$66+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Mar 24 — Mar 311
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 22, 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 22, 2026.
This Priceline deal was found by Cheapflights users on 2/21. 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.
Tue 4/145:45 am
BOS
- ORD
1 stop12h 30m
Multiple Airlines
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 4/67:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 4/69:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/19![United Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/115:31 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 2/19![American Airlines logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Thu 5/79:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/117:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 2/21![United Airlines logo]()
$132
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/117:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Thu 3/269:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/19![United Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/20![Delta logo]()
$137
This Expedia deal was found by Cheapflights users on 2/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares 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 2/20![JetBlue logo]()
$140
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Fri 6/56:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Fri 6/59:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/18![United Airlines logo]()
$141
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 2/20![American Airlines logo]()
$142
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Sun 4/56:26 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 2/19![American Airlines logo]()
$143
This Priceline deal was found by Cheapflights users on 2/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
BOS
- MKE
1 stop11h 13m
Frontier
Mon 5/115:08 pm
MKE
- BOS
1 stop6h 43m
Frontier
Deal found 2/18![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 February 22, 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 22, 2026.
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 5/57:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Fri 5/87:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
Deal found 2/18![Delta logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Tue 5/265:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 2/18![United Airlines logo]()
$152
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:22 am
BDL
- MKE
1 stop8h 20m
Frontier
Wed 3/116:35 pm
MKE
- BDL
1 stop23h 38m
Frontier
Deal found 2/19![Frontier logo]()
$257
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 4/97:40 pm
BOS
- ATW
1 stop5h 00m
American Airlines
Wed 4/156:31 pm
ATW
- BOS
1 stop4h 54m
American Airlines
Deal found 2/19![American Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Fri 5/297:00 pm
BOS
- ORD
1 stop5h 30m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 2/18![United Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 2/18. 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.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/18![Delta logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:38 pm
ALB
- ORD
2 stops18h 42m
Multiple Airlines
Mon 5/255:05 am
ORD
- ALB
1 stop12h 58m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/66:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/94:20 pm
ORD
- BOS
Nonstop2h 22m
United Airlines
Deal found 2/19![United Airlines logo]()
$157
This Sun Country Air deal was found by Cheapflights users on 2/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:17 am
BOS
- MSP
Nonstop3h 16m
Sun Country Air
Sat 4/187:15 pm
MSP
- BOS
Nonstop2h 45m
Sun Country Air
Deal found 2/19![Sun Country Air logo]()
$359
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sun 5/35:50 pm
ALB
- MSP
1 stop5h 50m
Southwest
Thu 5/74:15 pm
MSP
- ALB
1 stop6h 00m
Southwest
Deal found 2/19![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 8/117:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Sat 8/156:50 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 2/18![Delta logo]()
$171
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/109:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/20![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 3/117:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Fri 3/137:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/18![Delta logo]()
$172
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 3/147:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Tue 3/1712:03 pm
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 2/21![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/108:20 pm
BOS
- ORD
Nonstop2h 56m
Delta
Fri 3/137:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/18![Delta logo]()
$181
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:03 am
BOS
- ATW
1 stop5h 57m
American Airlines
Mon 5/46:31 pm
ATW
- BOS
1 stop4h 52m
American Airlines
Deal found 2/20![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/15:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Mon 4/69:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/19![United Airlines logo]()
$184
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 3/129:55 am
BOS
- MKE
Nonstop2h 49m
Delta
Mon 3/167:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/19![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 3/184:50 pm
BOS
- MKE
Nonstop2h 50m
Delta
Wed 3/257:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/18![Delta logo]()
$207
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/184:26 pm
ALB
- MSP
1 stop7h 58m
American Airlines
Fri 3/206:03 pm
MSP
- ALB
1 stop4h 47m
American Airlines
Deal found 2/19![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/18. 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.
