$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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Mar 14 — Mar 211
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 12, 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 12, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:47 pm
PWM
- MSP
Nonstop3h 04m
Sun Country Air
Sun 5/317:54 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 6/114:58 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 6/146:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/10![United Airlines logo]()
$219
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 7/1712:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 2/10![Sun Country Air logo]()
$227
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:37 pm
PWM
- ORD
Nonstop3h 13m
American Airlines
Sun 11/81:42 pm
ORD
- PWM
Nonstop2h 25m
American Airlines
Deal found 2/9![American Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
PWM
- ORD
1 stop5h 57m
American Airlines
Sat 3/218:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/9![American Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/236:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Sun 4/266:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 2/10![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:50 pm
PWM
- ORD
1 stop6h 05m
Delta
Tue 7/281:15 pm
ORD
- PWM
2 stops9h 44m
Delta
Deal found 2/8![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:51 pm
PWM
- ORD
1 stop6h 43m
Delta
Mon 4/132:25 pm
ORD
- PWM
1 stop7h 58m
Delta
Deal found 2/9![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:20 am
PWM
- ORD
1 stop5h 16m
United Airlines
Sun 7/126:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$240
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/66:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Wed 3/1111:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/11![United Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/17:10 pm
PWM
- ORD
1 stop5h 34m
United Airlines
Sun 5/35:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 2/11![United Airlines logo]()
$245
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 12, 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 12, 2026.
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 6/114:58 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 6/146:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Fri 3/278:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/8![American Airlines logo]()
$209
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
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 2/12![Sun Country Air logo]()
$307
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:42 pm
PWM
- MSN
2 stops7h 09m
Delta
Tue 4/282:57 pm
MSN
- PWM
1 stop7h 27m
Delta
Deal found 2/8![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/81:00 pm
PWM
- MKE
2 stops9h 45m
Southwest
Wed 4/152:45 pm
MKE
- PWM
1 stop6h 35m
Southwest
Deal found 2/10![Southwest logo]()
$352
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 6/54:58 pm
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 6/76:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/11![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:34 am
PWM
- ORD
Nonstop3h 04m
United Airlines
Wed 5/65:56 pm
ORD
- PWM
Nonstop2h 23m
United Airlines
Deal found 2/9![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 6/46:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Sun 6/76:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 6/196:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 6/216:25 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 2/11![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:39 pm
PWM
- MSN
1 stop6h 46m
American Airlines
Tue 4/288:00 am
MSN
- PWM
1 stop6h 09m
American Airlines
Deal found 2/8![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/114:23 pm
PWM
- ORD
Nonstop3h 12m
United Airlines
Wed 3/1811:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/10![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
PWM
- MSN
1 stop6h 14m
American Airlines
Tue 4/285:42 pm
MSN
- PWM
1 stop5h 31m
American Airlines
Deal found 2/8![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:13 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Sat 4/41:00 pm
ORD
- PWM
1 stop5h 01m
United Airlines
Deal found 2/10![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/315:48 pm
PWM
- MKE
1 stop4h 57m
Delta
Sun 4/57:00 am
MKE
- PWM
1 stop5h 50m
Delta
Deal found 2/11![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:51 pm
PWM
- MSN
1 stop6h 44m
American Airlines
Sun 4/128:00 am
MSN
- PWM
1 stop7h 20m
American Airlines
Deal found 2/9![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:30 am
PWM
- MSP
2 stops10h 30m
Southwest
Wed 6/32:20 pm
MSP
- PWM
2 stops7h 00m
Southwest
Deal found 2/9![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 6/26:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 6/63:47 pm
ORD
- PWM
1 stop7h 03m
United Airlines
Deal found 2/11![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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
- MKE
1 stop4h 52m
Delta
Fri 4/33:55 pm
MKE
- PWM
1 stop6h 27m
Delta
Deal found 2/11![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/11![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 am
PWM
- MSP
2 stops11h 15m
Southwest
Sun 5/317:20 am
MSP
- PWM
1 stop8h 30m
Southwest
Deal found 2/9![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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
- MKE
1 stop4h 52m
Delta
Sun 4/59:32 am
MKE
- PWM
1 stop5h 34m
Delta
Deal found 2/11![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/236:00 pm
PWM
- MSN
1 stop6h 22m
American Airlines
Wed 3/254:20 pm
MSN
- PWM
1 stop6h 35m
American Airlines
Deal found 2/11![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/165:40 am
PWM
- MKE
1 stop7h 20m
Southwest
Tue 5/269:25 am
MKE
- PWM
2 stops11h 55m
Southwest
Deal found 2/10![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/315:48 pm
PWM
- MKE
1 stop4h 57m
Delta
Fri 4/36:45 am
MKE
- PWM
1 stop4h 24m
Delta
Deal found 2/11![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:52 pm
PWM
- MKE
1 stop4h 13m
Delta
Tue 5/265:30 am
MKE
- PWM
1 stop6h 14m
Delta
Deal found 2/10![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/66:00 am
PWM
- MSP
1 stop12h 15m
American Airlines
Mon 3/911:41 am
MSP
- PWM
1 stop11h 14m
American Airlines
Deal found 2/11![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:45 am
PWM
- GRB
1 stop5h 05m
United Airlines
Mon 3/23:05 pm
GRB
- PWM
1 stop5h 04m
United Airlines
