$88+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 1 — May 81
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 April 1, 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 April 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/188:35 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/30![Sun Country Air logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:16 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Thu 10/87:55 am
MSP
- PWM
Nonstop2h 44m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$217
This Expedia deal was found by Cheapflights users on 4/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
- ORD
1 stop8h 00m
JetBlue
Tue 6/166:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Deal found 4/1![JetBlue logo]()
$239
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
- ORD
1 stop8h 00m
JetBlue
Wed 6/176:00 am
ORD
- PWM
1 stop6h 35m
JetBlue
Deal found 4/1![JetBlue logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 7/198:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/28![Sun Country Air logo]()
$257
This Sun Country Air deal was found by Cheapflights users on 3/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$264
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:16 am
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/188:35 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/29![Sun Country Air logo]()
$267
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:07 am
PWM
- ORD
Nonstop3h 10m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/27![American Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:51 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 5/2410:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 3/28![United Airlines logo]()
$269
This Super.com deal was found by Cheapflights users on 4/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 6/297:40 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 4/1![Sun Country Air logo]()
$277
This American Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
PWM
- ORD
Nonstop3h 01m
American Airlines
Wed 8/2611:30 am
ORD
- PWM
Nonstop2h 30m
American Airlines
Deal found 3/28![American Airlines logo]()
$278
This KAYAK deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:40 pm
PWM
- ORD
1 stop8h 15m
JetBlue
Tue 7/286:00 am
ORD
- PWM
1 stop5h 21m
JetBlue
Deal found 3/30![JetBlue logo]()
$284
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 April 1, 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 April 1, 2026.
This Sun Country Air deal was found by Cheapflights users on 3/31. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$264
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:33 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Mon 5/46:55 am
ORD
- PWM
Nonstop2h 28m
United Airlines
Deal found 3/28![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 3/31. 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.
Tue 5/1211:03 am
PWM
- ORD
1 stop8h 04m
Delta
Tue 5/197:00 am
ORD
- PWM
1 stop4h 00m
Delta
Deal found 3/31![Delta logo]()
$289
This JetBlue deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:40 pm
PWM
- ORD
1 stop8h 15m
JetBlue
Tue 9/16:00 am
ORD
- PWM
1 stop5h 21m
JetBlue
Deal found 3/29![JetBlue logo]()
$321
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/146:01 pm
PWM
- GRB
1 stop6h 34m
American Airlines
Sat 5/165:24 pm
GRB
- PWM
1 stop4h 58m
American Airlines
Deal found 3/31![American Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:50 pm
PWM
- MSP
2 stops10h 30m
Southwest
Mon 5/115:20 am
MSP
- PWM
2 stops7h 50m
Southwest
Deal found 4/1![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/294:51 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 5/316:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/29![United Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Fri 9/115:05 pm
PWM
- ORD
Nonstop2h 55m
United Airlines
Sun 9/136:25 pm
ORD
- PWM
Nonstop2h 36m
United Airlines
Deal found 3/31![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:05 am
PWM
- ORD
2 stops9h 24m
Delta
Tue 5/267:00 am
ORD
- PWM
1 stop4h 00m
Delta
Deal found 3/30![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:50 pm
PWM
- MSN
1 stop7h 04m
United Airlines
Sat 5/94:02 pm
MSN
- PWM
1 stop4h 17m
United Airlines
Deal found 3/30![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:00 pm
PWM
- MSP
1 stop8h 25m
Delta
Mon 8/317:00 am
MSP
- PWM
Nonstop2h 49m
Delta
Deal found 3/30![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:30 pm
PWM
- ATW
1 stop5h 01m
American Airlines
Mon 7/203:58 pm
ATW
- PWM
1 stop5h 38m
American Airlines
Deal found 3/29![American Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 pm
PWM
- MKE
1 stop7h 15m
Southwest
Sun 5/34:45 pm
MKE
- PWM
2 stops6h 20m
Southwest
Deal found 3/29![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 6/186:00 am
PWM
- MSN
1 stop4h 59m
United Airlines
Tue 6/236:30 am
MSN
- PWM
2 stops7h 04m
United Airlines
Deal found 3/27![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/182:38 pm
PWM
- MKE
1 stop8h 14m
Delta
Sun 5/247:15 am
MKE
- PWM
1 stop5h 43m
Delta
Deal found 3/28![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 8/151:14 pm
PWM
- ATW
2 stops11h 13m
American Airlines
Sat 8/223:40 pm
ATW
- PWM
1 stop6h 21m
American Airlines
Deal found 3/31![American Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 8/295:05 pm
PWM
- ORD
Nonstop2h 55m
United Airlines
Tue 9/110:55 am
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/27![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/143:55 pm
PWM
- MKE
2 stops6h 50m
Southwest
Thu 4/163:30 pm
MKE
- PWM
1 stop6h 55m
Southwest
Deal found 3/30![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 3/31. 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.
