$87+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 24 — May 311
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 24, 2026.
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 4/20![Sun Country Air logo]()
$177
This Trip.com deal was found by Cheapflights users on 4/19. 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 Trip.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
Sun 7/198:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/19![Sun Country Air logo]()
$205
This Trip.com deal was found by Cheapflights users on 4/19. 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 Trip.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
Mon 7/208:40 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/19![Sun Country Air logo]()
$227
This Delta deal was found by Cheapflights users on 4/20. 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 8/201:35 pm
PWM
- ORD
1 stop7h 42m
Delta
Sun 8/237:00 am
ORD
- PWM
1 stop5h 21m
Delta
Deal found 4/20![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 5/196:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Thu 5/214:00 pm
ORD
- PWM
1 stop6h 51m
United Airlines
Deal found 4/20![United Airlines logo]()
$263
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:45 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sat 7/48:20 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/20![Sun Country Air logo]()
$267
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/133:39 pm
PWM
- ORD
1 stop7h 01m
United Airlines
Fri 5/155:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 4/21![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 4/20. 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 5/224:56 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Mon 5/256:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/20![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/136:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Fri 5/157:44 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/20![American Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 5/246:00 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Wed 5/278:11 am
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 4/21![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 9/17:35 pm
PWM
- ORD
1 stop4h 46m
United Airlines
Wed 9/26:18 pm
ORD
- PWM
1 stop4h 41m
United Airlines
Deal found 4/20![United Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 4/21. 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 5/112:38 pm
PWM
- ORD
1 stop7h 58m
Delta
Sun 5/175:30 am
ORD
- PWM
1 stop6h 40m
Delta
Deal found 4/21![Delta logo]()
$274
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 24, 2026.
Discover carefully curated flight deals from Portland to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:50 pm
PWM
- ORD
Nonstop2h 58m
United Airlines
Sun 5/177:00 am
ORD
- PWM
Nonstop2h 28m
United Airlines
Deal found 4/22![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/21. 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 5/112:38 pm
PWM
- ORD
1 stop7h 58m
Delta
Sun 5/175:30 am
ORD
- PWM
1 stop6h 40m
Delta
Deal found 4/21![Delta logo]()
$274
This American Airlines deal was found by Cheapflights users on 4/19. 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 5/222:24 pm
PWM
- GRB
2 stops10h 29m
American Airlines
Sun 5/246:00 am
GRB
- PWM
2 stops10h 07m
American Airlines
Deal found 4/19![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:55 pm
PWM
- MSP
1 stop7h 10m
Southwest
Mon 6/156:00 pm
MSP
- PWM
1 stop5h 05m
Southwest
Deal found 4/23![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 4/21. 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 6/1212:40 pm
PWM
- ORD
1 stop6h 49m
Delta
Mon 6/158:52 am
ORD
- PWM
1 stop6h 08m
Delta
Deal found 4/21![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 4/20. 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 5/216:25 pm
PWM
- GRB
1 stop5h 15m
United Airlines
Tue 5/266:30 am
GRB
- PWM
1 stop6h 56m
United Airlines
Deal found 4/20![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
PWM
- ORD
2 stops9h 14m
Delta
Wed 7/810:30 am
ORD
- PWM
1 stop5h 20m
Delta
Deal found 4/23![Delta logo]()
$294
This American Airlines deal was found by Cheapflights users on 4/22. 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.
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 4/22![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/19. 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 5/224:56 pm
PWM
- GRB
1 stop6h 44m
United Airlines
Sun 5/243:46 pm
GRB
- PWM
1 stop5h 05m
United Airlines
Deal found 4/19![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Fri 5/297:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Wed 6/36:30 pm
CWA
- PWM
1 stop5h 05m
American Airlines
Deal found 4/22![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 4/19. 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.
