$108+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Mar 24 — Mar 311
1 adult, Economy
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Find cheap flights from Portland to Wisconsin with Cheapflights
1. Tell us where you want to go
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 February 22, 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 February 22, 2026.
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 4/76:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 2/20![American Airlines logo]()
$209
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:46 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 8/178:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 2/20![Sun Country Air logo]()
$218
This Priceline deal was found by Cheapflights users on 2/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:18 pm
PWM
- ORD
1 stop9h 39m
JetBlue
Mon 5/256:00 am
ORD
- PWM
1 stop6h 23m
JetBlue
Deal found 2/21![JetBlue logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 5/226:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Fri 6/53:53 pm
ORD
- PWM
1 stop6h 58m
United Airlines
Deal found 2/20![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 5/2212:52 pm
PWM
- ORD
1 stop6h 21m
Delta
Mon 5/257:00 am
ORD
- PWM
1 stop3h 57m
Delta
Deal found 2/20![Delta logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Wed 3/256:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Wed 3/258:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/21![American Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 5/2112:52 pm
PWM
- ORD
1 stop6h 21m
Delta
Sat 6/61:44 pm
ORD
- PWM
2 stops9h 50m
Delta
Deal found 2/20![Delta logo]()
$234
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Wed 7/86:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Sun 7/126:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/21![United Airlines logo]()
$237
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 8/2612:04 pm
PWM
- ORD
Nonstop3h 01m
American Airlines
Sat 8/295:15 pm
ORD
- PWM
1 stop5h 36m
American Airlines
Deal found 2/20![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/19. 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 6/126:19 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Mon 6/154:40 pm
ORD
- PWM
1 stop5h 50m
United Airlines
Deal found 2/19![United Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/196:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Thu 3/2611:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/19![United Airlines logo]()
$241
This United Airlines deal was found by Cheapflights users on 2/19. 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 6/256:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Sun 6/286:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/19![United Airlines logo]()
$242
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 February 22, 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 February 22, 2026.
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 4/76:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 2/19![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/19. 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 5/86:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Wed 5/135:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 2/19![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:05 pm
PWM
- ORD
1 stop8h 48m
Delta
Sun 5/247:00 am
ORD
- PWM
1 stop4h 00m
Delta
Deal found 2/21![Delta logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2112:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 6/278:20 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 2/19![Sun Country Air logo]()
$307
This Southwest deal was found by Cheapflights users on 2/18. 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.
Thu 5/74:50 pm
PWM
- MKE
1 stop7h 20m
Southwest
Mon 5/115:50 am
MKE
- PWM
2 stops7h 20m
Southwest
Deal found 2/18![Southwest logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Sun 6/2812:40 pm
PWM
- MSP
Nonstop3h 08m
Multiple Airlines
Sat 7/46:40 am
MSP
- PWM
1 stop10h 06m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 5/237:16 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Mon 5/256:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/21![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 2/18. 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 3/276:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Sun 3/298:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/18![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/289:30 am
ORD
- PWM
1 stop7h 31m
Delta
Deal found 2/18![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/34:48 pm
PWM
- ORD
1 stop4h 35m
Delta
Sun 4/57:00 am
ORD
- PWM
1 stop5h 50m
Delta
Deal found 2/18![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/19. 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 6/256:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Sun 6/286:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/19![United Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:43 pm
PWM
- ORD
2 stops8h 16m
Delta
Wed 5/69:35 am
ORD
- PWM
1 stop6h 10m
Delta
Deal found 2/21![Delta logo]()
$234
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 3/186:00 am
PWM
- MSP
1 stop7h 43m
American Airlines
Wed 3/255:47 am
MSP
- PWM
1 stop5h 27m
American Airlines
Deal found 2/18![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Wed 5/206:00 am
PWM
- DLH
1 stop5h 34m
United Airlines
Wed 5/2711:18 am
DLH
- PWM
2 stops11h 33m
United Airlines
Deal found 2/21![United Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 2/22. 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 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 2/22![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/18. 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.
