$108+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Portland to Wisconsin with Cheapflights
1. Tell us where you want to go
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 February 4, 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 February 4, 2026.
This Booking.com deal was found by Cheapflights users on 2/3. 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 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 2/3![Sun Country Air logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 6/297:40 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 2/1![Sun Country Air logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/205:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Sun 3/296:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 2/2![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/266:00 am
PWM
- ORD
1 stop6h 38m
United Airlines
Tue 3/35:45 pm
ORD
- PWM
Nonstop2h 24m
United Airlines
Deal found 2/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/2. 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 2/256:30 am
PWM
- ORD
1 stop7h 59m
Delta
Wed 2/256:25 pm
ORD
- PWM
1 stop4h 53m
Delta
Deal found 2/2![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 2/3. 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 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/281:15 pm
ORD
- PWM
2 stops9h 44m
Delta
Deal found 2/3![Delta logo]()
$234
This JetBlue deal was found by Cheapflights users on 2/2. 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.
Thu 9/172:17 pm
PWM
- ORD
1 stop7h 32m
JetBlue
Sun 9/206:45 am
ORD
- PWM
1 stop5h 37m
JetBlue
Deal found 2/2![JetBlue logo]()
$235
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Fri 5/85:10 pm
PWM
- ORD
1 stop6h 37m
American Airlines
Mon 5/117:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 2/4![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 9/37:22 pm
PWM
- ORD
1 stop4h 53m
United Airlines
Mon 9/71:55 pm
ORD
- PWM
Nonstop2h 17m
United Airlines
Deal found 2/3![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 2/2. 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 2/256:00 am
PWM
- ORD
2 stops8h 20m
Delta
Thu 2/266:30 am
ORD
- PWM
1 stop4h 30m
Delta
Deal found 2/2![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 2/1. 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 2/186:00 am
PWM
- ORD
1 stop5h 49m
United Airlines
Mon 2/233:51 pm
ORD
- PWM
1 stop6h 29m
United Airlines
Deal found 2/1![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 4/247:07 am
PWM
- ORD
Nonstop3h 10m
American Airlines
Mon 4/278:16 pm
ORD
- PWM
1 stop12h 38m
American Airlines
Deal found 2/3![American Airlines logo]()
$251
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 February 4, 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 February 4, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 3/205:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Mon 3/238:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/3![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/1. 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 5/14:45 pm
PWM
- ORD
Nonstop2h 58m
United Airlines
Mon 5/45:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 2/1![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/2. 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 2/246:18 am
PWM
- ORD
1 stop8h 11m
Delta
Thu 2/266:30 am
ORD
- PWM
1 stop4h 30m
Delta
Deal found 2/2![Delta logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 6/1812:34 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Sun 6/217:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 2/4![Sun Country Air logo]()
$257
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 6/1710:30 am
PWM
- MSP
1 stop5h 35m
Southwest
Wed 6/247:05 am
MSP
- PWM
1 stop7h 00m
Southwest
Deal found 2/3![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Fri 5/87:07 am
PWM
- ORD
Nonstop3h 10m
American Airlines
Mon 5/117:49 pm
ORD
- PWM
Nonstop2h 38m
American Airlines
Deal found 2/4![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/2. 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 7/285:20 am
PWM
- ORD
1 stop5h 16m
United Airlines
Sun 8/26:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/2![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/4. 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 5/812:52 pm
PWM
- ORD
1 stop4h 33m
Delta
Mon 5/117:00 am
ORD
- PWM
1 stop3h 57m
Delta
Deal found 2/4![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 6/47:15 pm
PWM
- ORD
1 stop5h 06m
United Airlines
Sun 6/76:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/2. 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.
