$67+ Cheap flights from Massachusetts 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Mar 14 — Mar 211
1 adult, Economy
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Cheapest flights from Massachusetts to WisconsinExplore the most affordable flight options available from Massachusetts to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Massachusetts to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/11![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:45 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Tue 2/246:20 pm
ORD
- BOS
Nonstop2h 28m
United Airlines
Deal found 2/9![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Tue 3/37:18 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 2/9![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:50 pm
BOS
- ORD
Nonstop3h 03m
Delta
Thu 2/267:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 2/9![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/11![Delta logo]()
$138
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Sun 4/57:20 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 2/10![American Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/11![United Airlines logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:32 pm
BOS
- ORD
1 stop6h 27m
JetBlue
Thu 3/1211:00 am
ORD
- BOS
Nonstop2h 24m
JetBlue
Deal found 2/8![JetBlue logo]()
$141
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Mon 3/96:04 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 2/8![JetBlue logo]()
$142
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Tue 3/36:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/10![JetBlue logo]()
$144
This JetBlue deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Mon 3/210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/10![JetBlue logo]()
$145
Best flights from Massachusetts to WisconsinDiscover carefully curated flight deals from Massachusetts to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Massachusetts to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Mon 3/96:04 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 2/8![JetBlue logo]()
$142
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Mon 4/67:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/9![Delta logo]()
$142
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:40 am
BOS
- ORD
Nonstop2h 51m
United Airlines
Fri 7/179:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/9![United Airlines logo]()
$145
This Sun Country Air deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:51 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 7/127:20 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2710:52 am
ALB
- ORD
1 stop25h 35m
Multiple Airlines
Thu 4/308:24 pm
ORD
- ALB
2 stops21h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$235
This CheapOair deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/138:08 pm
BDL
- MKE
1 stop24h 58m
Frontier
Sun 3/157:44 pm
MKE
- BDL
1 stop22h 29m
Frontier
Deal found 2/9![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:25 pm
BOS
- MKE
2 stops14h 20m
Southwest
Wed 5/65:50 am
MKE
- BOS
2 stops7h 00m
Southwest
Deal found 2/10![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Sat 6/139:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/10![United Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:15 am
BOS
- MSN
1 stop5h 20m
American Airlines
Sat 8/86:00 am
MSN
- BOS
1 stop7h 17m
American Airlines
Deal found 2/11![American Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:15 am
BOS
- ORD
Nonstop3h 13m
Delta
Mon 3/27:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 2/11![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/57:25 am
BOS
- ORD
Nonstop3h 10m
Delta
Tue 4/710:40 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 2/11![Delta logo]()
$152
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/211:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 2/9![United Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:00 pm
BOS
- ORD
Nonstop2h 54m
Delta
Tue 5/197:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
Deal found 2/10![Delta logo]()
$152
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Tue 5/56:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 2/11![United Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Sat 5/304:30 pm
ORD
- BOS
Nonstop2h 33m
Delta
Deal found 2/11![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 3/19:17 am
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/9![United Airlines logo]()
$161
This Sun Country Air deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:45 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Tue 4/218:24 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$238
This Sun Country Air deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2811:40 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Thu 7/96:35 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$244
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
BDL
- MKE
1 stop8h 20m
Frontier
Mon 3/28:11 pm
MKE
- BDL
1 stop12h 12m
Frontier
Deal found 2/11![Frontier logo]()
$271
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:45 am
ALB
- ORD
1 stop8h 20m
Southwest
Tue 5/191:35 pm
ORD
- ALB
1 stop8h 15m
Southwest
Deal found 2/10![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:50 pm
BOS
- MKE
Nonstop2h 50m
Delta
Mon 3/237:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/10![Delta logo]()
$207
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:29 pm
BDL
- MSN
1 stop5h 06m
American Airlines
Sun 4/126:20 am
MSN
- BDL
1 stop7h 23m
American Airlines
Deal found 2/10![American Airlines logo]()
$304
This Sun Country Air deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:35 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Wed 4/226:24 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Deal found 2/9![Sun Country Air logo]()
$258
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:50 pm
BOS
- MKE
Nonstop2h 50m
Delta
Mon 3/166:33 pm
MKE
- BOS
1 stop4h 20m
Delta
Deal found 2/9![Delta logo]()
$207
This Sun Country Air deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:40 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Fri 7/105:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 2/10![Sun Country Air logo]()
$264
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:50 pm
BDL
- MKE
1 stop6h 15m
Southwest
Mon 3/235:50 am
MKE
- BDL
1 stop3h 55m
Southwest
Deal found 2/10![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/104:54 pm
BOS
- MKE
1 stop4h 46m
Delta
Wed 3/1112:27 pm
MKE
- BOS
Nonstop2h 17m
Delta
Deal found 2/10![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:45 am
BOS
- MKE
2 stops6h 47m
United Airlines
Wed 4/296:50 am
MKE
- BOS
1 stop4h 56m
United Airlines
Deal found 2/11![United Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/242:35 pm
BDL
- MKE
2 stops8h 40m
Southwest
Thu 3/265:50 am
MKE
- BDL
1 stop3h 55m
Southwest
Deal found 2/10![Southwest logo]()
$334
This Sun Country Air deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:39 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Fri 5/296:55 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Deal found 2/11![Sun Country Air logo]()
