$98+ 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
Jun 7 — Jun 141
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 May 8, 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 May 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 Cheapflightsfares 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
Sun 9/2712:15 pm
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 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
Sun 10/412:50 pm
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:54 pm
PWM
- MSP
Nonstop3h 06m
Sun Country Air
Mon 8/317:55 am
MSP
- PWM
Nonstop2h 46m
Sun Country Air
Deal found 5/6![Sun Country Air logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 10/812:35 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Sun 10/117:45 am
MSP
- PWM
Nonstop2h 44m
Sun Country Air
Deal found 5/3![Sun Country Air logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:29 pm
PWM
- MSP
Nonstop3h 06m
Sun Country Air
Mon 8/317:55 am
MSP
- PWM
Nonstop2h 46m
Sun Country Air
Deal found 5/6![Sun Country Air logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:36 pm
PWM
- MSP
Nonstop3h 06m
Sun Country Air
Sun 8/238:00 am
MSP
- PWM
Nonstop2h 44m
Sun Country Air
Deal found 5/6![Sun Country Air logo]()
$287
This Sun Country Air deal was found by Cheapflights users on 5/4. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:42 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 6/147:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/4![Sun Country Air logo]()
$288
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:36 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Tue 6/166:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/7![American Airlines logo]()
$291
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:05 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Mon 6/297:40 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$297
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:24 pm
PWM
- ORD
Nonstop3h 06m
American Airlines
Tue 7/79:03 pm
ORD
- PWM
Nonstop2h 34m
American Airlines
Deal found 5/6![American Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:30 pm
PWM
- MSP
Nonstop3h 06m
Sun Country Air
Mon 8/317:55 am
MSP
- PWM
Nonstop2h 46m
Sun Country Air
Deal found 5/6![Sun Country Air logo]()
$298
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 6/166:09 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Sat 6/209:10 pm
ORD
- PWM
Nonstop2h 43m
American Airlines
Deal found 5/4![American Airlines logo]()
$302
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 May 8, 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 May 8, 2026.
This Sun Country Air deal was found by Cheapflights users on 5/5. 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 6/1112:42 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 6/147:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$318
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:56 pm
PWM
- ATW
1 stop6h 56m
United Airlines
Tue 5/2610:38 am
ATW
- PWM
1 stop6h 06m
United Airlines
Deal found 5/7![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 5/266:00 am
PWM
- ORD
2 stops11h 51m
Delta
Thu 5/286:34 pm
ORD
- PWM
1 stop5h 09m
Delta
Deal found 5/5![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:24 pm
PWM
- ATW
2 stops10h 13m
American Airlines
Tue 5/265:35 am
ATW
- PWM
2 stops7h 53m
American Airlines
Deal found 5/7![American Airlines logo]()
$335
This JetBlue deal was found by Cheapflights users on 5/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:17 pm
PWM
- ORD
1 stop5h 03m
JetBlue
Wed 9/26:00 am
ORD
- PWM
1 stop6h 45m
JetBlue
Deal found 5/2![JetBlue logo]()
$378
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:20 pm
PWM
- MSP
1 stop7h 30m
Southwest
Mon 6/296:00 pm
MSP
- PWM
1 stop5h 05m
Southwest
Deal found 5/7![Southwest logo]()
$409
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 5/206:00 am
PWM
- ATW
1 stop4h 59m
United Airlines
Sun 5/248:00 am
ATW
- PWM
1 stop5h 26m
United Airlines
Deal found 5/5![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1611:02 am
PWM
- ORD
2 stops8h 27m
Delta
Tue 6/306:00 pm
ORD
- PWM
1 stop5h 52m
Delta
Deal found 5/7![Delta logo]()
$332
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Wed 5/276:30 pm
CWA
- PWM
1 stop5h 05m
American Airlines
Deal found 5/6![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 5/6. 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.