Sat 5/161:40 pm
PWM
- ORD
1 stop6h 01m
Delta
Tue 5/196:00 am
ORD
- PWM
1 stop5h 44m
Delta
Deal found 2/2![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/266:00 am
PWM
- ORD
1 stop6h 38m
United Airlines
Tue 3/35:45 pm
ORD
- PWM
Nonstop2h 24m
United Airlines
Deal found 2/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/3. 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 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/289:30 am
ORD
- PWM
1 stop7h 31m
Delta
Deal found 2/3![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 5/169:40 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Tue 5/194:00 pm
ORD
- PWM
1 stop6h 59m
United Airlines
Deal found 2/2![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/45:40 pm
PWM
- GRB
1 stop6h 52m
American Airlines
Tue 3/109:51 am
GRB
- PWM
1 stop6h 16m
American Airlines
Deal found 2/2![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 2/284:15 pm
PWM
- ORD
Nonstop3h 12m
United Airlines
Wed 3/44:10 pm
ORD
- PWM
1 stop6h 10m
United Airlines
Deal found 2/2![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/266:00 am
PWM
- MSN
1 stop5h 01m
American Airlines
Wed 3/45:23 pm
MSN
- PWM
1 stop4h 36m
American Airlines
Deal found 2/2![American Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 3/612:13 pm
PWM
- ATW
1 stop6h 32m
Delta
Tue 3/1011:14 am
ATW
- PWM
1 stop3h 52m
Delta
Deal found 2/2![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 2/3. 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 4/272:50 pm
PWM
- MSP
2 stops10h 15m
Southwest
Wed 4/292:20 pm
MSP
- PWM
2 stops7h 00m
Southwest
Deal found 2/3![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 2/2. 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 3/42:35 pm
PWM
- ATW
2 stops8h 15m
Delta
Tue 3/1011:14 am
ATW
- PWM
1 stop3h 52m
Delta
Deal found 2/2![Delta logo]()
$262
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 4/107:07 am
PWM
- MSN
1 stop7h 41m
American Airlines
Mon 4/138:00 am
MSN
- PWM
1 stop6h 09m
American Airlines
Deal found 2/1![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 2/2. 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 3/42:35 pm
PWM
- GRB
2 stops8h 49m
Delta
Tue 3/1012:00 pm
GRB
- PWM
2 stops10h 22m
Delta
Deal found 2/2![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/244:15 pm
PWM
- MSP
1 stop6h 26m
United Airlines
Tue 3/311:04 pm
MSP
- PWM
1 stop7h 36m
United Airlines
Deal found 2/2![United Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 2/2. 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 5/145:51 pm
PWM
- GRB
1 stop6h 44m
American Airlines
Sat 5/165:24 pm
GRB
- PWM
1 stop5h 03m
American Airlines
Deal found 2/2![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/276:00 am
PWM
- MKE
1 stop6h 40m
American Airlines
Mon 3/29:00 am
MKE
- PWM
1 stop7h 07m
American Airlines
Deal found 2/2![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 3/612:13 pm
PWM
- GRB
1 stop5h 31m
Delta
Tue 3/107:00 am
GRB
- PWM
1 stop4h 09m
Delta
Deal found 2/2![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 2/286:00 am
PWM
- MSN
2 stops9h 07m
United Airlines
Mon 3/26:30 am
MSN
- PWM
2 stops6h 53m
United Airlines
Deal found 2/2![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 4/35:40 pm
PWM
- MKE
1 stop16h 20m
American Airlines
Mon 4/68:49 am
MKE
- PWM
1 stop7h 18m
American Airlines
Deal found 2/1![American Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 2/266:00 am
PWM
- MKE
2 stops7h 35m
United Airlines
Sun 3/16:00 am
MKE
- PWM
2 stops7h 23m
United Airlines
Deal found 2/3![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 2/1. 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 4/34:48 pm
PWM
- MSN
1 stop5h 18m
Delta
Sun 4/57:00 am
MSN
- PWM
1 stop4h 09m
Delta
Deal found 2/1![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 4/225:51 pm
PWM
- MKE
1 stop6h 49m
American Airlines
Sun 4/265:41 pm
MKE
- PWM
1 stop4h 46m
American Airlines
Deal found 2/3![American Airlines logo]()
$391
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated February 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/183:05 pm
PWM
- ORD
1 stop7h 29m
United Airlines
Mon 2/233:51 pm
ORD
- PWM
1 stop6h 29m
United Airlines
Deal found 2/2![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/195:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Wed 2/253:50 pm
ORD
- PWM
1 stop6h 30m
United Airlines
Deal found 2/1![United Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/195:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Tue 2/2411:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/1![United Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 2/1. 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 2/192:35 pm
PWM
- ORD
2 stops7h 09m
Delta
Wed 2/256:25 pm
ORD
- PWM
1 stop4h 53m
Delta
Deal found 2/1![Delta logo]()
$254
This Delta deal was found by Cheapflights users on 2/2. 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 2/246:00 am
PWM
- ORD
2 stops8h 20m
Delta
Thu 2/266:30 am
ORD
- PWM
1 stop4h 30m
Delta
Deal found 2/2![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 2/1. 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 2/252:35 pm
PWM
- ORD
1 stop8h 22m
Delta
Fri 2/276:25 pm
ORD
- PWM
1 stop4h 53m
Delta
Deal found 2/1![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 2/2. 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 2/256:00 am
PWM
- ORD
2 stops8h 20m
Delta
Thu 2/266:30 am
ORD
- PWM
1 stop4h 30m
Delta
Deal found 2/2![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/266:00 am
PWM
- ORD
1 stop6h 38m
United Airlines
Tue 3/35:45 pm
ORD
- PWM
Nonstop2h 24m
United Airlines
Deal found 2/1![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/2. 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 3/42:35 pm
PWM
- ATW
2 stops8h 15m
Delta
Tue 3/1011:14 am
ATW
- PWM
1 stop3h 52m
Delta
Deal found 2/2![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 3/612:13 pm
PWM
- ATW
1 stop6h 32m
Delta
Tue 3/1011:14 am
ATW
- PWM
1 stop3h 52m
Delta
Deal found 2/2![Delta logo]()
$257
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 3/65:07 pm
PWM
- ORD
1 stop5h 17m
American Airlines
Sun 3/88:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/1![American Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/205:45 am
PWM
- ORD
Nonstop3h 12m
United Airlines
Sun 3/296:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 2/2![United Airlines logo]()
$209
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 February 4, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:58 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/1![Sun Country Air logo]()
$108
This Delta deal was found by Cheapflights users on 2/2. 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.
