
2 stops9h 41m
Deal found 8/2![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 8/3. 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 10/2212:42 pm -
2 stops12h 10m
Sat 10/248:29 am -
2 stops11h 31m
Deal found 8/3![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/112:03 pm -
1 stop5h 18m
Sun 9/132:48 pm -
1 stop7h 59m
Deal found 8/2![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/1. 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 11/44:47 pm -
2 stops7h 10m
Sat 11/75:14 am -
1 stop4h 36m
Deal found 8/1![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:58 am -
1 stop6h 39m
Mon 10/264:09 pm -
2 stops6h 50m
Deal found 8/4![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:52 pm -
1 stop6h 23m
Sun 10/185:51 am -
1 stop6h 11m
Deal found 8/5![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:45 pm -
1 stop5h 29m
Sun 9/66:30 am -
1 stop6h 59m
Deal found 8/4![United Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/56:02 am -
2 stops11h 08m
Tue 9/155:49 am -
1 stop6h 16m
Deal found 8/2![American Airlines logo]()
$434
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated August 6, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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 8/2012:47 pm -
Nonstop3h 03m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/3![Sun Country Air logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
Fri 8/2112:51 pm -
Nonstop3h 03m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/3![Sun Country Air logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/227:00 am -
1 stop27h 01m
Mon 8/248:05 am -
Nonstop2h 41m
Deal found 8/1![Multiple Airlines logo]()
$282
This Cheapflightsfares deal was found by Cheapflights users on 8/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:55 pm -
Nonstop3h 03m
Mon 8/318:15 am -
Nonstop2h 41m
Deal found 8/1![Sun Country Air logo]()
$277
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/282:45 pm -
1 stop8h 13m
Mon 8/316:00 am -
1 stop6h 45m
Deal found 8/6![JetBlue logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 9/53:45 pm -
1 stop6h 22m
Sun 9/65:50 pm -
Nonstop2h 33m
Deal found 8/3![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 8/4. 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.
Sat 9/52:57 pm -
1 stop7h 55m
Sun 9/66:59 am -
1 stop4h 03m
Deal found 8/4![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/58:00 am -
1 stop5h 12m
Sun 9/66:00 am -
1 stop4h 46m
Deal found 8/2![American Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:00 am -
Nonstop3h 01m
Tue 9/152:10 pm -
Nonstop2h 44m
Deal found 8/4![United Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:53 pm -
1 stop6h 35m
Mon 9/145:50 pm -
Nonstop2h 33m
Deal found 8/4![United Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 8/4. 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.
Fri 9/115:29 pm -
1 stop5h 49m
Tue 9/156:00 am -
1 stop6h 16m
Deal found 8/4![Delta logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 9/1712:03 pm -
Nonstop3h 03m
Mon 9/219:28 am -
3 stops29h 56m
Deal found 8/3![Multiple Airlines logo]()
$283
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 August 6, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Sun Country Air deal was found by Cheapflights users on 8/2. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:03 pm -
Nonstop3h 03m
Deal found 8/2![Sun Country Air logo]()
$99
This Delta deal was found by Cheapflights users on 8/3. 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.
Sat 9/512:10 pm -
1 stop8h 03m
Deal found 8/3![Delta logo]()
$128
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
1 stop4h 58m
Deal found 8/3![JetBlue logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Mon 8/317:00 am -
2 stops12h 02m
Deal found 8/1![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:31 pm -
2 stops21h 53m
Deal found 8/2![Multiple Airlines logo]()
$144
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 9/196:00 am -
Nonstop2h 57m
Deal found 8/2![United Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/296:30 am -
Nonstop3h 08m
Deal found 8/2![American Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/47:00 am -
2 stops31h 43m
Deal found 8/3![Multiple Airlines logo]()
$150
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 9/226:00 am -
1 stop6h 43m
Deal found 8/5![American Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:00 am -
2 stops29h 50m
Deal found 8/5![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am -
1 stop7h 35m
Deal found 8/1![Delta logo]()
$155
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:40 pm -
1 stop8h 18m
Deal found 8/3![JetBlue logo]()
$157
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 August 6, 2026.
Round-trip from | $227 (Cheapflightsfares) |
|---|---|
One-way from | $99 (Sun Country Air) |
Popular in | August |
Cheapest in | November |
Average price | $1,117 |
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 2,558,603 searches. Data last updated August 6, 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
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 9/11
5:29 pm-10:18 pm
1 stop5h 49m
Chicago O'Hare Intl
Tue 9/15
6:00 am-1:16 pm
1 stop6h 16m
$282
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 9/5
6:00 am-4:51 pm
2 stops11h 51m
Chicago O'Hare Intl
Thu 9/10
3:40 pm-11:29 pm
1 stop6h 49m
$287
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/29
7:30 pm-11:39 pm
1 stop5h 09m
Chicago O'Hare Intl
Mon 11/2
6:18 pm-9:51 pm
Nonstop2h 33m
$299
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 9/9
6:30 am-12:59 pm
1 stop7h 29m
Chicago O'Hare Intl
Mon 9/21
8:55 am-3:55 pm
1 stop6h 00m
$309
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/29
1:52 pm-6:20 pm
1 stop5h 28m
Chicago O'Hare Intl
Mon 11/2
5:27 am-1:02 pm
1 stop6h 35m
$309
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/20
6:28 am-12:59 pm
2 stops7h 31m
Chicago O'Hare Intl
Tue 10/20
6:00 pm-12:10 am
1 stop5h 10m
$314
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/20
5:28 pm-10:32 pm
1 stop6h 04m
Chicago O'Hare Intl
Thu 10/22
11:19 am-11:35 pm
2 stops11h 16m
$314
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 9/26
6:02 am-2:29 pm
2 stops9h 27m
Chicago O'Hare Intl
Tue 9/29
1:55 pm-11:17 pm
2 stops8h 22m
$319
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/22
12:42 pm-11:52 pm
2 stops12h 10m
Chicago O'Hare Intl
Sat 10/24
8:29 am-9:00 pm
2 stops11h 31m
$319
Quickest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 8/26
7:40 am-9:43 am
Nonstop3h 03m
Chicago O'Hare Intl
Fri 8/28
2:00 pm-5:42 pm
Nonstop2h 42m
$322
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-ORD
PWM-CWA
PWM-MKE
PWM-ATW
PWM-MSN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Wisconsin
PWM-USWI
PWM-ORD
PWM-CWA
PWM-MKE
PWM-ATW
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, November is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $328). Flying from Portland, Maine to Wisconsin in December is currently the most expensive (average of $583). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 August 6, 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
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 6, 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 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$398 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$324 | Average$399 | FlexibilityNo cancel fee | On-time63% |