$88+ Cheap flights from Portland, ME (PWM) to Wisconsin
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 9 — May 161
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Portland to WisconsinExplore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 9, 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 9, 2026.
This Super.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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
Sun 9/1311:10 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 4/8![Sun Country Air logo]()
$227
This Super.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/48:20 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/7![Sun Country Air logo]()
$267
This Sun Country Air deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:35 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Thu 10/157:55 am
MSP
- PWM
Nonstop2h 44m
Sun Country Air
Deal found 4/7![Sun Country Air logo]()
$268
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 5/246:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/5![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/5![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/5![American Airlines logo]()
$271
This Cheapflightsfares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 4/7![Sun Country Air logo]()
$277
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:15 am
PWM
- ORD
Nonstop3h 01m
American Airlines
Wed 8/267:10 pm
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 4/7![American Airlines logo]()
$278
This Super.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.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
Sat 6/208:20 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/7![Sun Country Air logo]()
$286
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:35 pm
PWM
- ORD
1 stop5h 26m
American Airlines
Sun 6/288:54 pm
ORD
- PWM
Nonstop2h 41m
American Airlines
Deal found 4/6![American Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:54 pm
PWM
- ORD
1 stop6h 44m
American Airlines
Mon 5/255:10 am
ORD
- PWM
1 stop7h 28m
American Airlines
Deal found 4/6![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
PWM
- MSN
1 stop7h 33m
American Airlines
Sat 5/168:05 am
MSN
- PWM
1 stop6h 02m
American Airlines
Deal found 4/6![American Airlines logo]()
$291
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 9, 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 9, 2026.
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/309:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sat 5/23:47 pm
ORD
- PWM
1 stop6h 42m
United Airlines
Deal found 4/9![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:02 am
PWM
- ORD
1 stop8h 19m
Delta
Sat 5/96:31 pm
ORD
- PWM
1 stop5h 12m
Delta
Deal found 4/6![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:45 pm
PWM
- MSP
1 stop5h 30m
Southwest
Sat 5/92:45 pm
MSP
- PWM
2 stops7h 25m
Southwest
Deal found 4/4![Southwest logo]()
$304
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:01 am
PWM
- MSN
1 stop7h 05m
American Airlines
Sat 8/85:44 pm
MSN
- PWM
1 stop5h 07m
American Airlines
Deal found 4/5![American Airlines logo]()
$373
This Sun Country Air deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air 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 4/7![Sun Country Air logo]()
$434
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Tue 5/1210:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 4/6![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:18 pm
PWM
- ORD
2 stops9h 35m
Delta
Tue 6/211:09 am
ORD
- PWM
2 stops11h 00m
Delta
Deal found 4/6![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:50 pm
PWM
- MSP
1 stop6h 06m
United Airlines
Sat 5/96:00 am
MSP
- PWM
1 stop7h 14m
United Airlines
Deal found 4/4![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 8/206:00 am
PWM
- ORD
1 stop5h 12m
Delta
Sun 8/237:00 am
ORD
- PWM
1 stop5h 21m
Delta
Deal found 4/8![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:35 pm
PWM
- ORD
1 stop7h 30m
United Airlines
Sun 9/206:35 am
ORD
- PWM
Nonstop2h 37m
United Airlines
Deal found 4/8![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:35 am
PWM
- ORD
2 stops9h 41m
Delta
Sat 5/96:31 pm
ORD
- PWM
1 stop5h 12m
Delta
Deal found 4/7![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:50 pm
PWM
- ORD
1 stop4h 41m
Delta
Mon 6/155:30 am
