$88+ Cheap flights from Maine 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
Jun 16 — Jun 231
Round-trip
1 adult, Economy
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Cheapest flights from Maine to WisconsinExplore the most affordable flight options available from Maine to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.
Explore the most affordable flight options available from Maine to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.
This SmartFares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/15![JetBlue logo]()
$173
This SmartFares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sun 5/318:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:00 pm
BOS
- MKE
1 stop5h 34m
United Airlines
Fri 6/55:39 pm
MKE
- BOS
1 stop4h 42m
United Airlines
Deal found 5/13![United Airlines logo]()
$187
This JetBlue deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$187
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 6/312:01 pm
BOS
- ORD
1 stop8h 28m
Multiple Airlines
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$189
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
BOS
- MKE
1 stop6h 13m
Frontier
Wed 6/2412:08 pm
MKE
- BOS
1 stop12h 19m
Frontier
Deal found 5/13![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:12 am
BOS
- ORD
1 stop11h 43m
Frontier
Wed 8/261:50 pm
ORD
- BOS
1 stop10h 37m
Frontier
Deal found 5/12![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sat 6/61:55 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$191
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/37:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 5/13![United Airlines logo]()
$192
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Wed 6/101:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 6/26:00 am
BOS
- ORD
1 stop14h 29m
Frontier
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/13![Frontier logo]()
$195
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
BOS
- MKE
1 stop6h 15m
Frontier
Sat 8/112:10 pm
MKE
- BOS
1 stop12h 13m
Frontier
Deal found 5/12![Frontier logo]()
$200
Best flights from Maine to WisconsinDiscover carefully curated flight deals from Maine to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 17, 2026.
Discover carefully curated flight deals from Maine to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 17, 2026.
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/273:08 pm
BOS
- MKE
1 stop4h 43m
United Airlines
Sat 5/305:29 pm
MKE
- BOS
1 stop4h 52m
United Airlines
Deal found 5/12![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/27:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Mon 6/87:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 5/13![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 5/277:35 am
BOS
- ORD
2 stops9h 30m
Southwest
Fri 5/292:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Deal found 5/14![Southwest logo]()
$231
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:25 pm
BGR
- ORD
1 stop6h 26m
American Airlines
Tue 7/288:30 am
ORD
- BGR
1 stop6h 54m
American Airlines
Deal found 5/16![American Airlines logo]()
$281
This Sun Country Air deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Tue 8/411:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Mon 8/105:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 5/16![Sun Country Air logo]()
$338
This JetBlue deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/92:37 pm
PWM
- ORD
1 stop9h 21m
JetBlue
Wed 6/103:39 pm
ORD
- PWM
1 stop7h 19m
JetBlue
Deal found 5/16![JetBlue logo]()
$351
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:38 am
BOS
- MKE
1 stop4h 55m
United Airlines
Sat 9/126:00 am
MKE
- BOS
1 stop5h 47m
United Airlines
Deal found 5/16![United Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 6/26:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/13![United Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/309:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Tue 6/27:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/16![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/35:40 am
BOS
- MKE
1 stop4h 09m
Delta
Sun 6/77:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 5/17![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/45:40 am
BOS
- MKE
1 stop4h 09m
Delta
Sun 6/77:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 5/13![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/58:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 8/159:00 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 5/16![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/166:00 am
BOS
- MKE
1 stop5h 05m
Delta
Tue 6/237:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 5/17![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/229:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 7/266:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/13![United Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:24 pm
PWM
- ORD
Nonstop3h 06m
American Airlines
Sat 7/184:45 pm
ORD
- PWM
1 stop5h 03m
American Airlines
Deal found 5/12![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Tue 6/27:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/16![United Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 8/155:30 am
BOS
- MKE
1 stop4h 09m
Delta
Sat 8/154:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Deal found 5/12![Delta logo]()
$247
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/107:19 am
BGR
- ORD
1 stop5h 50m
American Airlines
Wed 6/178:05 am
ORD
- BGR
Nonstop2h 35m
American Airlines
Deal found 5/16![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/176:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Sun 7/199:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/14![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/15:30 am
BOS
- MKE
1 stop4h 21m
Delta
Sun 7/56:00 am
MKE
- BOS
1 stop7h 24m
Delta
Deal found 5/15![Delta logo]()
$257
This Sun Country Air deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:46 pm
PWM
- MSP
Nonstop3h 08m
Sun Country Air
Mon 8/178:05 am
MSP
- PWM
Nonstop2h 39m
Sun Country Air
Deal found 5/16![Sun Country Air logo]()
$398
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 9/231:05 pm
PWM
- MSP
2 stops9h 55m
Southwest
Wed 9/307:15 am
MSP
- PWM
2 stops9h 00m
Southwest
Deal found 5/16![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:00 pm
BOS
- ORD
1 stop5h 30m
United Airlines
Sat 5/303:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 5/16![United Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/25:30 am
BOS
- MKE
1 stop4h 21m
Delta
Mon 7/67:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 5/16![Delta logo]()
$257
This American Airlines deal was found by Cheapflights users on 5/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 pm
PWM
- ORD
1 stop7h 01m
American Airlines
Sat 7/184:45 pm
ORD
- PWM
1 stop5h 03m
American Airlines
Deal found 5/12![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:10 am
BOS
- MKE
Nonstop2h 41m
Delta
Fri 8/146:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 5/13![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/268:00 pm
BOS
- MSP
1 stop5h 50m
Southwest
Tue 6/305:25 am
MSP
- BOS
2 stops7h 20m
Southwest
Deal found 5/14![Southwest logo]()
$424
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/57:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Mon 6/89:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/16![United Airlines logo]()
