$84+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jun 9 — Jun 161
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Wisconsin with Cheapflights
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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 10, 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 10, 2026.
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/87:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 5/5![Delta logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/29:12 am
BOS
- ORD
1 stop23h 43m
Frontier
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/6![Frontier logo]()
$169
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/307:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/177:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Sat 6/206:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 5/6![American Airlines logo]()
$173
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/235:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 5/276:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/6![United Airlines logo]()
$177
This SmartFares deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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.
Fri 7/245:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 7/2810:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/6![JetBlue logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/88:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Fri 7/1010:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/5![JetBlue logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Sat 6/68:41 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 5/5![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/317:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/9![Delta logo]()
$183
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/305:05 am
BOS
- ORD
Nonstop2h 57m
American Airlines
Sun 5/316:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 5/7![American Airlines logo]()
$184
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/39:50 am
BOS
- MKE
1 stop5h 46m
United Airlines
Sat 6/61:30 pm
MKE
- BOS
1 stop5h 00m
United Airlines
Deal found 5/7![United Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
- ORD
1 stop4h 51m
United Airlines
Tue 6/26:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/7![United Airlines logo]()
$187
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 10, 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 10, 2026.
This JetBlue deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/5![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/275:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Fri 5/296:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/5![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/317:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/9![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 am
BOS
- MKE
2 stops7h 30m
Southwest
Mon 6/15:50 am
MKE
- BOS
1 stop5h 50m
Southwest
Deal found 5/8![Southwest logo]()
$232
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 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 5/9![American Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:00 pm
BOS
- ORD
1 stop5h 30m
United Airlines
Sat 5/303:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 5/9![United Airlines logo]()
$187
This Sun Country Air deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Thu 7/231:16 pm
PWM
- MSP
Nonstop3h 11m
Sun Country Air
Sat 7/257:55 am
MSP
- PWM
Nonstop2h 42m
Sun Country Air
Deal found 5/5![Sun Country Air logo]()
$378
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Mon 7/137:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 5/8![Delta logo]()
$201
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Sat 6/131:55 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 5/8![United Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/108:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Mon 7/137:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 5/7![Delta logo]()
$205
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 8/15:10 am
BOS
- MKE
1 stop5h 15m
Southwest
Fri 8/75:00 pm
MKE
- BOS
1 stop4h 10m
Southwest
Deal found 5/6![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:15 pm
BOS
- ORD
Nonstop3h 05m
Delta
Sat 6/134:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Deal found 5/9![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am
BOS
- ORD
Nonstop2h 50m
United Airlines
Tue 9/297:15 am
ORD
- BOS
1 stop4h 32m
United Airlines
Deal found 5/9![United Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/307:20 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 5/9![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:50 pm
BOS
- MKE
1 stop5h 05m
Southwest
Tue 8/46:40 am
MKE
- BOS
2 stops8h 20m
Southwest
Deal found 5/8![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:00 am
BOS
- MKE
1 stop5h 54m
Delta
Tue 6/26:55 pm
MKE
- BOS
Nonstop2h 21m
Delta
Deal found 5/8![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
BOS
- ATW
1 stop8h 33m
American Airlines
Tue 6/306:28 pm
ATW
- BOS
1 stop5h 00m
American Airlines
Deal found 5/4![American Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/135:45 am
BOS
- ORD
1 stop4h 48m
United Airlines
Fri 8/149:30 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 5/5![United Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/264:45 pm
BOS
- MKE
Nonstop2h 50m
Delta
Mon 6/297:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 5/6![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:45 pm
BOS
- ATW
1 stop7h 24m
American Airlines
Fri 6/122:03 pm
ATW
- BOS
1 stop5h 56m
American Airlines
Deal found 5/9![American Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/225:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Sun 5/247:10 am
MKE
- BOS
1 stop7h 55m
Southwest
Deal found 5/6![Southwest logo]()
$302
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:02 pm
PWM
- ORD
1 stop7h 31m
American Airlines
Tue 6/98:00 am
ORD
- PWM
Nonstop2h 29m
American Airlines
Deal found 5/9![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/235:30 am
BOS
- MKE
1 stop4h 20m
Delta
Tue 7/286:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 5/7![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:35 am
BOS
- MKE
1 stop4h 50m
Southwest
Tue 8/46:40 am
MKE
- BOS
2 stops8h 20m
Southwest
Deal found 5/9![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:45 am
BOS
- MKE
2 stops6h 34m
United Airlines
Sat 5/3012:05 pm
MKE
- BOS
1 stop6h 25m
United Airlines
Deal found 5/9![United Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:22 am