Wed 6/1011:48 am
PWM
- ORD
2 stops9h 43m
Delta
Sat 6/133:25 pm
ORD
- PWM
1 stop6h 40m
Delta
Deal found 5/6![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 5/196:00 am
PWM
- GRB
1 stop5h 00m
United Airlines
Sat 5/2312:34 pm
GRB
- PWM
2 stops10h 17m
United Airlines
Deal found 5/4![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 5/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:35 am
PWM
- MKE
1 stop7h 15m
Southwest
Thu 7/95:15 pm
MKE
- PWM
2 stops5h 50m
Southwest
Deal found 5/5![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 9/45:05 pm
PWM
- MSN
1 stop5h 00m
United Airlines
Sun 9/610:49 am
MSN
- PWM
2 stops7h 30m
United Airlines
Deal found 5/5![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 5/3. 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.
Tue 6/26:02 am
PWM
- MSP
1 stop8h 09m
Delta
Tue 6/97:00 am
MSP
- PWM
Nonstop2h 43m
Delta
Deal found 5/3![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:30 am
PWM
- MKE
2 stops7h 45m
Southwest
Sun 6/145:10 pm
MKE
- PWM
1 stop5h 55m
Southwest
Deal found 5/7![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 5/4. 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 6/186:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Tue 6/236:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 5/4![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 5/6. 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.
Wed 7/226:57 pm
PWM
- MSP
1 stop6h 20m
Delta
Sun 7/266:55 am
MSP
- PWM
Nonstop2h 47m
Delta
Deal found 5/6![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Thu 5/217:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Tue 5/263:12 pm
CWA
- PWM
2 stops16h 41m
American Airlines
Deal found 5/4![American Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 5/4. 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 6/121:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Fri 6/193:11 pm
MSN
- PWM
1 stop7h 18m
Delta
Deal found 5/4![Delta logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Tue 8/1110:55 am
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 5/6![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 5/4. 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 5/294:50 pm
PWM
- MKE
1 stop7h 20m
Southwest
Sun 5/314:45 pm
MKE
- PWM
2 stops6h 20m
Southwest
Deal found 5/4![Southwest logo]()
$438
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 5/2212:19 pm
PWM
- CWA
1 stop6h 41m
American Airlines
Tue 5/266:00 am
CWA
- PWM
2 stops10h 07m
American Airlines
Deal found 5/5![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 5/2. 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.
Wed 6/105:29 pm
PWM
- ORD
1 stop6h 05m
Delta
Sun 6/146:35 am
ORD
- PWM
1 stop5h 25m
Delta
Deal found 5/2![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
PWM
- ATW
1 stop6h 43m
United Airlines
Sat 7/183:44 pm
ATW
- PWM
2 stops7h 07m
United Airlines
Deal found 5/6![United Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:00 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 6/133:53 pm
ORD
- PWM
1 stop6h 58m
United Airlines
Deal found 5/6![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 5/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:30 am
PWM
- MKE
2 stops10h 25m
Southwest
Sun 9/205:45 am
MKE
- PWM
2 stops8h 55m
Southwest
Deal found 5/5![Southwest logo]()
$484
This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 9/156:00 am
PWM
- MKE
1 stop7h 32m
Delta
Sun 9/206:00 am
MKE
- PWM
1 stop6h 21m
Delta
Deal found 5/5![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/26:00 am
PWM
- MSP
1 stop5h 36m
United Airlines
Tue 6/91:08 pm
MSP
- PWM
2 stops9h 43m
United Airlines
Deal found 5/3![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 5/6. 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 7/42:51 pm
PWM
- MSN
1 stop7h 19m
Delta
Mon 7/66:00 am
MSN
- PWM
2 stops8h 55m
Delta
Deal found 5/6![Delta logo]()
$386
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
PWM
- MSN
1 stop4h 44m
United Airlines
Sat 9/53:49 pm
MSN
- PWM
1 stop5h 12m
United Airlines
Deal found 5/6![United Airlines logo]()
$371
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated May 8, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 5/3010:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 5/6![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/25:00 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Tue 6/911:00 am
ORD
- PWM
Nonstop2h 29m
United Airlines
Deal found 5/5![United Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:28 pm
PWM
- ATW
1 stop5h 41m
American Airlines
Sat 6/132:03 pm
ATW
- PWM
1 stop7h 40m
American Airlines
Deal found 5/6![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:36 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Tue 6/166:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/7![American Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:00 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 6/136:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 5/6![United Airlines logo]()
$307
This Sun Country Air deal was found by Cheapflights users on 5/4. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:42 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 6/147:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/4![Sun Country Air logo]()
$288
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 6/166:09 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Sat 6/209:10 pm
ORD
- PWM
Nonstop2h 43m
American Airlines
Deal found 5/4![American Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Wed 6/177:28 pm
PWM
- ORD
Nonstop3h 09m
American Airlines
Wed 6/248:59 pm
ORD
- PWM
Nonstop2h 43m
American Airlines
Deal found 5/2![American Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:58 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Tue 6/236:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/6![American Airlines logo]()
$315
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:05 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Mon 6/297:40 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$297
This Cheapflightsfares deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:05 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Sun 6/288:10 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/7![Sun Country Air logo]()
$317
This Delta deal was found by Cheapflights users on 5/4. 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.
