$96+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Aug 22 — Aug 291
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 July 23, 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 July 23, 2026.
This FlightHub deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2611:15 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 8/26:55 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/18![Sun Country Air logo]()
$188
This Flysmarter deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Sun 9/136:20 am
ORD
- BOS
1 stop6h 24m
JetBlue
Deal found 7/21![JetBlue logo]()
$188
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Sat 8/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/19![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This SmartFares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 8/126:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/20![JetBlue logo]()
$194
This SmartFares deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Wed 9/231:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/21![JetBlue logo]()
$195
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/211:29 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Thu 8/68:05 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/21![Sun Country Air logo]()
$196
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Tue 10/208:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/19![JetBlue logo]()
$197
This Sun Country Air deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 7/2611:15 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Mon 7/276:45 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/18![Sun Country Air logo]()
$198
This Flysmarter deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/20![JetBlue logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Sat 9/1211:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Deal found 7/19![JetBlue logo]()
$205
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 July 23, 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 July 23, 2026.
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Wed 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/21![JetBlue logo]()
$211
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Wed 9/237:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/23![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:27 pm
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 8/236:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 7/21![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:25 am
BOS
- MKE
2 stops6h 40m
Southwest
Tue 9/296:40 am
MKE
- BOS
1 stop4h 35m
Southwest
Deal found 7/19![Southwest logo]()
$232
This Sun Country Air deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:56 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Tue 8/116:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 7/23![Sun Country Air logo]()
$328
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:26 pm
ALB
- MSP
1 stop5h 26m
American Airlines
Mon 10/55:30 am
MSP
- ALB
1 stop5h 06m
American Airlines
Deal found 7/19![American Airlines logo]()
$381
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:09 pm
BOS
- ORD
1 stop6h 49m
JetBlue
Sat 9/1210:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Deal found 7/22![JetBlue logo]()
$221
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Sun 8/307:30 pm
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 7/20![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:36 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 9/277:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/23![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:30 am
BOS
- MKE
1 stop4h 35m
Southwest
Wed 8/266:40 am
MKE
- BOS
2 stops8h 20m
Southwest
Deal found 7/21![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:40 pm
BOS
- ORD
Nonstop2h 48m
Delta
Mon 10/267:30 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 7/19![Delta logo]()
$225
This JetBlue deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Fri 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/19![JetBlue logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 10/49:24 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Deal found 7/19![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Tue 8/1810:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 7/19![Delta logo]()
$225
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Sat 10/310:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Deal found 7/22![JetBlue logo]()
$227
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 am
BOS
- MKE
2 stops6h 35m
Southwest
Mon 9/144:50 pm
MKE
- BOS
1 stop4h 40m
Southwest
Deal found 7/22![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 9/93:05 pm
ORD
- BOS
Nonstop2h 47m
Delta
Deal found 7/23![Delta logo]()
$226
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/22![JetBlue logo]()
$228
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:54 pm
BOS
- MKE
1 stop5h 43m
United Airlines
Sun 8/235:00 am
MKE
- BOS
1 stop4h 54m
United Airlines
Deal found 7/19![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Fri 8/288:00 am
MKE
- BOS
2 stops8h 50m
Southwest
Deal found 7/19![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 9/1212:15 pm
BOS
- MKE
Nonstop2h 35m
Delta
Mon 9/146:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Deal found 7/18![Delta logo]()
$243
This Sun Country Air deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:33 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Fri 8/215:50 am
MSP
- BOS
Nonstop2h 48m
Sun Country Air
Deal found 7/23![Sun Country Air logo]()
$378
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:33 am
BDL
- ORD
1 stop7h 26m
United Airlines
Mon 9/76:15 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 7/23![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:50 am
BOS
- MKE
2 stops10h 05m
Southwest
Mon 8/174:50 pm
MKE
- BOS
1 stop4h 40m
Southwest
Deal found 7/20![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Fri 8/286:15 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 7/23![United Airlines logo]()
$300
This JetBlue deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Sun 9/133:00 pm
ORD
- BDL
1 stop7h 14m
JetBlue
Deal found 7/19![JetBlue logo]()
$308
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:35 pm
BOS
- MSP
2 stops9h 15m
Southwest
Mon 10/52:55 pm
MSP
- BOS
1 stop5h 25m
Southwest
Deal found 7/20![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:50 am
BDL
- MSP
Nonstop2h 51m
Delta
Mon 8/317:50 pm
MSP
- BDL
Nonstop2h 35m
Delta
Deal found 7/18![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
BDL
- ORD
1 stop4h 38m
United Airlines
Sun 9/66:19 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 7/18![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:25 pm
BDL
- MSP
1 stop4h 40m
Southwest
Sat 10/177:10 am
MSP
- BDL
1 stop7h 15m
Southwest
