$77+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 4 — Apr 111
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 March 5, 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 March 5, 2026.
This Booking.com deal was found by Cheapflights users on 3/4. 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 Booking.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 3/4![Sun Country Air logo]()
$198
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/76:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Mon 4/136:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/2![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/76:33 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Sat 4/111:00 pm
ORD
- PWM
1 stop5h 01m
United Airlines
Deal found 3/2![United Airlines logo]()
$219
This Priceline deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2412:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 7/278:00 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/2![Sun Country Air logo]()
$227
This American Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:39 pm
PWM
- ORD
1 stop5h 18m
American Airlines
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/1![American Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/169:40 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sat 5/165:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 3/1![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/2112:55 pm
PWM
- ORD
1 stop6h 10m
Delta
Sun 5/241:44 pm
ORD
- PWM
2 stops9h 59m
Delta
Deal found 3/1![Delta logo]()
$234
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/275:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Sun 3/296:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/3![United Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Thu 4/96:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Tue 4/144:30 pm
ORD
- PWM
1 stop5h 58m
United Airlines
Deal found 3/4![United Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:16 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Mon 5/256:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/28![United Airlines logo]()
$240
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/135:30 am
PWM
- ORD
2 stops8h 20m
Southwest
Mon 4/137:35 pm
ORD
- PWM
2 stops15h 45m
Southwest
Deal found 3/3![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/246:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Mon 4/277:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/2![American Airlines logo]()
$248
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 March 5, 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 March 5, 2026.
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Mon 5/46:17 pm
ORD
- PWM
1 stop4h 42m
United Airlines
Deal found 3/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:23 am
PWM
- ORD
2 stops12h 20m
Delta
Sun 4/57:00 am
ORD
- PWM
1 stop5h 50m
Delta
Deal found 3/1![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/25:40 am
PWM
- ORD
2 stops10h 50m
Southwest
Mon 5/42:40 pm
ORD
- PWM
2 stops7h 45m
Southwest
Deal found 3/1![Southwest logo]()
$306
This American Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:58 pm
PWM
- ATW
1 stop6h 21m
American Airlines
Wed 3/251:25 pm
ATW
- PWM
2 stops8h 25m
American Airlines
Deal found 3/1![American Airlines logo]()
$328
This Sun Country Air deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/2![Sun Country Air logo]()
$334
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/147:12 pm
PWM
- ORD
1 stop5h 25m
United Airlines
Tue 4/216:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/289:30 am
ORD
- PWM
1 stop7h 31m
Delta
Deal found 3/2![Delta logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Fri 5/156:00 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sun 5/175:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 3/4![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 3/4. 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 4/105:23 am
PWM
- ORD
2 stops12h 20m
Delta
Tue 4/148:52 am
ORD
- PWM
2 stops6h 53m
Delta
Deal found 3/4![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/26:33 pm
PWM
- MSP
1 stop6h 00m
United Airlines
Tue 4/710:00 am
MSP
- PWM
1 stop6h 32m
United Airlines
Deal found 3/2![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 2/28. 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.
Wed 4/86:03 am
PWM
- MSN
2 stops7h 38m
Delta
Tue 4/146:00 am
MSN
- PWM
2 stops8h 57m
Delta
Deal found 2/28![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 7/167:35 pm
PWM
- ATW
1 stop4h 56m
American Airlines
Mon 7/2010:54 am
ATW
- PWM
1 stop10h 47m
American Airlines
Deal found 3/2![American Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 3/4. 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.