Tue 6/3011:48 am
PWM
- ORD
1 stop6h 14m
Delta
Sun 7/56:05 am
ORD
- PWM
1 stop17h 47m
Delta
Deal found 5/4![Delta logo]()
$315
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 May 8, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:56 pm
PWM
- ORD
2 stops36h 59m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:44 pm
PWM
- ORD
2 stops28h 06m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 7/21:10 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Thu 5/287:56 pm
PWM
- ORD
2 stops24h 45m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/712:47 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 5/4![Sun Country Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Wed 5/2711:07 am
PWM
- ORD
1 stop13h 06m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:22 pm
PWM
- ORD
2 stops24h 28m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Sat 7/49:52 am
PWM
- ORD
1 stop14h 27m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Sun 5/247:56 pm
PWM
- ORD
2 stops36h 59m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Tue 5/266:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Wed 9/2312:25 pm
PWM
- ORD
Nonstop2h 55m
American Airlines
Deal found 5/4![American Airlines logo]()
$150
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 May 8, 2026.
Round-trip from | $227 (Cheapflightsfares) |
|---|---|
One-way from | $98 (Kiwi.com) |
Popular in | September |
Cheapest in | November |
Average price | $508 |
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 May 8, 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 6/11
12:42 pm-2:50 pm
Nonstop3h 08m
Minneapolis St Paul
Sun 6/14
7:55 am-11:37 am
Nonstop2h 42m
$318
PortlandAppleton
PWM - ATW
PWMATW
Portland
Fri 5/22
4:56 pm-10:52 pm
1 stop6h 56m
Appleton Intl
Tue 5/26
10:38 am-5:44 pm
1 stop6h 06m
$325
PortlandAppleton
PWM - ATW
PWMATW
Portland
Wed 5/20
6:00 am-9:59 am
1 stop4h 59m
Appleton Intl
Sun 5/24
8:00 am-2:26 pm
1 stop5h 26m
$325
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 5/26
6:00 am-4:51 pm
2 stops11h 51m
Chicago O'Hare Intl
Thu 5/28
6:34 pm-12:43 am
1 stop5h 09m
$327
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 6/16
11:02 am-6:29 pm
2 stops8h 27m
Chicago O'Hare Intl
Tue 6/30
6:00 pm-12:52 am
1 stop5h 52m
$332
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 6/10
11:48 am-8:31 pm
2 stops9h 43m
Chicago O'Hare Intl
Sat 6/13
3:25 pm-11:05 pm
1 stop6h 40m
$332
PortlandAppleton
PWM - ATW
PWMATW
Portland
Fri 5/22
2:24 pm-11:37 pm
2 stops10h 13m
Appleton Intl
Tue 5/26
5:35 am-2:28 pm
2 stops7h 53m
$335
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Tue 5/19
6:00 am-10:00 am
1 stop5h 00m
Green Bay Austin-Straubel
Sat 5/23
12:34 pm-11:51 pm
2 stops10h 17m
$344
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 9/4
5:05 pm-9:05 pm
1 stop5h 00m
Madison Truax Field
Sun 9/6
10:49 am-7:19 pm
2 stops7h 30m
$344
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/18
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Tue 6/23
6:18 pm-9:51 pm
Nonstop2h 33m
$347
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-MSN
PWM-ATW
PWM-MKE
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-MSN
PWM-ATW
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, December is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $193). Flying from Portland, Maine to Wisconsin in March is currently the most expensive (average of $329). 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 May 8, 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.
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
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 May 8, 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$438 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$422 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$477 | FlexibilityNo cancel fee | On-time63% |