$96+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Aug 23 — Aug 301
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Maine 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Maine to Wisconsin
Cheapest
Best
Last-minute
One-way
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 July 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 July 24, 2026.
This Flysmarter deal was found by Cheapflights users on 7/21. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Sun 9/136:20 am
ORD
- BOS
1 stop6h 24m
JetBlue
Deal found 7/21![JetBlue logo]()
$188
This Super.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/1212:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Sat 8/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This SmartFares deal was found by Cheapflights users on 7/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 8/126:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/20![JetBlue logo]()
$194
This SmartFares deal was found by Cheapflights users on 7/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Wed 9/231:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/21![JetBlue logo]()
$195
This Super.com deal was found by Cheapflights users on 7/19. 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.
Thu 10/156:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Tue 10/208:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/19![JetBlue logo]()
$197
This Flysmarter deal was found by Cheapflights users on 7/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/20![JetBlue logo]()
$198
This Super.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/227:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/20![JetBlue logo]()
$205
This JetBlue deal was found by Cheapflights users on 7/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Wed 9/1611:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Deal found 7/19![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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 8/187:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Tue 8/259:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/22![JetBlue logo]()
$215
This Delta deal was found by Cheapflights users on 7/23. 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.
Wed 9/309:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Sat 10/32:35 pm
MKE
- BOS
Nonstop2h 32m
Delta
Deal found 7/23![Delta logo]()
$217
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 July 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 July 24, 2026.
This JetBlue deal was found by Cheapflights users on 7/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Wed 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/21![JetBlue logo]()
$211
This Delta deal was found by Cheapflights users on 7/23. 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.
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Wed 9/237:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/23![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Mon 10/197:01 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Fri 10/237:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/20![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:20 pm
BOS
- MKE
1 stop7h 15m
Southwest
Mon 9/145:45 am
MKE
- BOS
1 stop4h 55m
Southwest
Deal found 7/21![Southwest logo]()
$237
This Sun Country Air deal was found by Cheapflights users on 7/21. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:25 pm
PWM
- MSP
Nonstop3h 03m
Sun Country Air
Mon 8/318:15 am
MSP
- PWM
Nonstop2h 41m
Sun Country Air
Deal found 7/21![Sun Country Air logo]()
$258
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
BGR
- MSN
2 stops9h 05m
American Airlines
Sat 8/222:45 pm
MSN
- BGR
2 stops8h 14m
American Airlines
Deal found 7/23![American Airlines logo]()
$315
This JetBlue deal was found by Cheapflights users on 7/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Tue 8/2511:01 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 7/21![JetBlue logo]()
$218
This Delta deal was found by Cheapflights users on 7/20. 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 8/2812:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Sun 8/307:30 pm
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 7/20![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/21. 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 8/2112:27 pm
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 8/236:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 7/21![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:30 am
BOS
- MKE
1 stop4h 35m
Southwest
Wed 8/266:40 am
MKE
- BOS
2 stops8h 20m
Southwest
Deal found 7/21![Southwest logo]()
$242
This JetBlue deal was found by Cheapflights users on 7/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Fri 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/19![JetBlue logo]()
$225
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 8/187:00 am
BOS
- MKE
1 stop6h 36m
Delta
Tue 8/256:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/23![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Thu 9/2410:36 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 9/277:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/23![United Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Thu 9/1010:38 am
BOS
- ORD
Nonstop2h 51m
United Airlines
Mon 9/149:40 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Deal found 7/23![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Fri 8/288:00 am
MKE
- BOS
2 stops8h 50m
Southwest
Deal found 7/19![Southwest logo]()
$267
This JetBlue deal was found by Cheapflights users on 7/23. 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 8/127:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Fri 8/149:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/23![JetBlue logo]()
$257
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Fri 10/25:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 10/49:24 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Deal found 7/19![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 7/19. 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.
Fri 9/185:40 am
BOS
- MKE
1 stop4h 08m
Delta
Mon 9/216:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Deal found 7/19![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:40 am
BOS
- MKE
1 stop5h 15m
Southwest
Mon 8/176:25 am
MKE
- BOS
1 stop5h 05m
Southwest
Deal found 7/24![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 7/22. 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 8/56:00 pm
BOS
- MKE
1 stop5h 30m
Delta
Mon 8/176:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/22![Delta logo]()
$272
This Sun Country Air deal was found by Cheapflights users on 7/23. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:33 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Fri 8/215:50 am
MSP
- BOS
Nonstop2h 48m
Sun Country Air
Deal found 7/23![Sun Country Air logo]()
$378
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/66:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 8/86:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:40 am
BOS
- MKE
1 stop5h 15m
Southwest
Mon 9/215:45 am
MKE
- BOS
2 stops7h 45m
Southwest
Deal found 7/21![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 7/20. 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.
Tue 9/299:10 am
BOS
- MKE
1 stop4h 38m
Delta
Sun 10/46:00 am
MKE
- BOS
1 stop7h 24m
Delta
Deal found 7/20![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Wed 10/219:25 am
BGR
- ORD
Nonstop3h 04m
United Airlines
Sat 10/245:52 pm
ORD
- BGR
Nonstop2h 47m
United Airlines
Deal found 7/23![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:25 pm
BOS
- MKE
2 stops9h 40m
Southwest
Mon 12/148:00 am
MKE
- BOS
2 stops8h 05m
Southwest
Deal found 7/19![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 7/22. 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.