$229
This Sun Country Air deal was found by Cheapflights users on 5/12. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:39 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Sun 5/316:55 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Deal found 5/12![Sun Country Air logo]()
$448
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/242:25 pm
BOS
- MSP
2 stops9h 20m
Southwest
Thu 7/26:00 pm
MSP
- BOS
1 stop5h 05m
Southwest
Deal found 5/14![Southwest logo]()
$424
Last-minute flights from Maine to WisconsinDiscover last-minute flight deals from Maine to Wisconsin. Data last updated May 17, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Wisconsin. Data last updated May 17, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sun 5/318:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:00 pm
BOS
- MKE
1 stop5h 34m
United Airlines
Fri 6/55:39 pm
MKE
- BOS
1 stop4h 42m
United Airlines
Deal found 5/13![United Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Wed 6/109:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/12![United Airlines logo]()
$192
This SmartFares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/15![JetBlue logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 6/26:00 am
BOS
- ORD
1 stop14h 29m
Frontier
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/13![Frontier logo]()
$195
This JetBlue deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$187
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 6/312:01 pm
BOS
- ORD
1 stop8h 28m
Multiple Airlines
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sat 6/61:55 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$191
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Wed 6/101:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$194
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:10 am
BOS
- ORD
1 stop11h 40m
Frontier
Tue 6/231:29 pm
ORD
- BOS
1 stop10h 58m
Frontier
Deal found 5/13![Frontier logo]()
$190
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
BOS
- MKE
1 stop6h 13m
Frontier
Wed 6/2412:08 pm
MKE
- BOS
1 stop12h 19m
Frontier
Deal found 5/13![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/196:00 am
BOS
- MKE
1 stop6h 13m
Frontier
Wed 6/2412:08 pm
MKE
- BOS
1 stop12h 19m
Frontier
Deal found 5/13![Frontier logo]()
$200
One-way flights from Maine to WisconsinSearch for one-way flight options from Maine to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 17, 2026.
Search for one-way flight options from Maine to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 5/2712:01 pm
BOS
- ORD
1 stop20h 54m
Frontier
Deal found 5/13![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$91
This Super.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/17![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/15![JetBlue logo]()
$93
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/65:05 pm
BOS
- MKE
1 stop7h 42m
American Airlines
Deal found 5/13![American Airlines logo]()
$94
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/97:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 5/13![Delta logo]()
$94
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
BOS
- MKE
1 stop6h 13m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Frontier
Deal found 5/13![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/16![JetBlue logo]()
$96
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 5/12. 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.
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/12![JetBlue logo]()
$98
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 5/305:45 am
BOS
- MKE
2 stops6h 34m
United Airlines
Deal found 5/13![United Airlines logo]()
$99
Find flight deals from Maine to Wisconsin
Keep the following information in mind while searching for Maine to Wisconsin flight deals. Data was last updated May 17, 2026.
Round-trip from | $173 (SmartFares) |
|---|---|
One-way from | $88 (Kiwi.com) |
Popular in | September |
Cheapest in | November |
Average price | $442 |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine 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 May 17, 2026.
Use the filters below to find and compare flights from Maine to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 5/27
3:08 pm-6:51 pm
1 stop4h 43m
Milwaukee-Mitchell
Sat 5/30
5:29 pm-11:21 pm
1 stop4h 52m
$187
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 9/9
10:38 am-2:33 pm
1 stop4h 55m
Milwaukee-Mitchell
Sat 9/12
6:00 am-12:47 pm
1 stop5h 47m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Mon 6/8
7:25 pm-11:02 pm
Nonstop2h 37m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/31
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 6/2
6:05 am-9:29 am
Nonstop2h 24m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/30
9:50 am-11:43 am
Nonstop2h 53m
Chicago O'Hare Intl
Tue 6/2
7:45 pm-11:21 pm
Nonstop2h 36m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/5
8:20 pm-10:20 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sat 8/15
9:00 pm-12:34 am
Nonstop2h 34m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/22
9:50 am-11:43 am
Nonstop2h 53m
Chicago O'Hare Intl
Sun 7/26
6:05 am-9:29 am
Nonstop2h 24m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/1
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Tue 6/2
7:45 pm-11:21 pm
Nonstop2h 36m
$202
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/17
6:43 pm-8:40 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 7/19
9:41 pm-1:14 am
Nonstop2h 33m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/24
7:00 pm-11:30 pm
1 stop5h 30m
Chicago O'Hare Intl
Sat 5/30
3:55 pm-7:30 pm
Nonstop2h 35m
$211
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maine to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Maine with our price prediction graph.
BOS-MKE
BOS-ORD
BOS-ATW
PWM-ORD
BOS-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 Maine to Wisconsin
USME-USWI
BOS-MKE
BOS-ORD
BOS-ATW
PWM-ORD
What is the cheapest month to book a flight from Maine to Wisconsin?
Currently, December is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $193). Flying from Maine to Wisconsin in March is currently the most expensive (average of $329). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Maine to Wisconsin?
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated May 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Maine to Wisconsin by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Maine to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Maine to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Wisconsin by cabin class
Find flights from Maine to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Wisconsin flights
Browse other Maine and Wisconsin flight options. Last updated on May 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Wisconsin
Find the right flight back to Maine after your stay in Wisconsin
Maine to Wisconsin flights
Consider these flights traveling from Maine to Wisconsin.
Top 4 airlines flying from Maine to Wisconsin
Discover the top 4 airlines that operate flights from Maine 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 May 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$423 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$477 | FlexibilityNo cancel fee | On-time63% |