ORD
- PWM
2 stops10h 19m
Delta
Deal found 4/4![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Wed 5/276:30 pm
CWA
- PWM
1 stop5h 05m
American Airlines
Deal found 4/5![American Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:05 pm
PWM
- MSP
2 stops10h 40m
Southwest
Wed 7/14:55 pm
MSP
- PWM
1 stop5h 00m
Southwest
Deal found 4/6![Southwest logo]()
$433
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:30 am
PWM
- DLH
2 stops13h 05m
United Airlines
Sun 5/243:03 pm
DLH
- PWM
1 stop5h 48m
United Airlines
Deal found 4/4![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:03 am
PWM
- ORD
2 stops10h 11m
Delta
Sat 5/307:00 am
ORD
- PWM
1 stop3h 55m
Delta
Deal found 4/4![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 10/312:25 pm
PWM
- ATW
1 stop6h 13m
American Airlines
Wed 10/144:18 pm
ATW
- PWM
1 stop5h 27m
American Airlines
Deal found 4/8![American Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:30 am
PWM
- MSP
1 stop5h 35m
Southwest
Thu 6/184:25 pm
MSP
- PWM
2 stops6h 40m
Southwest
Deal found 4/4![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/1612:50 pm
PWM
- ORD
2 stops8h 34m
Delta
Tue 5/192:00 pm
ORD
- PWM
2 stops9h 43m
Delta
Deal found 4/9![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
PWM
- MSN
1 stop4h 59m
United Airlines
Sat 5/302:35 pm
MSN
- PWM
1 stop6h 16m
United Airlines
Deal found 4/8![United Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:20 pm
PWM
- MSP
2 stops8h 30m
Southwest
Sun 6/76:55 am
MSP
- PWM
1 stop9h 05m
Southwest
Deal found 4/5![Southwest logo]()
$450
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
Sun 4/266:00 am
PWM
- ORD
1 stop6h 05m
Delta
Wed 4/296:21 pm
ORD
- PWM
1 stop5h 25m
Delta
Deal found 4/9![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:50 pm
PWM
- MKE
1 stop4h 58m
United Airlines
Mon 5/45:55 am
MKE
- PWM
2 stops7h 54m
United Airlines
Deal found 4/6![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:25 pm
PWM
- ATW
2 stops11h 06m
American Airlines
Mon 7/203:18 pm
ATW
- PWM
1 stop7h 51m
American Airlines
Deal found 4/4![American Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:50 pm
PWM
- ORD
1 stop4h 39m
Delta
Sat 5/235:45 pm
ORD
- PWM
1 stop15h 32m
Delta
Deal found 4/4![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/294:51 pm
PWM
- DLH
1 stop7h 17m
United Airlines
Mon 6/13:03 pm
DLH
- PWM
1 stop5h 48m
United Airlines
Deal found 4/8![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/211:48 am
PWM
- MSP
Nonstop3h 02m
Delta
Tue 7/76:55 am
MSP
- PWM
Nonstop2h 47m
Delta
Deal found 4/4![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 am
PWM
- MSN
2 stops7h 07m
United Airlines
Sat 5/162:25 pm
MSN
- PWM
2 stops8h 34m
United Airlines
Deal found 4/6![United Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
PWM
- MKE
1 stop6h 10m
Delta
Mon 5/47:10 am
MKE
- PWM
1 stop6h 01m
Delta
Deal found 4/6![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/234:58 pm
PWM
- GRB
1 stop5h 32m
United Airlines
Wed 5/278:00 am
GRB
- PWM
1 stop5h 26m
United Airlines
Deal found 4/8![United Airlines logo]()
$391
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated April 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2811:42 am
PWM
- ORD
2 stops9h 34m
Delta
Wed 4/296:21 pm
ORD
- PWM
1 stop5h 25m
Delta
Deal found 4/5![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2811:42 am
PWM
- ORD
2 stops8h 10m
Delta
Tue 5/59:50 am
ORD
- PWM
2 stops12h 34m
Delta
Deal found 4/5![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:28 pm
PWM
- MSP
1 stop6h 32m
United Airlines
Tue 5/57:05 am
MSP
- PWM
1 stop5h 22m
United Airlines
Deal found 4/6![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/5![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 5/37:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/5![American Airlines logo]()
$271
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
PWM
- MSN
1 stop7h 33m
American Airlines
Sat 5/168:05 am
MSN
- PWM
1 stop6h 02m
American Airlines
Deal found 4/6![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 am
PWM
- ORD
2 stops11h 35m
Southwest
Mon 5/187:35 pm
ORD
- PWM
2 stops15h 45m
Southwest
Deal found 4/5![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 5/246:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/5![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:54 pm
PWM
