$70+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 12 — May 191
Round-trip
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 April 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 April 12, 2026.
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:25 am
BOS
- ORD
1 stop13h 14m
Multiple Airlines
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$145
This JetBlue deal was found by Cheapflights users on 4/8. 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 4/287:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Tue 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/8![JetBlue logo]()
$147
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/8![Frontier logo]()
$151
This Expedia deal was found by Cheapflights users on 4/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:16 pm
BOS
- ORD
1 stop14h 20m
Multiple Airlines
Tue 4/286:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 4/8. 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 5/1612:00 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 5/207:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/8![Delta logo]()
$153
This Priceline deal was found by Cheapflights users on 4/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Mon 5/44:28 pm
ORD
- BOS
1 stop8h 03m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 4/7. 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.
Wed 5/137:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Wed 5/137:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Deal found 4/7![Delta logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
BOS
- ORD
1 stop13h 39m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 4/8. 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.
Wed 5/1311:00 am
BOS
- ORD
1 stop8h 07m
Delta
Tue 5/197:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/8![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 4/8. 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 4/299:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Fri 5/17:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/8![United Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Tue 5/122:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 4/7![Southwest logo]()
$159
This Frontier deal was found by Cheapflights users on 4/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/8![Frontier logo]()
$160
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 April 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 April 12, 2026.
This United Airlines deal was found by Cheapflights users on 4/9. 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 6/56:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 6/912:53 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/9![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 4/9. 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 5/211:00 am
BOS
- MKE
Nonstop2h 47m
Delta
Mon 5/47:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/9![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 4/8. 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.
Wed 5/139:15 am
BOS
- ORD
2 stops10h 10m
Southwest
Sun 5/172:00 pm
ORD
- BOS
2 stops17h 05m
Southwest
Deal found 4/8![Southwest logo]()
$200
This Sun Country Air deal was found by Cheapflights users on 4/10. 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.
Fri 7/311:52 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 7/267:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 4/10![Sun Country Air logo]()
$264
This United Airlines deal was found by Cheapflights users on 4/11. 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 5/37:30 am
BOS
- ORD
Nonstop3h 01m
United Airlines
Wed 5/63:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/11![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Mon 4/275:09 pm
BOS
- ATW
2 stops7h 31m
American Airlines
Thu 4/306:31 pm
ATW
- BOS
1 stop4h 54m
American Airlines
Deal found 4/7![American Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Sun 5/109:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/179:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 4/9![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/7. 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 4/306:00 am
BOS
- MKE
1 stop5h 20m
Delta
Tue 5/57:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/7![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/9. 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.
Sun 5/105:15 am
BOS
- ORD
1 stop10h 45m
Southwest
Sun 5/172:00 pm
ORD
- BOS
2 stops17h 05m
Southwest
Deal found 4/9![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 4/7. 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.
Sat 5/29:25 am
BOS
- MKE
1 stop4h 49m
Delta
Wed 5/66:00 am
MKE
- BOS
1 stop5h 22m
Delta
Deal found 4/7![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Tue 6/99:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sat 9/59:30 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/7![United Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/289:58 am
ALB
- MSP
2 stops34h 53m
Multiple Airlines
Sat 7/47:10 am
MSP
- ALB
1 stop27h 20m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 4/11. 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.
Wed 7/15:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 7/69:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/11![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:35 am
BOS
- ORD
1 stop10h 25m
Southwest
Sat 4/1811:50 am
ORD
- BOS
2 stops10h 50m
Southwest
Deal found 4/7![Southwest logo]()
$250
This United Airlines deal was found by Cheapflights users on 4/11. 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 4/257:30 pm
BOS
- ORD
1 stop5h 13m
United Airlines
Tue 4/286:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/11![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/194:00 pm
BOS
- MKE
1 stop7h 17m
Delta
Tue 6/237:10 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 4/12![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 4/9. 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.