Deal found 2/9![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:30 am
PWM
- MSN
2 stops12h 19m
Delta
Tue 4/282:57 pm
MSN
- PWM
1 stop7h 27m
Delta
Deal found 2/8![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
PWM
- MSP
1 stop7h 43m
American Airlines
Sat 3/217:40 am
MSP
- PWM
1 stop14h 54m
American Airlines
Deal found 2/8![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:13 pm
PWM
- MKE
1 stop4h 55m
Delta
Sat 3/77:00 am
MKE
- PWM
1 stop5h 43m
Delta
Deal found 2/9![Delta logo]()
$380
Last-minute flights from Portland to WisconsinDiscover last-minute flight deals from Portland to Wisconsin. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Wisconsin. Data last updated February 12, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
PWM
- ORD
1 stop8h 15m
United Airlines
Thu 3/52:35 pm
ORD
- PWM
1 stop7h 16m
United Airlines
Deal found 2/9![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 am
PWM
- ORD
2 stops12h 10m
Delta
Thu 3/57:00 am
ORD
- PWM
1 stop5h 43m
Delta
Deal found 2/9![Delta logo]()
$254
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/44:16 pm
MSN
- PWM
1 stop6h 34m
American Airlines
Deal found 2/10![American Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:15 pm
PWM
- ORD
Nonstop3h 12m
United Airlines
Wed 3/411:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/9![United Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:45 am
PWM
- GRB
1 stop5h 05m
United Airlines
Mon 3/23:05 pm
GRB
- PWM
1 stop5h 04m
United Airlines
Deal found 2/9![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/55:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Sun 3/88:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/10![American Airlines logo]()
$248
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/66:00 am
PWM
- ORD
1 stop7h 00m
United Airlines
Wed 3/1111:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/11![United Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/65:59 pm
PWM
- ORD
1 stop5h 06m
Delta
Wed 3/111:57 pm
ORD
- PWM
2 stops8h 15m
Delta
Deal found 2/11![Delta logo]()
$244
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/104:23 pm
PWM
- ORD
Nonstop3h 12m
United Airlines
Tue 3/173:40 pm
ORD
- PWM
1 stop6h 24m
United Airlines
Deal found 2/10![United Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/113:44 pm
PWM
- ORD
1 stop8h 29m
United Airlines
Sat 3/1411:48 am
ORD
- PWM
Nonstop2h 26m
United Airlines
Deal found 2/10![United Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/117:00 am
PWM
- ORD
1 stop6h 16m
American Airlines
Sat 3/148:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/11![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:17 am
PWM
- ORD
Nonstop3h 17m
American Airlines
Sat 3/218:02 pm
ORD
- PWM
Nonstop2h 32m
American Airlines
Deal found 2/9![American 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 12, 2026.
Search for one-way flight options from Portland to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 6/2612:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$108
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/102:30 pm
PWM
- ORD
1 stop8h 19m
Delta
Deal found 2/9![Delta logo]()
$115
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/105:40 pm
PWM
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/11![American Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:01 pm
PWM
- ORD
1 stop26h 42m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:46 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$118
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/712:45 pm
PWM
- ORD
2 stops12h 11m
Delta
Deal found 2/11![Delta logo]()
$125
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:36 pm
PWM
- MSP
1 stop5h 48m
American Airlines
Deal found 2/9![American Airlines logo]()
$130
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 am
PWM
- MSP
2 stops9h 48m
United Airlines
Deal found 2/10![United Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/95:48 pm
PWM
- ORD
1 stop5h 24m
Delta
Deal found 2/12![Delta logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Sun 6/1412:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2512:40 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$139
This Priceline deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 8/1012:46 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$144
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Cheapflightsfares) |
One-way from | $89 (Sun Country Air) |
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 12, 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
Thu 6/11
4:58 pm-6:58 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 6/14
6:25 pm-9:58 pm
Nonstop2h 33m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 3/21
6:17 am-8:34 am
Nonstop3h 17m
Chicago O'Hare Intl
Fri 3/27
8:02 pm-11:34 pm
Nonstop2h 32m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 6/5
4:58 pm-6:58 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 6/7
6:25 pm-9:58 pm
Nonstop2h 33m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/2
11:34 am-1:38 pm
Nonstop3h 04m
Chicago O'Hare Intl
Wed 5/6
5:56 pm-9:19 pm
Nonstop2h 23m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/4
6:25 pm-8:34 pm
Nonstop3h 09m
Chicago O'Hare Intl
Sun 6/7
6:25 pm-9:58 pm
Nonstop2h 33m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 6/19
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 6/21
6:25 pm-9:58 pm
Nonstop2h 33m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 3/11
4:23 pm-6:35 pm
Nonstop3h 12m
Chicago O'Hare Intl
Wed 3/18
11:48 am-3:14 pm
Nonstop2h 26m
$209
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 4/1
6:13 pm-8:23 pm
Nonstop3h 10m
Chicago O'Hare Intl
Sat 4/4
1:00 pm-7:01 pm
1 stop5h 01m
$219
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 6/2
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sat 6/6
3:47 pm-11:50 pm
1 stop7h 03m
$219
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 4/21
3:39 pm-9:25 pm
1 stop6h 46m
Madison Truax Field
Tue 4/28
8:00 am-3:09 pm
1 stop6h 09m
$279
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-MSN
PWM-GRB
PWM-MSP
PWM-MKE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Wisconsin
PWM-USWI
PWM-ORD
PWM-MSN
PWM-GRB
PWM-MSP
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 12, 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.
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
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 12, 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 12, 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$391 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$311 | Average$396 | FlexibilityNo cancel fee | On-time63% |