$133+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Aug 27 — Sep 31
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Wisconsin with Cheapflights
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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 July 28, 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 July 28, 2026.
This Sun Country Air deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:25 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Mon 8/318:15 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 7/27![Sun Country Air logo]()
$238
This JetBlue deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm
PWM
- ORD
1 stop8h 18m
JetBlue
Sun 8/236:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Deal found 7/28![JetBlue logo]()
$287
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/256:30 am
PWM
- ORD
Nonstop3h 08m
American Airlines
Mon 9/287:59 pm
ORD
- PWM
Nonstop2h 48m
American Airlines
Deal found 7/27![American Airlines logo]()
$295
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:15 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Mon 8/108:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 7/24![Sun Country Air logo]()
$296
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/512:10 pm
PWM
- ORD
1 stop8h 03m
Delta
Thu 9/103:40 pm
ORD
- PWM
1 stop6h 49m
Delta
Deal found 7/28![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:01 am
PWM
- ORD
2 stops10h 29m
Delta
Mon 8/245:40 pm
ORD
- PWM
1 stop4h 50m
Delta
Deal found 7/24![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/38:03 am
PWM
- ORD
1 stop5h 51m
United Airlines
Mon 10/126:10 pm
ORD
- PWM
Nonstop2h 36m
United Airlines
Deal found 7/26![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/136:00 am
PWM
- MSN
1 stop6h 54m
American Airlines
Sat 10/175:26 pm
MSN
- PWM
1 stop5h 15m
American Airlines
Deal found 7/25![American Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/254:40 pm
PWM
- ORD
2 stops8h 19m
Delta
Thu 11/265:30 am
ORD
- PWM
1 stop6h 33m
Delta
Deal found 7/25![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/255:08 pm
PWM
- ORD
Nonstop2h 57m
United Airlines
Mon 9/284:00 pm
ORD
- PWM
1 stop6h 59m
United Airlines
Deal found 7/27![United Airlines logo]()
$305
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:55 pm
PWM
- MSP
Nonstop3h 09m
Sun Country Air
Sat 8/88:15 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 7/24![Sun Country Air logo]()
$306
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/56:02 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Mon 9/142:10 pm
ORD
- PWM
Nonstop2h 44m
United Airlines
Deal found 7/27![United Airlines logo]()
$315
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 July 28, 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 July 28, 2026.
This Sun Country Air deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:25 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Mon 8/318:15 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 7/27![Sun Country Air logo]()
$238
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:01 am
PWM
- ORD
2 stops10h 29m
Delta
Mon 8/245:40 pm
ORD
- PWM
1 stop4h 50m
Delta
Deal found 7/24![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 11/178:47 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Wed 11/1810:50 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 7/27![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/112:03 pm
PWM
- GRB
1 stop6h 53m
American Airlines
Sun 9/135:43 am
GRB
- PWM
1 stop6h 22m
American Airlines
Deal found 7/25![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/33:40 pm
PWM
- MKE
1 stop6h 05m
Southwest
Tue 9/810:30 am
MKE
- PWM
2 stops9h 45m
Southwest
Deal found 7/25![Southwest logo]()
$330
This JetBlue deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:45 pm
PWM
- ORD
1 stop8h 13m
JetBlue
Mon 8/246:00 am
ORD
- PWM
1 stop6h 45m
JetBlue
Deal found 7/25![JetBlue logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/86:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Wed 9/96:07 pm
ORD
- PWM
Nonstop2h 37m
United Airlines
Deal found 7/27![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/23. 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 9/1112:55 pm
PWM
- GRB
1 stop5h 25m
Delta
Sun 9/135:30 am
GRB
- PWM
1 stop6h 34m
Delta
Deal found 7/23![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/102:03 pm
PWM
- GRB
1 stop6h 53m
American Airlines
Sun 9/135:43 am
GRB
- PWM
1 stop6h 22m
American Airlines
Deal found 7/27![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 10/146:00 am
PWM
- DLH
1 stop5h 42m
United Airlines
Wed 10/283:06 pm
DLH
- PWM
1 stop5h 45m
United Airlines
Deal found 7/27![United Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/36:02 am
PWM
- MKE
1 stop7h 54m
American Airlines
Tue 9/86:00 pm
MKE
- PWM
1 stop4h 41m
American Airlines
Deal found 7/25![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/101:05 pm
PWM
- MSP
2 stops9h 20m
Southwest
Sat 9/123:05 pm
MSP
- PWM
1 stop5h 00m
Southwest
