$112+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 23 — Apr 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Wisconsin with Cheapflights
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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 March 24, 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 March 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/188:35 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/23![Sun Country Air logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/188:35 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/23![Sun Country Air logo]()
$217
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/1612:55 pm
PWM
- ORD
1 stop4h 34m
Delta
Tue 5/192:00 pm
ORD
- PWM
2 stops9h 43m
Delta
Deal found 3/23![Delta logo]()
$218
This Priceline deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
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 3/22![Sun Country Air logo]()
$237
This Super.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 7/267:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 3/20![Sun Country Air logo]()
$247
This KAYAK deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Thu 6/112:25 pm
PWM
- ORD
1 stop7h 19m
JetBlue
Mon 6/156:00 am
ORD
- PWM
1 stop6h 29m
JetBlue
Deal found 3/20![JetBlue logo]()
$251
This KAYAK deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 7/222:25 pm
PWM
- ORD
1 stop7h 19m
JetBlue
Tue 7/285:57 pm
ORD
- PWM
1 stop5h 00m
JetBlue
Deal found 3/22![JetBlue logo]()
$259
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/126:00 am
PWM
- MKE
1 stop8h 46m
Delta
Tue 5/197:15 am
MKE
- PWM
1 stop5h 43m
Delta
Deal found 3/23![Delta logo]()
$263
This Sun Country Air deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 7/912:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 7/127:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 3/19![Sun Country Air logo]()
$264
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/166:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Tue 5/191:59 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 3/23![American Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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
- ORD
Nonstop3h 00m
United Airlines
Sun 5/2410:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 3/19![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/18![American Airlines logo]()
$270
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 March 24, 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 March 24, 2026.
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/126:00 am
PWM
- MKE
1 stop8h 46m
Delta
Tue 5/197:15 am
MKE
- PWM
1 stop5h 43m
Delta
Deal found 3/23![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/56:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sat 5/95:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 3/18![United Airlines logo]()
$269
This Sun Country Air deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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.
Fri 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/18![Sun Country Air logo]()
$274
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/253:40 pm
PWM
- GRB
2 stops8h 51m
American Airlines
Wed 4/295:24 pm
GRB
- PWM
1 stop5h 03m
American Airlines
Deal found 3/20![American Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/165:40 am
PWM
- MSP
2 stops9h 30m
Southwest
Tue 6/22:15 pm
MSP
- PWM
2 stops7h 20m
Southwest
Deal found 3/18![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 6/116:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 6/136:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/21![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/212:51 pm
PWM
- ORD
1 stop8h 06m
Delta
Tue 4/286:21 pm
ORD
- PWM
1 stop5h 25m
Delta
Deal found 3/22![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/146:00 am
PWM
- ORD
1 stop7h 06m
United Airlines
Mon 4/206:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/22![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/106:01 pm
PWM
- ATW
1 stop6h 39m
American Airlines
Tue 4/146:31 pm
ATW
- PWM
1 stop4h 42m
American Airlines
Deal found 3/18![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/56:00 am
PWM
- ORD
1 stop6h 05m
Delta
Tue 5/55:04 pm
ORD
- PWM
2 stops6h 42m
Delta
Deal found 3/23![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/56:19 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Mon 6/154:40 pm
ORD
- PWM
1 stop5h 50m
United Airlines
Deal found 3/18![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 7/203:18 pm
ATW
- PWM
1 stop7h 51m
American Airlines
Deal found 3/22![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/81:18 pm
PWM
- ORD
2 stops9h 35m
Delta
Sun 5/107:00 am
ORD
- PWM
1 stop4h 00m
Delta
Deal found 3/19![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/147:33 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Sun 4/196:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/22![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/238:01 am
