$88+ Cheap flights from Portland, ME (PWM) to Wisconsin
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 17 — May 241
Round-trip
1 adult, Economy
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Cheapest flights from Portland to WisconsinExplore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Booking.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Sun 5/317:55 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/12![Sun Country Air logo]()
$188
This Super.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
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 4/12![Sun Country Air logo]()
$225
This Trip.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/48:20 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/15![Sun Country Air logo]()
$238
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Thu 10/112:16 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Thu 10/87:55 am
MSP
- PWM
Nonstop2h 44m
Sun Country Air
Deal found 4/14![Sun Country Air logo]()
$247
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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
- ORD
Nonstop3h 26m
American Airlines
Mon 5/258:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/14![American Airlines logo]()
$269
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 7/198:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/14![Sun Country Air logo]()
$277
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/198:39 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/14![American Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:57 pm
PWM
- ORD
1 stop7h 02m
American Airlines
Sun 5/248:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/14![American Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/165:01 pm
PWM
- ORD
1 stop22h 38m
Multiple Airlines
Tue 5/193:55 pm
ORD
- PWM
2 stops23h 21m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/165:01 pm
PWM
- ORD
1 stop22h 38m
Multiple Airlines
Sat 5/231:50 pm
ORD
- PWM
2 stops28h 26m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 7/227:30 pm
PWM
- ORD
Nonstop3h 08m
American Airlines
Tue 7/288:25 pm
ORD
- PWM
Nonstop2h 44m
American Airlines
Deal found 4/15![American Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/291:35 pm
PWM
- ORD
1 stop6h 55m
American Airlines
Sun 5/318:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/15![American Airlines logo]()
$288
Best flights from Portland to WisconsinDiscover carefully curated flight deals from Portland to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Portland to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/304:58 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 6/66:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/12![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/265:57 pm
PWM
- MSN
1 stop7h 12m
American Airlines
Tue 6/27:18 am
MSN
- PWM
1 stop4h 46m
American Airlines
Deal found 4/15![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/171:12 pm
PWM
- ORD
2 stops11h 47m
Delta
Tue 6/236:05 am
ORD
- PWM
1 stop7h 14m
Delta
Deal found 4/14![Delta logo]()
$294
This Sun Country Air deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sun 6/2812:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Thu 7/28:25 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/15![Sun Country Air logo]()
$414
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/227:10 pm
PWM
- MSP
1 stop5h 45m
Southwest
Thu 7/234:25 pm
MSP
- PWM
2 stops6h 40m
Southwest
Deal found 4/16![Southwest logo]()
$414
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/76:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Mon 5/115:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 4/13![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/162:38 pm
PWM
- ORD
1 stop8h 18m
Delta
Tue 5/192:00 pm
ORD
- PWM
2 stops9h 43m
Delta
Deal found 4/13![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Sun 5/315:15 am
PWM
- ORD
1 stop7h 38m
United Airlines
Sat 6/66:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/12![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:00 pm
PWM
- ORD
2 stops9h 57m
Delta
Sat 8/295:30 am
ORD
- PWM
1 stop5h 52m
Delta
Deal found 4/12![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/14![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/205:30 am
PWM
- ORD
1 stop5h 07m
United Airlines
Wed 5/278:40 am
ORD
- PWM
1 stop4h 54m
United Airlines
Deal found 4/12![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/226:30 am
PWM
- ORD
1 stop6h 47m
Delta
Tue 7/281:44 pm
ORD
- PWM
2 stops8h 46m
Delta
Deal found 4/16![Delta logo]()
$294
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/16:00 am
PWM
- MSN
1 stop4h 59m
United Airlines
Tue 7/76:30 am
MSN
- PWM
1 stop6h 56m