Thu 3/192:30 pm
PWM
- ORD
1 stop8h 19m
Delta
Deal found 2/2![Delta logo]()
$115
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/35:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/3![American Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Fri 7/3112:45 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/3![Sun Country Air logo]()
$118
This Delta deal was found by Cheapflights users on 2/2. 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 3/315:23 am
PWM
- ORD
2 stops8h 54m
Delta
Deal found 2/2![Delta logo]()
$120
This Priceline deal was found by Cheapflights users on 2/3. 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.
Mon 8/312:34 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/3![Sun Country Air logo]()
$124
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 2/2812:45 pm
PWM
- ORD
1 stop4h 56m
Delta
Deal found 2/3![Delta logo]()
$126
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 2/245:07 pm
PWM
- MSP
1 stop5h 49m
American Airlines
Deal found 2/2![American Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 2/3. 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.
Tue 3/32:35 pm
PWM
- ORD
2 stops7h 09m
Delta
Deal found 2/3![Delta logo]()
$131
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
PWM
- ORD
1 stop8h 00m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$133
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/246:00 am
PWM
- MSP
2 stops9h 19m
United Airlines
Deal found 2/2![United Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 2/2. 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.
Thu 4/24:48 pm
PWM
- ORD
1 stop4h 29m
Delta
Deal found 2/2![Delta logo]()
$135
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Booking.com) |
One-way from | $108 (Kiwi.com) |
Popular in | September |
Cheapest in | November |
Average price | $329 |
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 February 4, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.
Fly from
Portland
Fly to
Wisconsin
Route
Depart
Return
Price
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 3/20
5:40 pm-7:50 pm
Nonstop3h 10m
Chicago O'Hare Intl
Mon 3/23
8:02 pm-11:34 pm
Nonstop2h 32m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/1
4:45 pm-6:43 pm
Nonstop2h 58m
Chicago O'Hare Intl
Mon 5/4
5:56 pm-9:19 pm
Nonstop2h 23m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/8
7:07 am-9:17 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 5/11
7:49 pm-11:27 pm
Nonstop2h 38m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 7/28
5:20 am-9:36 am
1 stop5h 16m
Chicago O'Hare Intl
Sun 8/2
6:25 pm-9:58 pm
Nonstop2h 33m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/4
7:15 pm-11:21 pm
1 stop5h 06m
Chicago O'Hare Intl
Sun 6/7
6:25 pm-9:58 pm
Nonstop2h 33m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 2/26
6:00 am-11:38 am
1 stop6h 38m
Chicago O'Hare Intl
Tue 3/3
5:45 pm-9:09 pm
Nonstop2h 24m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/16
9:40 am-11:36 am
Nonstop2h 56m
Chicago O'Hare Intl
Tue 5/19
4:00 pm-11:59 pm
1 stop6h 59m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 2/28
4:15 pm-6:27 pm
Nonstop3h 12m
Chicago O'Hare Intl
Wed 3/4
4:10 pm-11:20 pm
1 stop6h 10m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 2/24
6:18 am-1:29 pm
1 stop8h 11m
Chicago O'Hare Intl
Thu 2/26
6:30 am-12:00 pm
1 stop4h 30m
$229
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/8
12:52 pm-4:25 pm
1 stop4h 33m
Chicago O'Hare Intl
Mon 5/11
7:00 am-11:57 am
1 stop3h 57m
$229
Showing 1-10 of 60 results
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-MSN
PWM-ATW
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-MSN
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 February 4, 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
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 4, 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$244 | Average$489 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$419 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$383 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$311 | Average$396 | FlexibilityNo cancel fee | On-time63% |