Fri 5/82:50 pm
PWM
- MKE
2 stops9h 35m
Southwest
Mon 5/117:10 am
MKE
- PWM
1 stop6h 00m
Southwest
Deal found 2/18![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 3/105:23 am
PWM
- MSN
1 stop6h 08m
Delta
Mon 3/161:24 pm
MSN
- PWM
2 stops9h 35m
Delta
Deal found 2/19![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Thu 6/185:15 am
PWM
- MSP
1 stop6h 13m
United Airlines
Sun 6/211:13 pm
MSP
- PWM
1 stop7h 38m
United Airlines
Deal found 2/18![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Thu 5/286:00 am
PWM
- MSP
1 stop7h 17m
United Airlines
Mon 6/11:13 pm
MSP
- PWM
1 stop7h 38m
United Airlines
Deal found 2/18![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/125:23 am
PWM
- MSN
1 stop6h 08m
Delta
Tue 3/173:08 pm
MSN
- PWM
1 stop7h 04m
Delta
Deal found 2/19![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/115:40 pm
PWM
- MKE
1 stop15h 09m
American Airlines
Tue 3/248:49 am
MKE
- PWM
1 stop7h 18m
American Airlines
Deal found 2/19![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 2/20. 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 5/75:30 am
PWM
- ATW
2 stops9h 31m
United Airlines
Sun 5/105:00 am
ATW
- PWM
1 stop4h 53m
United Airlines
Deal found 2/20![United Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/196:00 am
PWM
- ATW
2 stops7h 49m
American Airlines
Thu 3/261:25 pm
ATW
- PWM
1 stop9h 09m
American Airlines
Deal found 2/19![American Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 5/226:00 am
PWM
- MSP
1 stop5h 36m
United Airlines
Tue 5/261:08 pm
MSP
- PWM
2 stops9h 43m
United Airlines
Deal found 2/21![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/125:23 am
PWM
- MKE
1 stop6h 40m
Delta
Fri 3/202:40 pm
MKE
- PWM
1 stop7h 32m
Delta
Deal found 2/19![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 7/288:01 am
PWM
- MKE
1 stop5h 01m
American Airlines
Mon 8/35:51 pm
MKE
- PWM
1 stop5h 00m
American Airlines
Deal found 2/19![American Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 5/226:00 am
PWM
- MSP
1 stop5h 36m
United Airlines
Sun 5/241:08 pm
MSP
- PWM
2 stops9h 43m
United Airlines
Deal found 2/21![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 3/145:23 am
PWM
- MSN
1 stop6h 08m
Delta
Wed 3/183:08 pm
MSN
- PWM
1 stop18h 56m
Delta
Deal found 2/19![Delta logo]()
$391
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 3/205:40 pm
PWM
- ATW
1 stop6h 39m
American Airlines
Mon 3/231:25 pm
ATW
- PWM
2 stops8h 25m
American Airlines
Deal found 2/21![American Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 6/124:51 pm
PWM
- CWA
1 stop5h 36m
United Airlines
Mon 6/152:35 pm
CWA
- PWM
1 stop6h 16m
United Airlines
Deal found 2/20![United Airlines logo]()
$339
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated February 22, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 3/75:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Wed 3/1111:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/20![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 3/145:23 am
PWM
- MSN
1 stop6h 08m
Delta
Tue 3/177:00 am
MSN
- PWM
1 stop4h 09m
Delta
Deal found 2/19![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/165:48 pm
PWM
- ORD
1 stop5h 24m
Delta
Tue 3/172:38 pm
ORD
- PWM
2 stops8h 21m
Delta
Deal found 2/21![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1911:45 am
PWM
- ORD
1 stop6h 01m
Delta
Tue 3/247:10 am
ORD
- PWM
1 stop3h 59m
Delta
Deal found 2/21![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/196:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Thu 3/2611:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/19![United Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Fri 3/205:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Wed 3/258:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/19![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 3/206:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Wed 3/2512:03 pm
ORD
- PWM
1 stop5h 22m
United Airlines
Deal found 2/21![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/216:49 pm
PWM
- ORD
1 stop4h 57m
American Airlines
Sat 3/288:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/20![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/256:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Sat 3/285:47 pm
ORD
- PWM
Nonstop2h 17m
United Airlines
Deal found 2/19![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Wed 3/256:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Wed 3/258:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/21![American Airlines logo]()
$231
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/266:00 am
PWM
- ORD
1 stop5h 51m
United Airlines
Sat 3/283:40 pm
ORD