Thu 8/65:55 am
PWM
- MSP
1 stop10h 05m
Southwest
Mon 8/105:45 am
MSP
- PWM
2 stops8h 15m
Southwest
Deal found 3/4![Southwest logo]()
$390
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/285:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Thu 5/284:00 pm
ORD
- PWM
1 stop6h 51m
United Airlines
Deal found 3/2![United Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/34:48 pm
PWM
- ORD
1 stop4h 35m
Delta
Mon 4/61:57 pm
ORD
- PWM
2 stops8h 15m
Delta
Deal found 3/3![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 8/226:50 pm
PWM
- MKE
1 stop5h 57m
American Airlines
Mon 8/246:00 am
MKE
- PWM
1 stop4h 34m
American Airlines
Deal found 3/3![American Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:45 am
PWM
- ATW
1 stop7h 13m
United Airlines
Wed 3/252:39 pm
ATW
- PWM
1 stop5h 32m
United Airlines
Deal found 3/1![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 3/4. 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 4/25:23 am
PWM
- MKE
1 stop6h 40m
Delta
Thu 4/97:00 am
MKE
- PWM
1 stop5h 50m
Delta
Deal found 3/4![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 3/4. 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 3/317:33 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Thu 4/26:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/4![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/1010:30 am
PWM
- MKE
2 stops7h 45m
Southwest
Sun 6/145:10 pm
MKE
- PWM
1 stop5h 55m
Southwest
Deal found 3/1![Southwest logo]()
$468
This American Airlines deal was found by Cheapflights users on 3/4. 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 6/181:35 pm
PWM
- MSN
1 stop7h 17m
American Airlines
Sun 6/215:52 pm
MSN
- PWM
1 stop4h 59m
American Airlines
Deal found 3/4![American Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:51 pm
PWM
- MSP
1 stop5h 45m
United Airlines
Tue 6/91:08 pm
MSP
- PWM
1 stop7h 44m
United Airlines
Deal found 3/2![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 2/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:12 pm
PWM
- MSP
1 stop5h 47m
United Airlines
Mon 4/131:04 pm
MSP
- PWM
1 stop7h 36m
United Airlines
Deal found 2/28![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/102:35 pm
PWM
- MKE
1 stop6h 34m
Delta
Sun 6/144:20 pm
MKE
- PWM
1 stop6h 33m
Delta
Deal found 3/1![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/267:40 am
PWM
- MKE
1 stop4h 30m
Southwest
Sun 7/56:50 am
MKE
- PWM
1 stop9h 10m
Southwest
Deal found 3/1![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 8/226:00 am
PWM
- MKE
1 stop8h 43m
Delta
Mon 8/242:45 pm
MKE
- PWM
1 stop6h 48m
Delta
Deal found 3/1![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:50 pm
PWM
- ATW
1 stop7h 15m
United Airlines
Mon 5/112:43 pm
ATW
- PWM
1 stop5h 36m
United Airlines
Deal found 3/2![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/253:10 pm
PWM
- MKE
2 stops9h 55m
Southwest
Sun 6/285:10 pm
MKE
- PWM
1 stop5h 55m
Southwest
Deal found 3/1![Southwest logo]()
$548
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/64:50 pm
PWM
- ATW
1 stop7h 15m
United Airlines
Sat 5/96:15 am
ATW
- PWM
1 stop6h 59m
United Airlines
Deal found 3/2![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/28. 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.
Wed 6/173:00 pm
PWM
- MSP
1 stop8h 25m
Delta
Sun 6/287:00 am
MSP
- PWM
Nonstop2h 49m
Delta
Deal found 2/28![Delta logo]()
$399
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated March 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated March 5, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/275:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Sun 3/296:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/3![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/14:48 pm
PWM
- ORD
1 stop4h 29m
Delta
Sun 4/57:10 am
ORD
- PWM
1 stop3h 59m
Delta
Deal found 3/3![Delta logo]()
$249
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/112:44 pm
PWM
- ORD
1 stop5h 39m
American Airlines
Sun 4/58:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 3/2![American Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:23 am
PWM
- ORD
2 stops12h 20m
Delta
Sun 4/57:00 am
ORD
- PWM
1 stop5h 50m
Delta
Deal found 3/1![Delta logo]()
$234
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/76:33 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Sat 4/111:55 pm
ORD
- PWM
Nonstop2h 37m
United Airlines
Deal found 3/2![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:39 pm
PWM
- ORD
1 stop5h 18m
American Airlines
Sun 4/127:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/1![American Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/76:03 am
PWM
- ORD
2 stops8h 14m
Delta
Mon 4/1311:00 am
ORD
- PWM
1 stop3h 57m
Delta
Deal found 3/2![Delta logo]()
$254
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Thu 4/96:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Tue 4/144:30 pm
ORD
- PWM
1 stop5h 58m
United Airlines
Deal found 3/4![United Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/135:30 am
PWM
- ORD
2 stops8h 20m
Southwest
Mon 4/137:35 pm
ORD
- PWM
2 stops15h 45m
Southwest
Deal found 3/3![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/246:01 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Mon 4/277:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 3/2![American Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 2/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:07 am
PWM
- MSP
1 stop7h 59m
American Airlines
Sat 5/22:36 pm
MSP
- PWM
1 stop7h 51m
American Airlines
Deal found 2/28![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 2/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:01 pm
PWM
- GRB
1 stop6h 30m
American Airlines
Sat 5/25:24 pm
GRB
- PWM
1 stop5h 03m
American Airlines
Deal found 2/28![American Airlines logo]()
$264
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 March 5, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 5, 2026.