Mon 6/156:57 pm
PWM
- ORD
1 stop6h 02m
Delta
Thu 6/188:52 am
ORD
- PWM
1 stop6h 08m
Delta
Deal found 4/19![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
PWM
- ORD
1 stop6h 03m
United Airlines
Thu 8/136:35 am
ORD
- PWM
Nonstop2h 37m
United Airlines
Deal found 4/23![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:30 am
PWM
- MKE
1 stop4h 25m
Southwest
Tue 6/234:10 pm
MKE
- PWM
1 stop4h 20m
Southwest
Deal found 4/21![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
PWM
- MSN
1 stop4h 44m
United Airlines
Mon 8/248:10 am
MSN
- PWM
1 stop5h 18m
United Airlines
Deal found 4/22![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 4/20. 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 5/136:02 am
PWM
- ORD
2 stops7h 59m
Delta
Fri 5/152:45 pm
ORD
- PWM
1 stop7h 33m
Delta
Deal found 4/20![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:20 pm
PWM
- MSP
1 stop7h 30m
Southwest
Sat 6/2012:50 pm
MSP
- PWM
1 stop7h 10m
Southwest
Deal found 4/23![Southwest logo]()
$409
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/287:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Tue 6/29:51 am
CWA
- PWM
2 stops11h 50m
American Airlines
Deal found 4/22![American Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:25 am
PWM
- MSN
2 stops10h 59m
Delta
Mon 8/312:03 pm
MSN
- PWM
2 stops10h 11m
Delta
Deal found 4/22![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 4/19. 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 9/256:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Mon 9/286:00 pm
ORD
- PWM
Nonstop2h 27m
United Airlines
Deal found 4/19![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:05 pm
PWM
- MKE
2 stops8h 10m
Southwest
Sun 8/165:45 am
MKE
- PWM
2 stops9h 50m
Southwest
Deal found 4/22![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:50 pm
PWM
- ORD
2 stops12h 09m
Delta
Tue 5/197:00 am
ORD
- PWM
1 stop3h 55m
Delta
Deal found 4/22![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Mon 7/2010:55 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 4/23![United Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Thu 5/217:19 pm
PWM
- CWA
1 stop5h 36m
American Airlines
Tue 5/263:12 pm
CWA
- PWM
2 stops16h 41m
American Airlines
Deal found 4/21![American Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:57 pm
PWM
- MSP
1 stop6h 20m
Delta
Sat 6/2010:00 am
MSP
- PWM
Nonstop2h 41m
Delta
Deal found 4/23![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:30 am
PWM
- MSP
1 stop5h 35m
Southwest
Sat 8/112:50 pm
MSP
- PWM
1 stop7h 10m
Southwest
Deal found 4/22![Southwest logo]()
$469
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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
Tue 5/266:00 am
CWA
- PWM
1 stop4h 46m
American Airlines
Deal found 4/24![American Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
PWM
- MKE
1 stop6h 35m
United Airlines
Sun 8/162:40 pm
MKE
- PWM
1 stop6h 21m
United Airlines
Deal found 4/22![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:57 pm
PWM
- MSP
1 stop6h 20m
Delta
Sun 7/196:55 am
MSP
- PWM
Nonstop2h 47m
Delta
Deal found 4/22![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:24 pm
PWM
- GRB
2 stops10h 29m
American Airlines
Tue 5/2612:15 pm
GRB
- PWM
2 stops10h 36m
American Airlines
Deal found 4/20![American Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
PWM
- MKE
1 stop6h 19m
United Airlines
Wed 5/272:50 pm
MKE
- PWM
1 stop6h 01m
United Airlines
Deal found 4/22![United Airlines logo]()
$370
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated April 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:03 am
PWM
- ORD
1 stop6h 31m
Delta
Mon 5/1112:30 pm
ORD
- PWM
2 stops9h 39m
Delta
Deal found 4/23![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:50 pm
PWM
- ORD
2 stops8h 34m
Delta
Wed 5/132:00 pm
ORD
- PWM
2 stops9h 43m
Delta
Deal found 4/23![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 4/21. 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 5/112:38 pm
PWM
- ORD
1 stop7h 58m
Delta
Sun 5/175:30 am
ORD
- PWM
1 stop6h 40m
Delta
Deal found 4/21![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/133:39 pm
PWM
- ORD
1 stop7h 01m
United Airlines
Fri 5/155:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 4/21![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/136:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Fri 5/157:44 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/20![American Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:39 pm
PWM
- ORD
1 stop7h 01m
United Airlines
Sun 5/177:00 am
ORD
- PWM
Nonstop2h 28m
United Airlines
Deal found 4/23![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 5/166:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Tue 5/198:39 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 4/22![American Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 5/196:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Thu 5/214:00 pm
ORD
- PWM
1 stop6h 51m
United Airlines