United Airlines
Deal found 4/14![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/264:48 pm
PWM
- ORD
1 stop4h 26m
Delta
Tue 6/25:30 am
ORD
- PWM
2 stops9h 37m
Delta
Deal found 4/16![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/36:10 am
PWM
- MKE
2 stops10h 15m
Southwest
Mon 6/85:15 pm
MKE
- PWM
2 stops5h 50m
Southwest
Deal found 4/14![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/19:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Tue 5/57:00 am
ORD
- PWM
1 stop5h 27m
United Airlines
Deal found 4/16![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/173:45 pm
PWM
- MSP
2 stops9h 10m
Southwest
Sun 6/2112:30 pm
MSP
- PWM
1 stop9h 40m
Southwest
Deal found 4/13![Southwest logo]()
$439
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/264:48 pm
PWM
- MSN
1 stop5h 01m
Delta
Tue 6/21:29 pm
MSN
- PWM
2 stops8h 49m
Delta
Deal found 4/15![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/96:00 am
PWM
- MSN
1 stop4h 59m
United Airlines
Wed 7/156:30 am
MSN
- PWM
1 stop6h 56m
United Airlines
Deal found 4/14![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 7/311:48 am
PWM
- MSP
Nonstop3h 02m
Delta
Wed 7/86:55 am
MSP
- PWM
Nonstop2h 47m
Delta
Deal found 4/13![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 7/166:00 am
PWM
- ATW
1 stop9h 48m
American Airlines
Mon 7/2010:54 am
ATW
- PWM
1 stop12h 15m
American Airlines
Deal found 4/12![American Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/74:50 pm
PWM
- ATW
1 stop5h 40m
United Airlines
Sun 5/102:43 pm
ATW
- PWM
1 stop5h 36m
United Airlines
Deal found 4/16![United Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Sun 9/66:00 am
PWM
- DLH
1 stop5h 30m
United Airlines
Sat 9/125:00 am
DLH
- PWM
2 stops8h 35m
United Airlines
Deal found 4/13![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:39 pm
PWM
- ATW
2 stops11h 26m
American Airlines
Wed 10/149:55 am
ATW
- PWM
2 stops9h 19m
American Airlines
Deal found 4/14![American Airlines logo]()
$538
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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
Thu 5/283:03 pm
DLH
- PWM
2 stops7h 48m
United Airlines
Deal found 4/15![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/182:38 pm
PWM
- MKE
1 stop8h 14m
Delta
Sun 5/249:35 am
MKE
- PWM
1 stop5h 32m
Delta
Deal found 4/12![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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
- MKE
1 stop4h 25m
Delta
Wed 5/67:10 am
MKE
- PWM
1 stop6h 01m
Delta
Deal found 4/12![Delta logo]()
$411
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/76:00 am
PWM
- GRB
2 stops8h 58m
United Airlines
Sun 5/106:30 am
GRB
- PWM
1 stop6h 44m
United Airlines
Deal found 4/16![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 stop5h 07m
Delta
Sun 9/206:00 am
MKE
- PWM
1 stop6h 21m
Delta
Deal found 4/16![Delta logo]()
$417
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 6/34:51 pm
PWM
- MKE
1 stop4h 55m
United Airlines
Mon 6/81:30 pm
MKE
- PWM
1 stop7h 21m
United Airlines
Deal found 4/15![United Airlines logo]()
$350
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/156:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sun 5/176:55 am
ORD
- PWM
Nonstop2h 28m
United Airlines
Deal found 4/12![United Airlines logo]()
$296
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/198:39 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/14![American Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/165:01 pm
PWM
- ORD
1 stop22h 38m
Multiple Airlines
Tue 5/193:55 pm
ORD
- PWM
2 stops23h 21m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/165:01 pm
PWM
- ORD
1 stop22h 38m
Multiple Airlines
Sat 5/231:50 pm
ORD
- PWM
2 stops28h 26m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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
Sat 5/238:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/16![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/194:50 pm
PWM
- ORD
Nonstop2h 58m
United Airlines
Sun 5/2410:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 4/16![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/192:38 pm
PWM
- ORD
1 stop7h 58m
Delta
Tue 5/2611:09 am
ORD
- PWM
2 stops11h 00m
Delta
Deal found 4/13![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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
- ORD
Nonstop3h 26m
American Airlines
Mon 5/258:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/14![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:57 pm
PWM
- ORD
1 stop7h 02m
American Airlines
Sun 5/248:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/14![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/265:57 pm
PWM
- MSN
1 stop7h 12m
American Airlines
Tue 6/27:18 am
MSN
- PWM
1 stop4h 46m
American Airlines