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Wed 5/276:00 am
PWM
- ORD
1 stop5h 17m
JetBlue
Deal found 3/1![JetBlue logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 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 2/28![Sun Country Air logo]()
$98
This JetBlue deal was found by Cheapflights users on 3/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
PWM
- ORD
1 stop5h 17m
JetBlue
Deal found 3/4![JetBlue logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 7/1312:46 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/3![Sun Country Air logo]()
$108
This Priceline deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:16 am
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/3![Sun Country Air logo]()
$114
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/285:21 am
PWM
- ORD
1 stop8h 53m
Delta
Deal found 3/1![Delta logo]()
$115
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 3/316:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Deal found 3/3![United Airlines logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 3/4. 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 Cheapflightsfares 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 3/4![Sun Country Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/5. 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
1 stop12h 37m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/272:51 pm
PWM
- ORD
2 stops10h 08m
Delta
Deal found 3/2![Delta logo]()
$120
This JetBlue deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Tue 9/12:25 pm
PWM
- ORD
1 stop7h 19m
JetBlue
Deal found 3/2![JetBlue logo]()
$123
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/112:51 pm
PWM
- ORD
1 stop6h 43m
Delta
Deal found 3/2![Delta logo]()
$125
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 March 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Booking.com) |
One-way from | $77 (JetBlue) |
Popular in | November |
Cheapest in | September |
Average price | $369 |
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 March 5, 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 5/1
9:00 am-10:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Mon 5/4
6:17 pm-11:59 pm
1 stop4h 42m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/14
7:12 pm-11:37 pm
1 stop5h 25m
Chicago O'Hare Intl
Tue 4/21
6:10 pm-9:40 pm
Nonstop2h 30m
$219
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/15
6:00 am-7:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Sun 5/17
5:56 pm-9:19 pm
Nonstop2h 23m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 4/3
5:23 am-4:43 pm
2 stops12h 20m
Chicago O'Hare Intl
Sun 4/5
7:00 am-1:50 pm
1 stop5h 50m
$234
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 7/22
6:50 pm-11:55 pm
1 stop6h 05m
Chicago O'Hare Intl
Tue 7/28
9:30 am-6:01 pm
1 stop7h 31m
$249
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 4/10
5:23 am-4:43 pm
2 stops12h 20m
Chicago O'Hare Intl
Tue 4/14
8:52 am-4:45 pm
2 stops6h 53m
$259
PortlandMinneapolis
PWM - MSP
PWMMSP
Portland
Thu 4/2
6:33 pm-11:33 pm
1 stop6h 00m
Minneapolis St Paul
Tue 4/7
10:00 am-5:32 pm
1 stop6h 32m
$289
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 4/8
6:03 am-12:41 pm
2 stops7h 38m
Madison Truax Field
Tue 4/14
6:00 am-3:57 pm
2 stops8h 57m
$289
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/2
5:40 am-3:30 pm
2 stops10h 50m
Chicago O'Hare Intl
Mon 5/4
2:40 pm-11:25 pm
2 stops7h 45m
$306
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 5/28
5:15 am-9:36 am
1 stop5h 21m
Chicago O'Hare Intl
Thu 5/28
4:00 pm-11:51 pm
1 stop6h 51m
$307
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-GRB
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-GRB
PWM-ATW
What is the cheapest month to book a flight from Portland, Maine to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in November is currently the most expensive (average of $248). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated March 5, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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
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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 March 5, 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 March 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$491 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$431 | FlexibilityNo cancel fee | On-time63% |