Deal found 4/20![United Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 4/20. 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 5/224:56 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Mon 5/256:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 4/20![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:19 pm
PWM
- ORD
Nonstop3h 26m
American Airlines
Sun 5/247:58 am
ORD
- PWM
1 stop8h 09m
American Airlines
Deal found 4/20![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 5/246:00 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Wed 5/278:11 am
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 4/21![American Airlines logo]()
$271
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 4/20![Sun Country Air logo]()
$177
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 24, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Deal found 4/20![United Airlines logo]()
$87
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 5/195:15 pm
PWM
- ORD
1 stop6h 21m
Delta
Deal found 4/21![Delta logo]()
$99
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Mon 5/116:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Deal found 4/22![American Airlines logo]()
$105
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:35 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Deal found 4/20![Sun Country Air logo]()
$109
This Delta deal was found by Cheapflights users on 4/21. 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 5/112:38 pm
PWM
- ORD
1 stop7h 58m
Delta
Deal found 4/21![Delta logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Thu 7/1612:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/20![Sun Country Air logo]()
$118
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:50 pm
PWM
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/23![United Airlines logo]()
$125
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Tue 5/196:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Deal found 4/21![United Airlines logo]()
$127
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/222:35 pm
PWM
- MKE
1 stop6h 34m
Delta
Deal found 4/23![Delta logo]()
$132
This American Airlines deal was found by Cheapflights users on 4/20. 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 7/297:30 pm
PWM
- ORD
Nonstop3h 08m
American Airlines
Deal found 4/20![American Airlines logo]()
$135
This United Airlines deal was found by Cheapflights users on 4/21. 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 6/35:15 am
PWM
- MKE
2 stops8h 33m
United Airlines
Deal found 4/21![United Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 4/20![Sun Country Air logo]()
$138
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 24, 2026.
Round-trip from | $177 (Super.com) |
|---|---|
One-way from | $87 (American Airlines) |
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 24, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/15
4:50 pm-6:48 pm
Nonstop2h 58m
Chicago O'Hare Intl
Sun 5/17
7:00 am-10:28 am
Nonstop2h 28m
$269
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 5/11
2:38 pm-9:36 pm
1 stop7h 58m
Chicago O'Hare Intl
Sun 5/17
5:30 am-1:10 pm
1 stop6h 40m
$274
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 6/12
12:40 pm-6:29 pm
1 stop6h 49m
Chicago O'Hare Intl
Mon 6/15
8:52 am-4:00 pm
1 stop6h 08m
$289
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 7/4
6:00 am-2:14 pm
2 stops9h 14m
Chicago O'Hare Intl
Wed 7/8
10:30 am-4:50 pm
1 stop5h 20m
$294
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Thu 5/21
6:25 pm-10:40 pm
1 stop5h 15m
Green Bay Austin-Straubel
Tue 5/26
6:30 am-2:26 pm
1 stop6h 56m
$320
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 6/15
6:57 pm-11:59 pm
1 stop6h 02m
Chicago O'Hare Intl
Thu 6/18
8:52 am-4:00 pm
1 stop6h 08m
$328
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Fri 5/22
4:56 pm-10:40 pm
1 stop6h 44m
Green Bay Austin-Straubel
Sun 5/24
3:46 pm-9:51 pm
1 stop5h 05m
$329
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 8/11
6:00 am-11:03 am
1 stop6h 03m
Chicago O'Hare Intl
Thu 8/13
6:35 am-10:12 am
Nonstop2h 37m
$332
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 8/21
6:00 am-9:44 am
1 stop4h 44m
Madison Truax Field
Mon 8/24
8:10 am-2:28 pm
1 stop5h 18m
$333
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 5/13
6:02 am-1:01 pm
2 stops7h 59m
Chicago O'Hare Intl
Fri 5/15
2:45 pm-11:18 pm
1 stop7h 33m
$333
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-GRB
PWM-MSP
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-ORD
PWM-GRB
PWM-MSP
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 24, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
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 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Wisconsin flights
Consider these flights traveling from Portland to Wisconsin.
Top 4 airlines flying from Portland to Wisconsin
Discover the top 4 airlines that operate flights from Portland to Wisconsin. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$437 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$437 | FlexibilityNo cancel fee | On-time63% |