Deal found 4/15![American Airlines logo]()
$291
This Booking.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Sun 5/317:55 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/12![Sun Country Air logo]()
$188
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/291:35 pm
PWM
- ORD
1 stop6h 55m
American Airlines
Sun 5/318:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/15![American Airlines logo]()
$288
One-way flights from Portland to WisconsinSearch for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/1312:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/13![Sun Country Air logo]()
$88
This Super.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Thu 9/1012:18 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 4/15![Sun Country Air logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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
Deal found 4/14![Sun Country Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/165:01 pm
PWM
- ORD
1 stop22h 38m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$128
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/296:00 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Deal found 4/14![American Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 8/184:44 pm
PWM
- ORD
2 stops28h 11m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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
Deal found 4/13![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/135:01 pm
PWM
- ORD
2 stops30h 13m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 4/2910:57 am
PWM
- ORD
1 stop23h 08m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:48 pm
PWM
- ORD
1 stop4h 26m
Delta
Deal found 4/13![Delta logo]()
$145
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/113:30 pm
PWM
- ORD
Nonstop2h 50m
American Airlines
Deal found 4/16![American Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/1210:47 am
PWM
- MSP
1 stop7h 23m
American Airlines
Deal found 4/13![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 April 17, 2026.
Round-trip from | $188 (Booking.com) |
|---|---|
One-way from | $88 (Kiwi.com) |
Popular in | September |
Cheapest in | November |
Average price | $557 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Wisconsin that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/30
4:58 pm-6:58 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sat 6/6
6:18 pm-9:51 pm
Nonstop2h 33m
$269
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 5/7
6:00 am-7:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Mon 5/11
5:56 pm-9:19 pm
Nonstop2h 23m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Sun 5/31
5:15 am-11:53 am
1 stop7h 38m
Chicago O'Hare Intl
Sat 6/6
6:18 pm-9:51 pm
Nonstop2h 33m
$279
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 5/20
5:30 am-9:37 am
1 stop5h 07m
Chicago O'Hare Intl
Wed 5/27
8:40 am-2:34 pm
1 stop4h 54m
$289
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 5/26
5:57 pm-12:09 am
1 stop7h 12m
Madison Truax Field
Tue 6/2
7:18 am-1:04 pm
1 stop4h 46m
$291
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 7/1
6:00 am-9:59 am
1 stop4h 59m
Madison Truax Field
Tue 7/7
6:30 am-2:26 pm
1 stop6h 56m
$291
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 6/17
1:12 pm-11:59 pm
2 stops11h 47m
Chicago O'Hare Intl
Tue 6/23
6:05 am-2:19 pm
1 stop7h 14m
$294
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/16
2:38 pm-9:56 pm
1 stop8h 18m
Chicago O'Hare Intl
Tue 5/19
2:00 pm-12:43 am
2 stops9h 43m
$294
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 8/26
3:00 pm-11:57 pm
2 stops9h 57m
Chicago O'Hare Intl
Sat 8/29
5:30 am-12:22 pm
1 stop5h 52m
$294
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 7/22
6:30 am-12:17 pm
1 stop6h 47m
Chicago O'Hare Intl
Tue 7/28
1:44 pm-11:30 pm
2 stops8h 46m
$294
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-CWA
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-CWA
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 April 17, 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
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
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
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Wisconsin by cabin class
Find flights from Portland to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Wisconsin flights
Browse other Portland and Wisconsin flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Wisconsin flights
Consider these flights traveling from Portland to Wisconsin.
Top 4 airlines flying from Portland to Wisconsin
Discover the top 4 airlines that operate flights from Portland to Wisconsin. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$417 | FlexibilityNo cancel fee | On-time63% |