Deal found 7/27![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/306:03 am
PWM
- ORD
1 stop7h 43m
Delta
Sun 11/18:29 am
ORD
- PWM
1 stop6h 33m
Delta
Deal found 7/26![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:08 pm
PWM
- ORD
Nonstop2h 57m
United Airlines
Sun 10/186:10 pm
ORD
- PWM
Nonstop2h 36m
United Airlines
Deal found 7/24![United Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 10/195:09 pm
PWM
- CWA
2 stops8h 09m
American Airlines
Sat 10/2411:30 am
CWA
- PWM
1 stop4h 34m
American Airlines
Deal found 7/25![American Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:20 am
PWM
- MKE
1 stop6h 20m
Southwest
Tue 10/132:30 pm
MKE
- PWM
1 stop7h 05m
Southwest
Deal found 7/27![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/96:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Sat 9/123:55 pm
ORD
- PWM
1 stop6h 37m
United Airlines
Deal found 7/27![United Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/2311:50 am
PWM
- MSP
Nonstop3h 00m
Delta
Mon 9/287:00 am
MSP
- PWM
Nonstop2h 45m
Delta
Deal found 7/27![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 10/16:30 am
PWM
- MKE
1 stop5h 15m
Southwest
Thu 10/85:00 pm
MKE
- PWM
1 stop3h 50m
Southwest
Deal found 7/27![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Mon 8/244:00 pm
ORD
- PWM
1 stop6h 59m
United Airlines
Deal found 7/24![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:52 pm
PWM
- MKE
1 stop5h 31m
American Airlines
Sun 9/205:03 am
MKE
- PWM
1 stop7h 02m
American Airlines
Deal found 7/23![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:50 am
PWM
- ATW
1 stop4h 40m
Delta
Tue 8/1811:09 am
ATW
- PWM
2 stops11h 04m
Delta
Deal found 7/24![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/308:47 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 11/16:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/26![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/115:05 pm
PWM
- MKE
1 stop5h 49m
American Airlines
Sun 9/132:48 pm
MKE
- PWM
1 stop7h 59m
American Airlines
Deal found 7/25![American Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 7/23. 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 8/2211:50 am
PWM
- MSP
Nonstop3h 00m
Delta
Tue 8/256:10 pm
MSP
- PWM
1 stop5h 49m
Delta
Deal found 7/23![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/14:47 pm
PWM
- MKE
1 stop4h 31m
Delta
Thu 9/36:45 am
MKE
- PWM
1 stop6h 28m
Delta
Deal found 7/24![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Sat 9/56:02 am
PWM
- MSN
1 stop5h 02m
United Airlines
Wed 9/91:00 pm
MSN
- PWM
1 stop7h 44m
United Airlines
Deal found 7/23![United Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/116:30 am
PWM
- CWA
1 stop5h 30m
American Airlines
Sun 9/135:05 pm
CWA
- PWM
1 stop5h 42m
American Airlines
Deal found 7/27![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/2111:50 am
PWM
- MSP
Nonstop3h 00m
Delta
Tue 8/257:00 am
MSP
- PWM
Nonstop2h 45m
Delta
Deal found 7/25![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/216:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Mon 8/245:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/25![United Airlines logo]()
$375
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated July 28, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:55 pm
PWM
- MSP
Nonstop3h 09m
Sun Country Air
Sat 8/88:15 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 7/24![Sun Country Air logo]()
$306
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:15 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Mon 8/108:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 7/24![Sun Country Air logo]()
$296
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:50 am
PWM
- ORD
1 stop6h 09m
Delta
Sat 8/151:50 pm
ORD
- PWM
1 stop6h 41m
Delta
Deal found 7/24![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Sat 8/156:02 am
PWM
- ORD
1 stop7h 52m
American Airlines
Sat 9/57:13 pm
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 7/24![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/185:30 am
PWM
- ORD
1 stop6h 38m
American Airlines
Fri 8/217:13 pm
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 7/26![American Airlines logo]()
$305
This JetBlue deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm
PWM
- ORD
1 stop8h 18m
JetBlue
Sun 8/236:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Deal found 7/28![JetBlue logo]()
$287
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:01 am
PWM
- ORD
2 stops10h 29m
Delta
Mon 8/245:40 pm
ORD
- PWM
1 stop4h 50m
Delta
Deal found 7/24![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:46 pm
PWM
- MKE
1 stop5h 28m
American Airlines
Sat 8/226:20 am
MKE
- PWM
1 stop7h 01m
American Airlines
Deal found 7/23![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/209:08 am
PWM
- ORD
Nonstop2h 59m
American Airlines
Sun 8/238:05 am
ORD
- PWM
Nonstop2h 33m
American Airlines
Deal found 7/25![American Airlines logo]()
$323
This Super.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/2112:51 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Mon 8/248:05 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 7/27![Sun Country Air logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:08 am