$279
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated February 12, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/10![JetBlue logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/10![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:45 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Tue 2/246:20 pm
ORD
- BOS
Nonstop2h 28m
United Airlines
Deal found 2/9![United Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:50 pm
BOS
- ORD
Nonstop3h 03m
Delta
Thu 2/267:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 2/9![Delta logo]()
$137
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/11![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/29:17 am
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/11![United Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Tue 3/37:18 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 2/9![American Airlines logo]()
$136
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Multiple Airlines
Tue 3/1010:00 am
ORD
- BOS
Nonstop2h 20m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$140
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/1112:44 pm
ORD
- BOS
1 stop6h 20m
JetBlue
Deal found 2/8![JetBlue logo]()
$142
This Priceline deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:43 pm
BOS
- ORD
1 stop8h 04m
Multiple Airlines
Fri 3/612:41 pm
ORD
- BOS
1 stop6h 17m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$146
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/99:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/8![United Airlines logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:32 pm
BOS
- ORD
1 stop6h 27m
JetBlue
Thu 3/1211:00 am
ORD
- BOS
Nonstop2h 24m
JetBlue
Deal found 2/8![JetBlue logo]()
$141
One-way flights from Massachusetts to WisconsinSearch for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Super.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/9![JetBlue logo]()
$67
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$68
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:07 pm
BOS
- ORD
1 stop5h 54m
United Airlines
Deal found 2/9![United Airlines logo]()
$69
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:19 am
BDL
- ORD
1 stop25h 27m
Frontier
Deal found 2/10![Frontier logo]()
$70
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$70
This Priceline deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$71
This JetBlue deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
BDL
- ORD
1 stop6h 49m
JetBlue
Deal found 2/9![JetBlue logo]()
$72
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/11![JetBlue logo]()
$72
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:40 am
BOS
- ORD
Nonstop2h 51m
United Airlines
Deal found 2/10![United Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:40 am
BOS
- ORD
1 stop16h 37m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$75
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:10 pm
BOS
- ORD
1 stop18h 12m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$76
This JetBlue deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BDL
- ORD
1 stop6h 49m
JetBlue
Deal found 2/10![JetBlue logo]()
$77
Find flight deals from Massachusetts to Wisconsin
Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $134 (Super.com) |
One-way from | $67 (Super.com) |
Popular in | November |
Cheapest in | September |
Average price | $331 |
Good round-trip deal | $299 or less |
Good one-way deal | $228 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Wisconsin that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.
Fly from
Massachusetts
Fly to
Wisconsin
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/3
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 3/9
6:04 am-2:14 pm
1 stop7h 10m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/2
7:15 am-9:25 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 4/6
7:35 pm-11:02 pm
Nonstop2h 27m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/14
9:40 am-11:31 am
Nonstop2h 51m
Chicago O'Hare Intl
Fri 7/17
9:26 pm-12:59 am
Nonstop2h 33m
$145
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/11
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Sat 6/13
9:26 pm-12:59 am
Nonstop2h 33m
$145
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/26
7:15 am-9:28 am
Nonstop3h 13m
Chicago O'Hare Intl
Mon 3/2
7:05 am-10:37 am
Nonstop2h 32m
$147
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 4/5
7:25 am-9:35 am
Nonstop3h 10m
Chicago O'Hare Intl
Tue 4/7
10:40 am-2:04 pm
Nonstop2h 24m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/16
12:00 pm-1:54 pm
Nonstop2h 54m
Chicago O'Hare Intl
Tue 5/19
7:15 pm-10:49 pm
Nonstop2h 34m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 2/27
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 3/2
11:05 am-2:29 pm
Nonstop2h 24m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
5:45 am-9:37 am
1 stop4h 52m
Chicago O'Hare Intl
Tue 5/5
6:23 pm-9:59 pm
Nonstop2h 36m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/25
8:40 pm-10:35 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sat 5/30
4:30 pm-8:03 pm
Nonstop2h 33m
$157
Showing 1-10 of 60 results
Best time to book a flight from Massachusetts to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Massachusetts with our price prediction graph.
BOS-ORD
BDL-MSP
BOS-MSN
BDL-ORD
ALB-MSP
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 Massachusetts to Wisconsin
USMA-USWI
BOS-ORD
BDL-MSP
BOS-MSN
BDL-ORD
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in December is currently the most expensive (average of $254). 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.
What is the cheapest time of day to fly from MA to WI?
Find hourly flight availability from Massachusetts to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 51% versus a flight in the evening.
What is the cheapest day to fly from Massachusetts to Wisconsin?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Wisconsin. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Massachusetts 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 February 12, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Massachusetts 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 Massachusetts 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 Massachusetts to Wisconsin by cabin class
Find flights from Massachusetts to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Wisconsin flights
Browse other Massachusetts and Wisconsin flight options. Last updated on February 12, 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 Massachusetts after your stay in Wisconsin
Massachusetts to Wisconsin flights
Consider these flights traveling from Massachusetts to Wisconsin.
Top 5 airlines flying from Massachusetts to Wisconsin
Discover the top 5 airlines that operate flights from Massachusetts to Wisconsin. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$280 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$273 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$436 | FlexibilityNo cancel fee | On-time69% |