Tue 10/276:00 am
BGR
- MSN
1 stop5h 29m
Delta
Tue 11/312:30 pm
MSN
- BGR
1 stop4h 49m
Delta
Deal found 7/22![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Wed 11/44:10 pm
BGR
- MSN
1 stop8h 27m
United Airlines
Sat 11/76:09 am
MSN
- BGR
1 stop7h 49m
United Airlines
Deal found 7/23![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 7/23. 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.
Tue 10/276:00 am
BGR
- MSN
1 stop5h 29m
Delta
Sat 10/3112:30 pm
MSN
- BGR
1 stop4h 49m
Delta
Deal found 7/23![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:35 am
BOS
- MSP
1 stop5h 20m
Southwest
Thu 8/2012:15 pm
MSP
- BOS
1 stop6h 25m
Southwest
Deal found 7/19![Southwest logo]()
$319
Last-minute flights from Maine to WisconsinDiscover last-minute flight deals from Maine to Wisconsin. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Wisconsin. Data last updated July 24, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 7/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 8/126:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/20![JetBlue logo]()
$194
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Tue 8/189:35 am
ORD
- BOS
1 stop8h 22m
JetBlue
Deal found 7/21![JetBlue logo]()
$202
This Super.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/1212:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Sat 8/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/20. 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 8/145:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Mon 8/176:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/20![JetBlue logo]()
$207
This Flysmarter deal was found by Cheapflights users on 7/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/20![JetBlue logo]()
$198
This Super.com deal was found by Cheapflights users on 7/22. 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.
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Tue 8/256:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$201
This Super.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/19![JetBlue logo]()
$206
This Priceline deal was found by Cheapflights users on 7/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/21![JetBlue logo]()
$207
This Super.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/227:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/20![JetBlue logo]()
$205
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Fri 8/285:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/21![JetBlue logo]()
$203
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 July 24, 2026.
Search for one-way flight options from Maine to Wisconsin. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This Super.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/19![JetBlue logo]()
$96
This Super.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/19![JetBlue logo]()
$97
This Super.com deal was found by Cheapflights users on 7/20. 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.
Wed 8/124:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$98
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$99
This Super.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/145:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/22![JetBlue logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 7/21. 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 10/36:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$102
This Super.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/22![JetBlue logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:11 pm
BOS
- ORD
1 stop6h 55m
JetBlue
Deal found 7/19![JetBlue logo]()
$104
This JetBlue deal was found by Cheapflights users on 7/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/19![JetBlue logo]()
$106
This JetBlue deal was found by Cheapflights users on 7/22. 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 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Mon 9/285:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 7/19![JetBlue logo]()
$112
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 July 24, 2026.
Round-trip from | $188 (Flysmarter) |
|---|---|
One-way from | $96 (Super.com) |
Popular in | August |
Cheapest in | November |
Average price | $477 |
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 July 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 8/11
2:45 pm-9:58 pm
1 stop8h 13m
Chicago O'Hare Intl
Wed 8/12
9:35 am-5:17 pm
1 stop6h 42m
$211
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/9
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 9/23
7:30 pm-11:09 pm
Nonstop2h 39m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/18
2:45 pm-9:58 pm
1 stop8h 13m
Chicago O'Hare Intl
Tue 8/25
11:01 am-2:28 pm
Nonstop2h 27m
$218
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 10/19
7:01 am-9:00 am
Nonstop2h 59m
Chicago O'Hare Intl
Fri 10/23
7:30 am-11:04 am
Nonstop2h 34m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/28
12:25 pm-2:19 pm
Nonstop2h 54m
Chicago O'Hare Intl
Sun 8/30
7:30 pm-11:02 pm
Nonstop2h 32m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/21
12:27 pm-2:20 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 8/23
6:15 am-9:36 am
Nonstop2h 21m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/5
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Fri 8/7
8:20 pm-11:51 pm
Nonstop2h 31m
$225
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Tue 8/18
7:00 am-12:36 pm
1 stop6h 36m
Milwaukee-Mitchell
Tue 8/25
6:55 pm-10:22 pm
Nonstop2h 27m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/24
10:36 am-12:29 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:04 am
Nonstop2h 34m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/10
10:38 am-12:29 pm
Nonstop2h 51m
Chicago O'Hare Intl
Mon 9/14
9:40 pm-1:10 am
Nonstop2h 30m
$227
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-MSN
PWM-ORD
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-MSN
What is the cheapest month to book a flight from Maine to Wisconsin?
Currently, November is the cheapest month in which you can book a flight from Maine to Wisconsin (average of $328). Flying from Maine to Wisconsin in December is currently the most expensive (average of $583). 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?
Airfare is below average for this route at the moment.
Maine to Wisconsin flights typically cost between $763 and $973 in August.The cheapest round-trip price found within the last 5 days was $317 on United Airlines (Aug 19-Aug 25).
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 July 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.
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
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 July 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 July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$416 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$311 | Average$399 | FlexibilityNo cancel fee | On-time63% |