PWM
- MSP
1 stop16h 16m
American Airlines
Wed 9/212:57 pm
MSP
- PWM
1 stop8h 51m
American Airlines
Deal found 7/23![American Airlines logo]()
$321
This Sun Country Air deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:25 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Mon 8/318:15 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 7/27![Sun Country Air logo]()
$238
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 July 28, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/256:30 am
PWM
- ORD
2 stops11h 21m
Delta
Deal found 7/27![Delta logo]()
$133
This Super.com deal was found by Cheapflights users on 7/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:03 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 7/24![Sun Country Air logo]()
$138
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:10 am
PWM
- ORD
2 stops11h 41m
Delta
Deal found 7/24![Delta logo]()
$138
This Sun Country Air deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/2412:18 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Deal found 7/27![Sun Country Air logo]()
$139
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:09 pm
PWM
- ORD
Nonstop3h 21m
American Airlines
Deal found 7/23![American Airlines logo]()
$140
This JetBlue deal was found by Cheapflights users on 7/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:45 pm
PWM
- ORD
1 stop8h 13m
JetBlue
Deal found 7/24![JetBlue logo]()
$144
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/296:46 am
PWM
- ORD
Nonstop3h 14m
American Airlines
Deal found 7/26![American Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/27![United Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 7/23. 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 9/225:29 pm
PWM
- MKE
1 stop4h 51m
Delta
Deal found 7/23![Delta logo]()
$159
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Sun 9/66:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/23![United Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/276:30 am
PWM
- ORD
2 stops11h 21m
Delta
Deal found 7/27![Delta logo]()
$165
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Tue 10/67:00 am
PWM
- MSP
1 stop8h 52m
American Airlines
Deal found 7/24![American Airlines logo]()
$166
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 July 28, 2026.
Round-trip from | $238 (Sun Country Air) |
|---|---|
One-way from | $133 (Delta) |
Popular in | August |
Cheapest in | November |
Average price | $477 |
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 July 28, 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
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Fri 8/28
12:25 pm-2:28 pm
Nonstop3h 03m
Minneapolis St Paul
Mon 8/31
8:15 am-11:56 am
Nonstop2h 41m
$238
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 8/20
11:01 am-8:30 pm
2 stops10h 29m
Chicago O'Hare Intl
Mon 8/24
5:40 pm-11:30 pm
1 stop4h 50m
$297
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 11/17
8:47 am-10:47 am
Nonstop3h 00m
Chicago O'Hare Intl
Wed 11/18
10:50 am-2:16 pm
Nonstop2h 26m
$315
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 9/8
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 9/9
6:07 pm-9:44 pm
Nonstop2h 37m
$315
PortlandDuluth
PWM - DLH
PWMDLH
Portland
Wed 10/14
6:00 am-10:42 am
1 stop5h 42m
Duluth Intl
Wed 10/28
3:06 pm-9:51 pm
1 stop5h 45m
$318
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Fri 9/11
2:03 pm-7:56 pm
1 stop6h 53m
Green Bay Austin-Straubel
Sun 9/13
5:43 am-1:05 pm
1 stop6h 22m
$319
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Fri 9/11
12:55 pm-5:20 pm
1 stop5h 25m
Green Bay Austin-Straubel
Sun 9/13
5:30 am-1:04 pm
1 stop6h 34m
$319
PortlandGreen Bay
PWM - GRB
PWMGRB
Portland
Thu 9/10
2:03 pm-7:56 pm
1 stop6h 53m
Green Bay Austin-Straubel
Sun 9/13
5:43 am-1:05 pm
1 stop6h 22m
$319
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 10/15
5:08 pm-7:05 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 10/18
6:10 pm-9:46 pm
Nonstop2h 36m
$323
PortlandMilwaukee
PWM - MKE
PWMMKE
Portland
Thu 9/3
6:02 am-12:56 pm
1 stop7h 54m
Milwaukee-Mitchell
Tue 9/8
6:00 pm-11:41 pm
1 stop4h 41m
$325
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-MKE
PWM-ATW
PWM-MSN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Wisconsin
PWM-USWI
PWM-ORD
PWM-MSP
PWM-MKE
PWM-ATW
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, November is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $328). Flying from Portland, Maine to Wisconsin in December is currently the most expensive (average of $583). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated July 28, 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.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 July 28, 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 July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$441 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$381 | Average$399 | FlexibilityNo cancel fee | On-time63% |