$85+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jul 24 — Jul 311
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 June 24, 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 June 24, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Wed 8/196:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 6/23![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/88:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 7/137:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/21![United Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/98:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Wed 7/1510:30 am
ORD
- BOS
Nonstop2h 37m
United Airlines
Deal found 6/22![United Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/142:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Sat 7/181:09 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/22![JetBlue logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 7/216:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/24![JetBlue logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Tue 7/72:45 pm
BOS
- ORD
1 stop7h 18m
JetBlue
Tue 7/149:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Deal found 6/22![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 8/510:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/23![Delta logo]()
$183
This Super.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:01 am
BOS
- ORD
1 stop4h 44m
JetBlue
Wed 9/91:00 pm
ORD
- BOS
1 stop6h 02m
JetBlue
Deal found 6/22![JetBlue logo]()
$184
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Sun 8/307:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Thu 9/107:05 pm
ORD
- BOS
Nonstop2h 42m
Delta
Deal found 6/21![Delta logo]()
$186
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/98:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 7/196:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 6/22![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/2210:49 am
BOS
- MKE
1 stop7h 28m
American Airlines
Wed 7/2912:52 pm
MKE
- BOS
1 stop7h 18m
American Airlines
Deal found 6/19![American Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/87:19 am
BOS
- MKE
1 stop6h 29m
United Airlines
Wed 7/157:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 6/20![United Airlines logo]()
$197
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 June 24, 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 June 24, 2026.
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/78:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Fri 7/107:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/19![United Airlines logo]()
$178
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/78:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 7/87:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 6/19![Delta logo]()
$191
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Mon 8/314:39 pm
BOS
- ORD
1 stop6h 19m
JetBlue
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/22![JetBlue logo]()
$192
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/283:35 pm
BOS
- MKE
1 stop6h 05m
Southwest
Mon 8/317:00 am
MKE
- BOS
2 stops6h 55m
Southwest
Deal found 6/23![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/238:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 7/286:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 6/22![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 8/67:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/24![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Fri 7/316:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/21![Delta logo]()
$191
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Sat 7/189:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/23![United Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/138:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Sat 7/184:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Deal found 6/22![Delta logo]()
$191
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 8/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/20![United Airlines logo]()
$208
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 8/106:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/24![United Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Mon 8/107:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/24![Delta logo]()
$211
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Mon 8/107:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/21![Delta logo]()
$211
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:40 pm
PWM
- ORD
1 stop7h 23m
JetBlue
Mon 7/136:00 am
ORD
- PWM
1 stop6h 45m
JetBlue
Deal found 6/23![JetBlue logo]()
$327
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:25 pm
PWM
- MKE
2 stops8h 40m
Southwest
Mon 10/55:10 am
MKE
- PWM
1 stop5h 55m
Southwest
Deal found 6/20![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:20 pm
BOS
- MKE
Nonstop2h 52m
Delta
Mon 8/246:00 am
MKE
- BOS
1 stop5h 22m
Delta
Deal found 6/22![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/164:25 pm
BOS
- MKE
Nonstop2h 52m
Delta
Sat 7/184:57 pm
MKE
- BOS
1 stop6h 02m
Delta
Deal found 6/19![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Tue 8/1810:50 am
BOS
- MSP
2 stops8h 50m
Southwest
Thu 8/204:40 pm
MSP
- BOS
1 stop4h 50m
Southwest
Deal found 6/22![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/86:00 am
BOS
- MKE
1 stop7h 48m
United Airlines
Fri 7/101:30 pm
MKE
- BOS
2 stops9h 29m
United Airlines
Deal found 6/21![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/233:55 pm
BOS
- MSP
2 stops8h 25m
Southwest
Wed 7/295:45 am
MSP
- BOS
1 stop7h 00m
Southwest
Deal found 6/22![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/315:30 am
BOS
- MKE
1 stop4h 09m
Delta
Tue 8/46:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 6/22![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/156:00 pm
BOS
- MKE
1 stop6h 37m
United Airlines
Sat 8/227:18 am
MKE
- BOS
2 stops11h 01m
United Airlines
Deal found 6/20![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:15 pm
BOS
- MSP
2 stops8h 05m
Southwest
Sun 8/165:05 am
MSP
- BOS
1 stop5h 20m
Southwest
Deal found 6/23![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:30 am
BOS
- MKE
1 stop4h 09m
Delta
Wed 8/511:31 am
MKE
- BOS
Nonstop2h 28m
Delta
Deal found 6/24![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:30 am
BOS
- MSP
2 stops8h 20m
Southwest
Sat 8/296:00 am
MSP
- BOS
2 stops8h 50m
Southwest
Deal found 6/23![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/316:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Tue 8/47:50 am
MKE
- BOS
2 stops10h 24m
United Airlines
Deal found 6/21![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:40 am
BOS
- MKE
1 stop4h 12m
Delta
Mon 9/218:11 am
MKE
- BOS
1 stop5h 31m
Delta
Deal found 6/20![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/156:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Wed 8/1911:00 am
ORD
- PWM
Nonstop2h 34m
United Airlines