Thu 3/194:50 pm
BOS
- MKE
Nonstop2h 50m
Delta
Mon 3/237:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/18![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/116:00 am
BOS
- MKE
1 stop5h 08m
United Airlines
Tue 3/241:25 pm
MKE
- BOS
1 stop5h 17m
United Airlines
Deal found 2/19![United Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:40 pm
ALB
- MSP
1 stop4h 55m
Southwest
Mon 4/132:25 pm
MSP
- ALB
2 stops7h 50m
Southwest
Deal found 2/18![Southwest logo]()
$377
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:21 pm
ALB
- MSP
1 stop5h 38m
American Airlines
Mon 4/133:51 pm
MSP
- ALB
1 stop5h 34m
American Airlines
Deal found 2/18![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:00 am
BOS
- MKE
1 stop5h 30m
United Airlines
Tue 3/1011:00 am
MKE
- BOS
1 stop5h 19m
United Airlines
Deal found 2/20![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:30 am
BOS
- MKE
1 stop4h 20m
Delta
Mon 3/237:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/21![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:53 am
BDL
- MKE
1 stop5h 48m
American Airlines
Sun 3/295:00 am
MKE
- BDL
1 stop4h 10m
American Airlines
Deal found 2/18![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 2/18. 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 5/85:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Mon 5/115:01 pm
MKE
- BOS
1 stop5h 28m
Delta
Deal found 2/18![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/197:15 pm
BDL
- MKE
1 stop5h 09m
American Airlines
Sun 3/225:00 am
MKE
- BDL
1 stop4h 10m
American Airlines
Deal found 2/19![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:40 am
BOS
- MKE
1 stop4h 09m
Delta
Mon 5/116:43 pm
MKE
- BOS
1 stop3h 46m
Delta
Deal found 2/21![Delta logo]()
$227
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated February 22, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated February 22, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 2/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 2/2510:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/21![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 2/256:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Thu 3/269:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/19![United Airlines logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares 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
Tue 3/310:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/20![JetBlue logo]()
$140
This JetBlue deal was found by Cheapflights users on 2/21. 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.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/21![JetBlue logo]()
$145
This Expedia deal was found by Cheapflights users on 2/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Wed 4/15:05 am
ORD
- BOS
1 stop9h 23m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 3/17:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 2/22![United Airlines logo]()
$149
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:35 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Sun 3/86:00 am
ORD
- BOS
1 stop5h 56m
United Airlines
Deal found 2/22![United Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/115:31 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 2/19![American Airlines logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/117:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Thu 3/269:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/19![United Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/128:15 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Wed 3/187:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 2/19![United Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 2/19. 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.
Sat 3/215:35 pm
BOS
- ORD
Nonstop3h 08m
Delta
Tue 3/247:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/19![Delta logo]()
$152
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Tue 3/316:25 pm
BOS
- ORD
1 stop6h 12m
United Airlines
Sat 4/49:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/21![United Airlines logo]()
$139
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 22, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 22, 2026.
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 3/147:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Deal found 2/21![United Airlines logo]()
$66
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/20![JetBlue logo]()
$68
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:07 pm
BOS
- ORD
1 stop5h 54m
United Airlines
Deal found 2/20![United Airlines logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 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 2/20![Spirit Airlines logo]()
$70
This Spirit deal was found by Cheapflights users on 2/22. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 2/22![Spirit Airlines logo]()
$71
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 2/266:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Deal found 2/19![American Airlines logo]()
$72
This JetBlue deal was found by Cheapflights users on 2/20. 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 2/257:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/20![JetBlue logo]()
$73
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/214:54 pm
ALB
- ORD
Nonstop2h 41m
United Airlines
Deal found 2/22![United Airlines logo]()
$76
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Mon 4/67:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/21![United Airlines logo]()
$76
This JetBlue deal was found by Cheapflights users on 2/20. 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 3/186:00 am
BDL
- ORD
1 stop6h 25m
JetBlue
Deal found 2/20![JetBlue logo]()
$77
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1012:07 pm
BOS
- ORD
1 stop5h 54m
United Airlines
Deal found 2/22![United Airlines logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:50 pm
BDL
- ORD
1 stop28h 04m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$79
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $129 (Priceline) |
One-way from | $66 (United Airlines) |
Popular in | November |
Cheapest in | September |
Average price | $354 |
Good round-trip deal | $388 or less |
Good one-way deal | $158 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 22, 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 5/5
7:35 pm-9:29 pm
Nonstop2h 54m
Chicago O'Hare Intl
Fri 5/8
7:15 pm-10:49 pm
Nonstop2h 34m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/26
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sun 5/31
6:15 am-9:39 am
Nonstop2h 24m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
7:00 pm-11:30 pm
1 stop5h 30m
Chicago O'Hare Intl
Sun 5/31
6:15 am-9:39 am
Nonstop2h 24m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/2
7:15 am-9:25 am
Nonstop3h 10m
Chicago O'Hare Intl
Sun 4/5
6:15 am-9:40 am
Nonstop2h 25m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 3/6
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 3/9
4:20 pm-7:42 pm
Nonstop2h 22m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/8
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/10
9:30 pm-12:59 am
Nonstop2h 29m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/11
7:00 am-8:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 8/15
6:50 pm-10:27 pm
Nonstop2h 37m
$171
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/11
7:15 am-9:25 am
Nonstop3h 10m
Chicago O'Hare Intl
Fri 3/13
7:00 am-10:25 am
Nonstop2h 25m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 3/14
7:16 am-9:22 am
Nonstop3h 06m
Chicago O'Hare Intl
Tue 3/17
12:03 pm-5:19 pm
1 stop4h 16m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/10
8:20 pm-10:16 pm
Nonstop2h 56m
Chicago O'Hare Intl
Fri 3/13
7:00 am-10:25 am
Nonstop2h 25m
$181
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
ALB-ORD
BDL-ORD
BDL-MSP
BDL-MKE
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
ALB-ORD
BDL-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 February 22, 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 50% 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 21, 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.
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 February 22, 2026.
The most flights from USMA to USWI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
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 22, 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.
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
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
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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 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$281 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$274 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$218 | Average$439 | FlexibilityNo cancel fee | On-time69% |