Sat 9/193:00 pm
PWM
- MSP
1 stop8h 25m
Delta
Mon 9/217:00 am
MSP
- PWM
Nonstop2h 49m
Delta
Deal found 3/31![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
PWM
- MSP
1 stop7h 12m
United Airlines
Wed 6/101:08 pm
MSP
- PWM
1 stop7h 43m
United Airlines
Deal found 3/29![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:00 pm
PWM
- MSP
1 stop8h 25m
Delta
Mon 9/217:00 am
MSP
- PWM
Nonstop2h 49m
Delta
Deal found 3/28![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 5/226:00 am
PWM
- MSP
1 stop7h 12m
United Airlines
Mon 5/256:00 am
MSP
- PWM
1 stop7h 26m
United Airlines
Deal found 4/1![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:29 am
PWM
- CWA
2 stops9h 31m
American Airlines
Wed 5/276:00 am
CWA
- PWM
2 stops10h 07m
American Airlines
Deal found 3/29![American Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:55 pm
PWM
- ATW
2 stops10h 38m
Delta
Tue 5/1912:32 pm
ATW
- PWM
2 stops9h 46m
Delta
Deal found 3/28![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/135:30 am
PWM
- ORD
1 stop5h 07m
United Airlines
Tue 5/1910:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 3/31![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:51 pm
PWM
- MSN
2 stops9h 00m
Delta
Mon 4/272:57 pm
MSN
- PWM
1 stop7h 27m
Delta
Deal found 3/30![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Sun 7/126:08 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/29![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 3/31. 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 7/75:15 am
PWM
- ORD
1 stop7h 38m
United Airlines
Sun 7/126:08 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/31![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 5/84:50 pm
PWM
- MSP
1 stop6h 06m
United Airlines
Mon 5/113:25 pm
MSP
- PWM
2 stops7h 34m
United Airlines
Deal found 4/1![United Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:01 pm
PWM
- CWA
1 stop6h 47m
American Airlines
Mon 4/202:13 pm
CWA
- PWM
2 stops8h 14m
American Airlines
Deal found 3/29![American Airlines logo]()
$780
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated April 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Mon 4/207:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/30![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 4/187:23 pm
PWM
- ORD
1 stop5h 35m
American Airlines
Tue 4/218:35 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/31![American Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:29 am
PWM
- ORD
1 stop12h 32m
Multiple Airlines
Mon 5/47:33 pm
ORD
- PWM
2 stops43h 43m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 3/31. 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.