BOS
- GRB
2 stops7h 57m
American Airlines
Wed 6/1012:59 pm
GRB
- BOS
2 stops8h 29m
American Airlines
Deal found 5/4![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 8/410:50 am
BOS
- MKE
2 stops10h 05m
Southwest
Sun 8/95:45 am
MKE
- BOS
2 stops5h 55m
Southwest
Deal found 5/6![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:45 am
BOS
- MKE
2 stops9h 51m
United Airlines
Sat 6/131:30 pm
MKE
- BOS
1 stop7h 26m
United Airlines
Deal found 5/9![United Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:22 pm
BGR
- ORD
1 stop6h 30m
Delta
Tue 7/281:44 pm
ORD
- BGR
2 stops8h 27m
Delta
Deal found 5/9![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
BOS
- ATW
1 stop6h 53m
United Airlines
Sat 8/295:00 pm
ATW
- BOS
1 stop6h 34m
United Airlines
Deal found 5/8![United Airlines logo]()
$301
Last-minute flights from Maine to WisconsinDiscover last-minute flight deals from Maine to Wisconsin. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Wisconsin. Data last updated May 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/198:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Wed 5/277:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/5![Delta logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$182
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/1910:32 am
BOS
- ORD
Nonstop3h 08m
American Airlines
Wed 5/203:15 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 5/5![American Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/1911:00 am
BOS
- MKE
1 stop7h 04m
Delta
Wed 5/2011:33 am
MKE
- BOS
Nonstop2h 26m
Delta
Deal found 5/5![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/199:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 5/205:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Deal found 5/5![United Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/195:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Fri 5/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/5![United Airlines logo]()
$206
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/233:08 pm
BOS
- MKE
1 stop4h 43m
United Airlines
Tue 5/266:14 am
MKE
- BOS
1 stop5h 58m
United Airlines
Deal found 5/5![United Airlines logo]()
$203
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Sat 6/68:41 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 5/5![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/39:50 am
BOS
- MKE
1 stop5h 46m
United Airlines
Sat 6/61:30 pm
MKE
- BOS
1 stop5h 00m
United Airlines
Deal found 5/7![United Airlines logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/36:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Wed 6/108:41 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 5/6![JetBlue logo]()
$202
This Expedia deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/36:15 am
BOS
- MKE
Nonstop2h 36m
Multiple Airlines
Wed 6/1012:08 pm
MKE
- BOS
1 stop12h 19m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$204
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/106:15 am
BOS
- MKE
Nonstop2h 36m
Multiple Airlines
Wed 6/2412:08 pm
MKE
- BOS
1 stop12h 19m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$194
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 10, 2026.
Search for one-way flight options from Maine to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/9![Delta logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 stop8h 40m
Frontier
Deal found 5/6![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/5![JetBlue logo]()
$87
This JetBlue deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/7![JetBlue logo]()
$89
This SmartFares deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/8![JetBlue logo]()
$90
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/46:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 5/5![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 5/9![JetBlue logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/26:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 5/5![JetBlue logo]()
$93
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
BOS
- MKE
1 stop4h 57m
United Airlines
Deal found 5/8![United Airlines logo]()
$94
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/235:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/7![United Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 8/56:00 am
BOS
- MKE
1 stop6h 15m
Frontier
Deal found 5/6![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/2212:04 pm
BOS
- ORD
1 stop8h 49m
Frontier
Deal found 5/5![Frontier logo]()
$95
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 10, 2026.
Round-trip from | $167 (Delta) |
|---|---|
One-way from | $84 (Delta) |
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 10, 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 6/2
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 6/8
8:30 pm-11:59 pm
Nonstop2h 29m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/27
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Fri 5/29
6:20 pm-9:56 pm
Nonstop2h 36m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/30
5:30 pm-7:33 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 5/31
7:00 am-10:35 am
Nonstop2h 35m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/26
7:00 pm-11:30 pm
1 stop5h 30m
Chicago O'Hare Intl
Sat 5/30
3:55 pm-7:30 pm
Nonstop2h 35m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Mon 7/13
7:05 am-10:36 am
Nonstop2h 31m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/12
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Sat 6/13
1:55 pm-5:29 pm
Nonstop2h 34m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/10
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Mon 7/13
7:05 am-10:36 am
Nonstop2h 31m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/12
4:15 pm-6:20 pm
Nonstop3h 05m
Chicago O'Hare Intl
Sat 6/13
4:30 pm-8:11 pm
Nonstop2h 41m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 9/25
6:00 am-7:50 am
Nonstop2h 50m
Chicago O'Hare Intl
Tue 9/29
7:15 am-12:47 pm
1 stop4h 32m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/27
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 8/30
7:20 am-10:54 am
Nonstop2h 34m
$215
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-ORD
BOS-MSP
BOS-GRB
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-ORD
BOS-MSP
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 10, 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
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
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 10, 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 10, 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% |