Sun 5/2410:10 am
BOS
- ORD
2 stops12h 45m
Southwest
Sun 5/312:00 pm
ORD
- BOS
2 stops17h 05m
Southwest
Deal found 4/9![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 4/7. 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 5/2212:55 pm
BOS
- ORD
Nonstop2h 53m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/7![Delta logo]()
$247
This American Airlines deal was found by Cheapflights users on 4/11. 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.
Fri 7/36:30 pm
BOS
- ATW
1 stop6h 01m
American Airlines
Tue 7/75:30 am
ATW
- BOS
2 stops7h 58m
American Airlines
Deal found 4/11![American Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 4/9. 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.
Tue 5/122:25 pm
BOS
- MKE
2 stops8h 20m
Southwest
Mon 5/183:50 pm
MKE
- BOS
2 stops7h 05m
Southwest
Deal found 4/9![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 4/7. 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.
Wed 5/205:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Mon 5/256:00 am
MKE
- BOS
1 stop7h 15m
Delta
Deal found 4/7![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 4/9. 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 5/86:39 pm
BOS
- MKE
1 stop4h 54m
United Airlines
Sun 5/105:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 4/9![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:25 am
BOS
- MKE
2 stops7h 25m
Southwest
Mon 5/118:00 am
MKE
- BOS
2 stops8h 10m
Southwest
Deal found 4/7![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 4/11. 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 5/97:30 am
BOS
- MKE
1 stop7h 57m
United Airlines
Tue 5/129:37 am
MKE
- BOS
1 stop4h 26m
United Airlines
Deal found 4/11![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/9. 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 5/215:40 am
BOS
- ATW
1 stop5h 48m
Delta
Fri 5/296:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 4/9![Delta logo]()
$307
This KAYAK deal was found by Cheapflights users on 4/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
BDL
- ORD
1 stop5h 46m
American Airlines
Tue 4/288:39 am
ORD
- BDL
1 stop5h 34m
American Airlines
Deal found 4/9![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 4/10. 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 5/197:05 am
BDL
- ORD
1 stop10h 00m
Southwest
Wed 5/201:35 pm
ORD
- BDL
1 stop8h 05m
Southwest
Deal found 4/10![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 4/11. 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.
Sat 5/232:16 pm
ALB
- ORD
1 stop7h 08m
Delta
Wed 5/275:30 am
ORD
- ALB
1 stop5h 25m
Delta
Deal found 4/11![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Sat 7/46:45 pm
BOS
- ATW
1 stop5h 15m
United Airlines
Sat 7/112:40 pm
ATW
- BOS
1 stop6h 16m
United Airlines
Deal found 4/9![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:05 am
BOS
- MSN
1 stop4h 49m
Delta
Sat 9/264:00 pm
MSN
- BOS
Nonstop2h 34m
Delta
Deal found 4/12![Delta logo]()
$323
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 12, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 12, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:16 pm
BOS
- ORD
1 stop14h 20m
Multiple Airlines
Tue 4/286:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$152
This Frontier deal was found by Cheapflights users on 4/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 4/7![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Wed 4/226:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 4/7![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 pm
BOS
- ORD
1 stop30h 59m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$161
This Delta deal was found by Cheapflights users on 4/7. 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.
Wed 4/224:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Wed 4/297:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 4/7![Delta logo]()
$163
This Delta deal was found by Cheapflights users on 4/7. 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.