PWM
- MSN
1 stop5h 02m
American Airlines
Mon 5/257:18 am
MSN
- PWM
1 stop4h 22m
American Airlines
Deal found 3/23![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 6/115:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Mon 6/156:12 pm
ORD
- PWM
1 stop4h 39m
United Airlines
Deal found 3/19![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/235:40 am
PWM
- MSP
2 stops15h 15m
Southwest
Sat 5/3012:50 pm
MSP
- PWM
2 stops9h 20m
Southwest
Deal found 3/21![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/235:17 pm
PWM
- CWA
2 stops7h 38m
American Airlines
Wed 5/276:00 am
CWA
- PWM
1 stop4h 46m
American Airlines
Deal found 3/19![American Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/297:33 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Sat 5/26:00 am
ORD
- PWM
1 stop6h 27m
United Airlines
Deal found 3/18![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/292:51 pm
PWM
- MSN
2 stops9h 00m
Delta
Fri 5/293:40 pm
MSN
- PWM
1 stop6h 38m
Delta
Deal found 3/19![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/279:51 am
CWA
- PWM
2 stops11h 56m
American Airlines
Deal found 3/20![American Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/96:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sun 4/126:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/20![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/293:45 pm
PWM
- MKE
2 stops8h 25m
Southwest
Sat 8/111:35 am
MKE
- PWM
2 stops8h 25m
Southwest
Deal found 3/20![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:00 pm
PWM
- MKE
2 stops9h 45m
Southwest
Fri 6/55:15 pm
MKE
- PWM
2 stops5h 50m
Southwest
Deal found 3/21![Southwest logo]()
$478
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 7/296:00 am
PWM
- MKE
1 stop6h 51m
Delta
Thu 7/3010:11 am
MKE
- PWM
1 stop6h 41m
Delta
Deal found 3/22![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/76:33 pm
PWM
- ATW
1 stop5h 30m
United Airlines
Sat 4/113:46 pm
ATW
- PWM
1 stop4h 54m
United Airlines
Deal found 3/22![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/223:55 pm
PWM
- MSP
2 stops7h 40m
Southwest
Wed 4/2910:50 am
MSP
- PWM
2 stops10h 45m
Southwest
Deal found 3/23![Southwest logo]()
$480
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/2212:55 pm
PWM
- MSN
2 stops9h 32m
Delta
Mon 5/257:00 am
MSN
- PWM
1 stop4h 00m
Delta
Deal found 3/23![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/226:33 pm
PWM
- ATW
1 stop5h 30m
United Airlines
Tue 4/2812:34 pm
ATW
- PWM
2 stops9h 54m
United Airlines
Deal found 3/18![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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
- GRB
2 stops12h 39m
American Airlines
Sat 5/165:24 pm
GRB
- PWM
1 stop4h 58m
American Airlines
Deal found 3/20![American Airlines logo]()
$430
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated March 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated March 24, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/76:33 pm
PWM
- ATW
1 stop5h 30m
United Airlines
Sat 4/113:46 pm
ATW
- PWM
1 stop4h 54m
United Airlines
Deal found 3/22![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/76:01 pm
PWM
- ATW
1 stop6h 39m
American Airlines
Sat 4/111:30 pm
ATW
- PWM
2 stops8h 57m
American Airlines
Deal found 3/22![American Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/18![American Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/106:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sun 4/126:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/22![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/116:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 4/125:00 am
ORD
- PWM
1 stop5h 15m
American Airlines
Deal found 3/21![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 3/23![American Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/206:33 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Tue 4/216:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/20![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/212:51 pm
PWM
- ORD
1 stop8h 06m
Delta
Tue 4/281:36 pm
ORD
- PWM
2 stops10h 10m
Delta
Deal found 3/22![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/256:01 pm
PWM
- GRB
1 stop6h 30m
American Airlines
Wed 4/295:24 pm
GRB
- PWM
1 stop5h 03m
American Airlines
Deal found 3/20![American Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/294:28 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Sat 5/26:55 am
ORD
- PWM
Nonstop2h 28m
United Airlines
Deal found 3/18![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/295:02 pm
PWM
- MSN
1 stop5h 50m
American Airlines
Fri 5/296:46 am
MSN
- PWM
1 stop9h 00m
American Airlines
Deal found 3/19![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/306:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/23![American Airlines logo]()
$269
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 March 24, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 24, 2026.