- PWM
1 stop6h 12m
United Airlines
Deal found 2/20![United Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/315:40 pm
PWM
- MSP
1 stop7h 33m
American Airlines
Wed 4/15:35 pm
MSP
- PWM
1 stop5h 20m
American Airlines
Deal found 2/19![American Airlines logo]()
$259
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 February 22, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/19![Sun Country Air logo]()
$108
This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline 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
Deal found 2/20![Sun Country Air logo]()
$114
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 3/1812:51 pm
PWM
- ORD
1 stop6h 43m
Delta
Deal found 2/20![Delta logo]()
$115
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/185:58 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/19![American Airlines logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares 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 2/21![Sun Country Air logo]()
$119
This Delta deal was found by Cheapflights users on 2/20. 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 4/214:43 pm
PWM
- ORD
1 stop4h 57m
Delta
Deal found 2/20![Delta logo]()
$126
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Tue 3/176:29 pm
PWM
- MSP
1 stop5h 55m
American Airlines
Deal found 2/21![American Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 2/19. 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 5/206:00 am
PWM
- ORD
2 stops11h 25m
Delta
Deal found 2/19![Delta logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/18. 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 5/65:30 am
PWM
- MSP
2 stops9h 48m
United Airlines
Deal found 2/18![United Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 6/116:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Deal found 2/20![Delta logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:36 pm
PWM
- MSP
Nonstop3h 06m
Sun Country Air
Deal found 2/20![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:56 pm
PWM
- ORD
2 stops23h 58m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$139
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 February 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (United Airlines) |
One-way from | $108 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $354 |
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 February 22, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Portland
Fly to
Wisconsin
Route
Depart
Return
Price
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/7
6:01 pm-8:14 pm
Nonstop3h 13m
Chicago O'Hare Intl
Sun 4/12
7:49 pm-11:27 pm
Nonstop2h 38m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/8
6:00 am-7:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 5/13
5:56 pm-9:19 pm
Nonstop2h 23m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/23
7:16 pm-11:26 pm
1 stop5h 10m
Chicago O'Hare Intl
Mon 5/25
6:18 pm-9:51 pm
Nonstop2h 33m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/22
2:05 pm-9:53 pm
1 stop8h 48m
Chicago O'Hare Intl
Sun 5/24
7:00 am-12:00 pm
1 stop4h 00m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 3/27
6:17 am-8:34 am
Nonstop3h 17m
Chicago O'Hare Intl
Sun 3/29
8:02 pm-11:34 pm
Nonstop2h 32m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 7/22
6:50 pm-11:55 pm
1 stop6h 05m
Chicago O'Hare Intl
Tue 7/28
9:30 am-6:01 pm
1 stop7h 31m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 4/3
4:48 pm-8:23 pm
1 stop4h 35m
Chicago O'Hare Intl
Sun 4/5
7:00 am-1:50 pm
1 stop5h 50m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/2
4:43 pm-11:59 pm
2 stops8h 16m
Chicago O'Hare Intl
Wed 5/6
9:35 am-4:45 pm
1 stop6h 10m
$234
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/25
6:25 pm-8:34 pm
Nonstop3h 09m
Chicago O'Hare Intl
Sun 6/28
6:25 pm-9:58 pm
Nonstop2h 33m
$242
PortlandDuluth
PWM - DLH
PWMDLH
Portland
Wed 5/20
6:00 am-10:34 am
1 stop5h 34m
Duluth Intl
Wed 5/27
11:18 am-11:51 pm
2 stops11h 33m
$274
Showing 1-10 of 60 results
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-MKE
PWM-MSN
PWM-DLH
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-MKE
PWM-MSN
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 February 22, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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
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 February 22, 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 February 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$244 | Average$475 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$413 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$431 | FlexibilityNo cancel fee | On-time63% |