Mon 5/44:43 pm
PWM
- ORD
2 stops8h 16m
Delta
Tue 5/511:00 am
ORD
- PWM
1 stop3h 57m
Delta
Deal found 3/31![Delta logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:29 am
PWM
- ORD
1 stop12h 37m
Multiple Airlines
Tue 5/59:42 pm
ORD
- PWM
2 stops17h 34m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:50 pm
PWM
- MSN
1 stop7h 04m
United Airlines
Sat 5/94:02 pm
MSN
- PWM
1 stop4h 17m
United Airlines
Deal found 3/30![United Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:30 am
PWM
- MSP
1 stop6h 23m
United Airlines
Tue 5/123:25 pm
MSP
- PWM
1 stop4h 54m
United Airlines
Deal found 3/30![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:56 am
PWM
- ORD
1 stop7h 02m
American Airlines
Sat 5/161:54 pm
ORD
- PWM
1 stop7h 52m
American Airlines
Deal found 3/29![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:51 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 5/2410:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 3/28![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Fri 5/225:57 pm
PWM
- ORD
1 stop7h 02m
American Airlines
Mon 5/256:55 am
ORD
- PWM
1 stop5h 43m
American Airlines
Deal found 3/31![American Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Multiple Airlines
Mon 6/11:40 pm
MSP
- PWM
2 stops23h 51m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 5/295:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Sun 5/316:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/1![United Airlines logo]()
$303
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 April 1, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:18 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 3/28![Sun Country Air logo]()
$98
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
PWM
- ORD
1 stop5h 18m
JetBlue
Deal found 3/31![JetBlue logo]()
$107
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:37 pm
PWM
- ORD
1 stop9h 21m
JetBlue
Deal found 4/1![JetBlue logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:57 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 7/412:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/1![Sun Country Air logo]()
$119
This Trip.com deal was found by Cheapflights users on 4/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:35 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Deal found 4/1![Sun Country Air logo]()
$123
This KAYAK deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:36 pm
PWM
- ORD
1 stop9h 22m
JetBlue
Deal found 3/30![JetBlue logo]()
$124
This KAYAK deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:25 pm
PWM
- ORD
1 stop7h 19m
JetBlue
Deal found 3/28![JetBlue logo]()
$133
This American Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Deal found 3/30![American Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/275:06 pm
PWM
- ORD
3 stops42h 17m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$136
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:36 pm
PWM
- ORD
1 stop9h 22m
JetBlue
Deal found 3/31![JetBlue logo]()
$138
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 April 1, 2026.
Round-trip from | $207 (Cheapflightsfares) |
|---|---|
One-way from | $88 (Kiwi.com) |
Popular in | September |
Cheapest in | November |
Average price | $547 |
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 April 1, 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
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Thu 7/16
12:58 pm-3:06 pm
Nonstop3h 08m
Minneapolis St Paul
Mon 7/20
8:40 am-12:19 pm
Nonstop2h 39m
$264
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 4/27
6:33 pm-8:43 pm
Nonstop3h 10m
Chicago O'Hare Intl
Mon 5/4
6:55 am-10:23 am
Nonstop2h 28m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/29
4:51 pm-6:51 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/31
6:18 pm-9:51 pm
Nonstop2h 33m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 9/11
5:05 pm-7:00 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sun 9/13
6:25 pm-10:01 pm
Nonstop2h 36m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 5/12
11:03 am-6:07 pm
1 stop8h 04m
Chicago O'Hare Intl
Tue 5/19
7:00 am-12:00 pm
1 stop4h 00m
$289
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 5/6
4:50 pm-10:54 pm
1 stop7h 04m
Madison Truax Field
Sat 5/9
4:02 pm-9:19 pm
1 stop4h 17m
$291
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 8/29
2:40 pm-9:55 pm
1 stop8h 15m
Chicago O'Hare Intl
Tue 9/1
6:00 am-12:21 pm
1 stop5h 21m
$321
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/23
8:05 am-4:29 pm
2 stops9h 24m
Chicago O'Hare Intl
Tue 5/26
7:00 am-12:00 pm
1 stop4h 00m
$340
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Wed 8/26
3:00 pm-10:25 pm
1 stop8h 25m
Minneapolis St Paul
Mon 8/31
7:00 am-10:49 am
Nonstop2h 49m
$349
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 6/18
6:00 am-9:59 am
1 stop4h 59m
Madison Truax Field
Tue 6/23
6:30 am-2:34 pm
2 stops7h 04m
$349
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-MSN
PWM-MSP
PWM-GRB
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-ORD
PWM-MSN
PWM-MSP
PWM-GRB
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in November is currently the most expensive (average of $248). 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?
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 April 1, 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
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
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 April 1, 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$429 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$476 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$431 | FlexibilityNo cancel fee | On-time63% |