This Expedia deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Tue 6/92:25 pm
PWM
- ORD
1 stop9h 31m
JetBlue
Deal found 3/21![JetBlue logo]()
$112
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/97:30 am
PWM
- MSP
1 stop5h 15m
Southwest
Deal found 3/23![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:30 am
PWM
- ORD
2 stops11h 35m
Southwest
Deal found 3/23![Southwest logo]()
$120
This Priceline deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Mon 6/12:37 pm
PWM
- ORD
1 stop9h 19m
JetBlue
Deal found 3/23![JetBlue logo]()
$124
This KAYAK deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 6/172:25 pm
PWM
- ORD
1 stop7h 19m
JetBlue
Deal found 3/20![JetBlue logo]()
$133
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/16:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Deal found 3/20![American Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/226:33 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Deal found 3/20![United Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/23![Sun Country Air logo]()
$138
This Expedia deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Thu 6/42:37 pm
PWM
- ORD
1 stop9h 21m
JetBlue
Deal found 3/22![JetBlue logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/276:30 pm
PWM
- MSP
1 stop21h 11m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$143
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/212:51 pm
PWM
- ORD
1 stop8h 06m
Delta
Deal found 3/20![Delta logo]()
$145
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/217:12 pm
PWM
- MSP
1 stop5h 47m
United Airlines
Deal found 3/22![United 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 March 24, 2026.
Round-trip from | $197 (Kiwi.com) |
|---|---|
One-way from | $112 (Expedia) |
Popular in | September |
Cheapest in | November |
Average price | $524 |
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 March 24, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMilwaukee
PWM - MKE
PWMMKE
Portland
Tue 5/12
6:00 am-1:46 pm
1 stop8h 46m
Milwaukee-Mitchell
Tue 5/19
7:15 am-1:58 pm
1 stop5h 43m
$263
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 5/5
6:00 am-7:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Sat 5/9
5:56 pm-9:19 pm
Nonstop2h 23m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/11
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sat 6/13
6:18 pm-9:51 pm
Nonstop2h 33m
$269
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Fri 7/17
12:40 pm-2:48 pm
Nonstop3h 08m
Minneapolis St Paul
Mon 7/20
8:40 am-12:19 pm
Nonstop2h 39m
$274
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/14
6:00 am-12:06 pm
1 stop7h 06m
Chicago O'Hare Intl
Mon 4/20
6:10 pm-9:40 pm
Nonstop2h 30m
$279
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 6/5
6:19 pm-8:28 pm
Nonstop3h 09m
Chicago O'Hare Intl
Mon 6/15
4:40 pm-11:30 pm
1 stop5h 50m
$279
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/14
7:33 pm-11:43 pm
1 stop5h 10m
Chicago O'Hare Intl
Sun 4/19
6:10 pm-9:40 pm
Nonstop2h 30m
$279
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/21
2:51 pm-9:57 pm
1 stop8h 06m
Chicago O'Hare Intl
Tue 4/28
6:21 pm-12:46 am
1 stop5h 25m
$289
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/11
5:15 am-9:36 am
1 stop5h 21m
Chicago O'Hare Intl
Mon 6/15
6:12 pm-11:51 pm
1 stop4h 39m
$289
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 4/29
7:33 pm-11:43 pm
1 stop5h 10m
Chicago O'Hare Intl
Sat 5/2
6:00 am-1:27 pm
1 stop6h 27m
$289
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-MSP
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-ORD
PWM-MSP
PWM-MSN
PWM-ATW
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.
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 March 24, 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.
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
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
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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 March 24, 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 March 24, 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% |