Wed 4/225:30 pm
BOS
- ORD
1 stop7h 29m
Delta
Tue 4/287:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 4/7![Delta logo]()
$173
This Frontier deal was found by Cheapflights users on 4/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:00 am
BOS
- MKE
1 stop11h 28m
Frontier
Mon 5/1112:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/10![Frontier logo]()
$180
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Tue 5/59:56 am
MKE
- BOS
1 stop22h 16m
Frontier
Deal found 4/7![Frontier logo]()
$171
This Priceline deal was found by Cheapflights users on 4/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:25 pm
BOS
- MKE
Nonstop2h 36m
Multiple Airlines
Mon 5/46:23 pm
MKE
- BOS
1 stop6h 08m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$164
This KAYAK deal was found by Cheapflights users on 4/7. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:44 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Wed 5/64:58 pm
MKE
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/7![JetBlue logo]()
$165
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:16 am
BOS
- MKE
1 stop22h 22m
Multiple Airlines
Tue 5/54:56 pm
MKE
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$174
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
BOS
- MKE
1 stop6h 34m
Multiple Airlines
Tue 6/28:41 am
MKE
- BOS
Nonstop2h 19m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$169
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 April 12, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 12, 2026.
This Frontier deal was found by Cheapflights users on 4/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/8![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 4/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 4/8![Frontier logo]()
$75
This Expedia deal was found by Cheapflights users on 4/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Deal found 4/7![Frontier logo]()
$76
This Priceline deal was found by Cheapflights users on 4/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/8![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 4/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:28 pm
BOS
- ORD
1 stop11h 11m
Frontier
Deal found 4/9![Frontier logo]()
$77
This KAYAK deal was found by Cheapflights users on 4/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/10![JetBlue logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:52 am
ALB
- ORD
1 stop14h 07m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:35 am
BOS
- ORD
1 stop10h 25m
Southwest
Deal found 4/7![Southwest logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 4/8. 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.
Wed 4/228:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$81
This CheapOair deal was found by Cheapflights users on 4/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:53 am
BOS
- MKE
1 stop25h 33m
Frontier
Deal found 4/11![Frontier logo]()
$82
This KAYAK deal was found by Cheapflights users on 4/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/10![JetBlue logo]()
$82
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 April 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $145 (Expedia) |
One-way from | $70 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $443 |
Good round-trip deal | $153 or less |
Good one-way deal | $198 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 April 12, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/5
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 6/9
12:53 pm-4:29 pm
Nonstop2h 36m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/3
7:30 am-9:31 am
Nonstop3h 01m
Chicago O'Hare Intl
Wed 5/6
3:55 pm-7:26 pm
Nonstop2h 31m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/10
9:20 am-11:20 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/17
9:30 pm-12:59 am
Nonstop2h 29m
$177
Quickest round-trip
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Sat 5/2
11:00 am-12:47 pm
Nonstop2h 47m
Milwaukee-Mitchell
Mon 5/4
7:58 pm-11:21 pm
Nonstop2h 23m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/9
9:50 am-11:43 am
Nonstop2h 53m
Chicago O'Hare Intl
Sat 9/5
9:30 pm-1:05 am
Nonstop2h 35m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/1
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Mon 7/6
9:35 pm-1:08 am
Nonstop2h 33m
$196
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Thu 4/30
6:00 am-10:20 am
1 stop5h 20m
Milwaukee-Mitchell
Tue 5/5
7:58 pm-11:21 pm
Nonstop2h 23m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 4/25
7:30 pm-11:43 pm
1 stop5h 13m
Chicago O'Hare Intl
Tue 4/28
6:23 pm-9:59 pm
Nonstop2h 36m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/13
9:15 am-6:25 pm
2 stops10h 10m
Chicago O'Hare Intl
Sun 5/17
2:00 pm-8:05 am
2 stops17h 05m
$200
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Sat 5/2
9:25 am-1:14 pm
1 stop4h 49m
Milwaukee-Mitchell
Wed 5/6
6:00 am-12:22 pm
1 stop5h 22m
$207
Showing 1-10 of 60 resultsSorted by cheapest first
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
BOS-MKE
ALB-ORD
BDL-MSP
BOS-ATW
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
BOS-MKE
ALB-ORD
BDL-MSP
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 April 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 in the evening, which can drop the price by up to 38% versus a flight in the morning.
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 April 4, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings 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 April 12, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 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 April 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$269 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$268 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$430 | FlexibilityNo cancel fee | On-time71% |