- ORD
1 stop6h 44m
American Airlines
Mon 5/255:10 am
ORD
- PWM
1 stop7h 28m
American Airlines
Deal found 4/6![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
Sun 5/246:02 am
PWM
- ORD
1 stop8h 14m
Delta
Thu 5/287:00 am
ORD
- PWM
1 stop3h 55m
Delta
Deal found 4/8![Delta logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2711:07 am
PWM
- ORD
1 stop13h 06m
Multiple Airlines
Fri 5/291:50 pm
ORD
- PWM
2 stops25h 26m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:16 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Sun 5/316:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/6![United Airlines logo]()
$299
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 9, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Deal found 4/4![Sun Country Air logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:16 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 4/4![Sun Country Air logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com 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
Deal found 4/7![Sun Country Air logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/6![Sun Country Air logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/21:10 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Deal found 4/6![Sun Country Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/66:26 pm
PWM
- ORD
1 stop16h 01m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:34 am
PWM
- ORD
Nonstop3h 04m
United Airlines
Deal found 4/5![United Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:44 pm
PWM
- ORD
2 stops28h 11m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/6![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:29 am
PWM
- ORD
2 stops25h 54m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:44 pm
PWM
- ORD
2 stops28h 11m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:43 pm
PWM
- ORD
1 stop4h 57m
Delta
Deal found 4/5![Delta logo]()
$145
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 9, 2026.
Round-trip from | $227 (Super.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 9, 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
Thu 4/30
9:00 am-10:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Sat 5/2
3:47 pm-11:29 pm
1 stop6h 42m
$279
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/9
6:02 am-1:21 pm
1 stop8h 19m
Chicago O'Hare Intl
Sat 5/9
6:31 pm-12:43 am
1 stop5h 12m
$289
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Sun 5/10
6:00 am-7:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Tue 5/12
10:48 am-2:14 pm
Nonstop2h 26m
$289
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Sat 5/2
4:50 pm-9:56 pm
1 stop6h 06m
Minneapolis St Paul
Sat 5/9
6:00 am-2:14 pm
1 stop7h 14m
$299
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 9/18
2:35 pm-9:05 pm
1 stop7h 30m
Chicago O'Hare Intl
Sun 9/20
6:35 am-10:12 am
Nonstop2h 37m
$299
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/29
1:18 pm-9:53 pm
2 stops9h 35m
Chicago O'Hare Intl
Tue 6/2
11:09 am-11:09 pm
2 stops11h 00m
$300
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Sat 5/2
12:45 pm-5:15 pm
1 stop5h 30m
Minneapolis St Paul
Sat 5/9
2:45 pm-11:10 pm
2 stops7h 25m
$304
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 8/20
6:00 am-10:12 am
1 stop5h 12m
Chicago O'Hare Intl
Sun 8/23
7:00 am-1:21 pm
1 stop5h 21m
$309
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 5/6
11:35 am-8:16 pm
2 stops9h 41m
Chicago O'Hare Intl
Sat 5/9
6:31 pm-12:43 am
1 stop5h 12m
$314
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 6/12
4:50 pm-8:31 pm
1 stop4h 41m
Chicago O'Hare Intl
Mon 6/15
5:30 am-4:49 pm
2 stops10h 19m
$314
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-CWA
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-MSN
PWM-CWA
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 $97). Flying from Portland, Maine to Wisconsin in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Portland, Maine to Wisconsin?
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated April 9, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
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
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 9, 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 9, 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$417 | FlexibilityNo cancel fee | On-time63% |