Deal found 7/22![Southwest logo]()
$327
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated July 23, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2611:15 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 8/26:55 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/18![Sun Country Air logo]()
$188
This Sun Country Air deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 7/2611:15 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Mon 7/276:45 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/18![Sun Country Air logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Tue 8/49:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/18![JetBlue logo]()
$225
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/211:29 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Thu 8/68:05 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/21![Sun Country Air logo]()
$196
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/27:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 8/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/19![United Airlines logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 8/86:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 7/19![United Airlines logo]()
$235
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/20![JetBlue logo]()
$217
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Tue 8/259:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/19![JetBlue logo]()
$205
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
BOS
- MKE
1 stop6h 36m
Delta
Tue 8/256:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/23![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Tue 8/258:20 am
MKE
- BOS
2 stops7h 45m
Southwest
Deal found 7/19![Southwest logo]()
$232
This Priceline deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/21![JetBlue logo]()
$207
This CheapOair deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/227:10 am
BOS
- MKE
Nonstop2h 34m
Multiple Airlines
Thu 8/2712:10 pm
MKE
- BOS
1 stop19h 59m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$234
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 July 23, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/19![JetBlue logo]()
$96
This Traveloka deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Deal found 7/18![JetBlue logo]()
$97
This Super.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:01 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 7/19![Sun Country Air logo]()
$98
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$98
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$99
This Flysmarter deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Deal found 7/18![JetBlue logo]()
$100
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/22![JetBlue logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/18![JetBlue logo]()
$102
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/22![JetBlue logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:11 pm
BOS
- ORD
1 stop6h 55m
JetBlue
Deal found 7/19![JetBlue logo]()
$104
This JetBlue deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 10/156:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/18![JetBlue logo]()
$106
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$109
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 July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Flysmarter) |
One-way from | $96 (Super.com) |
Popular in | November |
Cheapest in | July |
Average price | $272 |
Good round-trip deal | $227 or less |
Good one-way deal | $132 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 July 23, 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
Tue 8/11
2:45 pm-9:58 pm
1 stop8h 13m
Chicago O'Hare Intl
Wed 8/12
9:35 am-5:17 pm
1 stop6h 42m
$211
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/9
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 9/23
7:30 pm-11:09 pm
Nonstop2h 39m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/5
4:09 pm-9:58 pm
1 stop6h 49m
Chicago O'Hare Intl
Sat 9/12
10:59 am-5:21 pm
1 stop5h 22m
$221
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/21
12:27 pm-2:20 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 8/23
6:15 am-9:36 am
Nonstop2h 21m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/28
12:25 pm-2:19 pm
Nonstop2h 54m
Chicago O'Hare Intl
Sun 8/30
7:30 pm-11:02 pm
Nonstop2h 32m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 10/23
7:40 pm-9:28 pm
Nonstop2h 48m
Chicago O'Hare Intl
Mon 10/26
7:30 am-11:06 am
Nonstop2h 36m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/5
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Fri 8/7
8:20 pm-11:51 pm
Nonstop2h 31m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/12
8:50 pm-10:44 pm
Nonstop2h 54m
Chicago O'Hare Intl
Tue 8/18
10:30 am-1:59 pm
Nonstop2h 29m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/3
12:25 pm-2:19 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 9/9
3:05 pm-6:52 pm
Nonstop2h 47m
$226
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/24
10:36 am-12:29 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:04 am
Nonstop2h 34m
$227
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.
BDL-MSP
BOS-MKE
BOS-ORD
BOS-MSP
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
BDL-MSP
BOS-MKE
BOS-ORD
BOS-MSP
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $314). Flying from Massachusetts to Wisconsin in April is currently the most expensive (average of $452). 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 July 23, 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 21% versus a flight in the afternoon.
Weekly flight availability from Massachusetts to Wisconsin
Explore weekly flight availability from Massachusetts to Wisconsin. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 23, 2026.
The most flights from USMA to USWI are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Massachusetts to Wisconsin?
Airfare is below average for this route at the moment.
Massachusetts to Wisconsin flights typically cost between $210 and $394 in September.The cheapest round-trip price found within the last 5 days was $205 on JetBlue (Sep 9-Sep 12).
How far ahead should I book a flight from Massachusetts to Wisconsin?
Booking 53 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Wisconsin. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 July 18, 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. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated July 23, 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
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 July 23, 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$251 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$420 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$467 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$290 | FlexibilityNo cancel fee | On-time63% |