Deal found 6/19![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/84:25 pm
BOS
- MKE
Nonstop2h 52m
Delta
Fri 7/106:40 pm
MKE
- BOS
1 stop4h 19m
Delta
Deal found 6/22![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:10 am
BOS
- MSP
1 stop8h 00m
Southwest
Wed 7/223:50 pm
MSP
- BOS
1 stop4h 35m
Southwest
Deal found 6/23![Southwest logo]()
$417
Last-minute flights from Maine to WisconsinDiscover last-minute flight deals from Maine to Wisconsin. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Wisconsin. Data last updated June 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/17:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Sat 8/297:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/21![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/27:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Tue 9/110:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/21![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/412:00 pm
BOS
- ORD
Nonstop2h 56m
Delta
Mon 8/317:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/20![Delta logo]()
$178
This JetBlue deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Sat 7/411:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Wed 9/29:39 am
ORD
- BOS
1 stop6h 36m
JetBlue
Deal found 6/20![JetBlue logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Sat 7/411:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Tue 7/78:21 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/20![JetBlue logo]()
$183
This JetBlue deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Sat 7/411:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Mon 8/316:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Deal found 6/20![JetBlue logo]()
$188
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/48:58 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Sun 7/56:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 6/20![American Airlines logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Sat 7/411:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Wed 7/156:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 6/22![JetBlue logo]()
$204
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/87:19 am
BOS
- MKE
1 stop6h 29m
United Airlines
Wed 7/157:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 6/20![United Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:16 am
PWM
- MSP
Nonstop3h 09m
Sun Country Air
Mon 7/137:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 6/23![Sun Country Air logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/167:19 am
BOS
- MKE
1 stop6h 29m
United Airlines
Sat 7/185:29 pm
MKE
- BOS
1 stop4h 52m
United Airlines
Deal found 6/19![United Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/2210:49 am
BOS
- MKE
1 stop7h 28m
American Airlines
Wed 7/2912:52 pm
MKE
- BOS
1 stop7h 18m
American Airlines
Deal found 6/19![American Airlines logo]()
$196
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 June 24, 2026.
Search for one-way flight options from Maine to Wisconsin. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:25 pm
PWM
- ORD
1 stop5h 10m
JetBlue
Deal found 6/23![JetBlue logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm
PWM
- ORD
1 stop8h 18m
JetBlue
Deal found 6/22![JetBlue logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/208:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 6/21![JetBlue logo]()
$97
This Super.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:41 pm
PWM
- MSP
Nonstop3h 12m
Sun Country Air
Deal found 6/19![Sun Country Air logo]()
$98
This JetBlue deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/1611:25 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/22![JetBlue logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 6/24![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:40 pm
PWM
- ORD
1 stop8h 18m
JetBlue
Deal found 6/23![JetBlue logo]()
$101
This Super.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:10 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 6/24![JetBlue logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Sat 9/198:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/21![JetBlue logo]()
$103
This Super.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/20![JetBlue logo]()
$103
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 6/23![Delta logo]()
$104
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$105
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 June 24, 2026.
Round-trip from | $177 (Cheapflightsfares) |
|---|---|
One-way from | $85 (JetBlue) |
Popular in | August |
Cheapest in | November |
Average price | $517 |
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 June 24, 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
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Fri 7/10
7:45 pm-11:21 pm
Nonstop2h 36m
$178
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/23
8:15 pm-10:15 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 7/28
6:00 am-11:16 am
1 stop4h 16m
$180
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 7/8
7:25 pm-11:00 pm
Nonstop2h 35m
$191
Quickest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/31
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Thu 8/6
7:30 pm-11:00 pm
Nonstop2h 30m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 7/26
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Fri 7/31
6:59 am-10:30 am
Nonstop2h 31m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/13
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Sat 7/18
4:30 pm-8:11 pm
Nonstop2h 41m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 8/31
4:39 pm-9:58 pm
1 stop6h 19m
Chicago O'Hare Intl
Sat 9/12
8:24 pm-11:58 pm
Nonstop2h 34m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 7/11
7:27 pm-11:31 pm
1 stop5h 04m
Chicago O'Hare Intl
Sat 7/18
9:41 pm-1:14 am
Nonstop2h 33m
$199
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/6
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sun 8/9
9:41 pm-1:14 am
Nonstop2h 33m
$208
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/6
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 8/10
6:20 pm-9:56 pm
Nonstop2h 36m
$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-ORD
BOS-MKE
PWM-MSP
PWM-ORD
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 Maine to Wisconsin
USME-USWI
BOS-ORD
BOS-MKE
PWM-MSP
PWM-ORD
What is the cheapest month to book a flight from Maine to Wisconsin?
Currently, July is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $177). 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 June 24, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 June 24, 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 June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$414 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$420 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$445 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$358 | Average$399 | FlexibilityNo cancel fee | On-time63% |