$60+ Cheap flights from Wisconsin to Massachusetts
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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Wisconsin to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Wisconsin to MassachusettsExplore the most affordable flight options available from Wisconsin to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Wisconsin to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/89:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Thu 4/97:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 1/31![United Airlines logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Fri 4/37:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/2![United Airlines logo]()
$132
This Super.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/57:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Sun 2/83:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 2/1![JetBlue logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/67:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Sun 2/83:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 2/3![JetBlue logo]()
$134
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/1710:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Thu 2/197:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/64:30 pm
ORD
- BOS
Nonstop2h 14m
American Airlines
Sun 2/87:00 am
BOS
- ORD
Nonstop3h 05m
American Airlines
Deal found 2/2![American Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 4/67:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/1![United Airlines logo]()
$137
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/186:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Sun 2/227:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$139
This Priceline deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 4/710:00 am
ORD
- BOS
Nonstop2h 27m
Multiple Airlines
Tue 4/1412:55 pm
BOS
- ORD
1 stop10h 44m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Sat 3/76:45 pm
BOS
- ORD
1 stop5h 15m
JetBlue
Deal found 2/3![JetBlue logo]()
$141
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2512:59 pm
ORD
- BOS
1 stop5h 59m
JetBlue
Wed 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/1![JetBlue logo]()
$142
This Frontier deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:05 am
ORD
- BDL
1 stop7h 27m
Frontier
Mon 3/210:52 am
BDL
- ORD
1 stop13h 23m
Frontier
Deal found 2/2![Frontier logo]()
$148
Best flights from Wisconsin to MassachusettsDiscover carefully curated flight deals from Wisconsin to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Wisconsin to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/89:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Thu 4/97:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 1/31![United Airlines logo]()
$131
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/77:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Tue 2/103:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 2/1![JetBlue logo]()
$135
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/107:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Sun 4/127:25 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/1![Delta logo]()
$142
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Thu 2/265:05 am
ORD
- BDL
1 stop7h 27m
Frontier
Sun 3/19:10 pm
BDL
- ORD
1 stop27h 05m
Frontier
Deal found 2/2![Frontier logo]()
$189
This Sun Country Air deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Mon 6/157:06 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 2/2![Sun Country Air logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/129:15 am
ORD
- ALB
1 stop23h 47m
Multiple Airlines
Mon 3/1610:52 am
ALB
- ORD
1 stop24h 44m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$206
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/1410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Fri 2/207:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/1![JetBlue logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:31 pm
ATW
- BOS
1 stop4h 52m
American Airlines
Wed 4/296:00 am
BOS
- ATW
2 stops8h 00m
American Airlines
Deal found 2/2![American Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/267:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Mon 3/307:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 2/2![United Airlines logo]()
$142
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 4/86:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Sun 4/127:25 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/2![Delta logo]()
$142
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:30 pm
MKE
- BOS
1 stop5h 20m
Southwest
Sun 5/107:40 pm
BOS
- MKE
1 stop5h 15m
Southwest
Deal found 2/1![Southwest logo]()
$312
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Mon 3/26:28 pm
BOS
- ORD
Nonstop3h 02m
United Airlines
Deal found 2/1![United Airlines logo]()
$142
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/246:04 am
ORD
- BOS
1 stop7h 12m
JetBlue
Tue 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/1![JetBlue logo]()
$142
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/102:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
Thu 3/127:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/2![Delta logo]()
$147
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2512:59 pm
ORD
- BOS
1 stop5h 59m
JetBlue
Sat 2/287:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/1![JetBlue logo]()
$142
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:01 pm
ORD
- BOS
1 stop4h 58m
United Airlines
Wed 4/157:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 2/2![United Airlines logo]()
$147
This Sun Country Air deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 5/36:55 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Fri 5/811:39 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Deal found 2/1![Sun Country Air logo]()
$223
This Sun Country Air deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Wed 8/1211:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Deal found 2/2![Sun Country Air logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/114:18 pm
ORD
- ALB
1 stop25h 13m
Multiple Airlines
Mon 3/1610:52 am
ALB
- ORD
1 stop24h 44m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 4/285:00 am
ORD
- ALB
1 stop5h 02m
American Airlines
Wed 4/292:07 pm
ALB
- ORD
Nonstop2h 54m
American Airlines
Deal found 2/2![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:29 pm
MKE
- BOS
1 stop4h 47m
United Airlines
Sat 5/305:45 pm
BOS
- MKE
1 stop6h 42m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This Sun Country Air deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Mon 6/86:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Mon 6/1510:35 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Deal found 2/2![Sun Country Air logo]()
$248
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Tue 7/149:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Deal found 2/2![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:42 pm
ORD
- ALB
2 stops17h 18m
Multiple Airlines
Thu 2/197:23 pm
ALB
- ORD
1 stop23h 23m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2511:30 am
MKE
- BOS
1 stop4h 49m
United Airlines
Wed 3/117:16 am
BOS
- MKE
1 stop6h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/259:30 am
MKE
- BOS
2 stops12h 55m
Southwest
Fri 3/275:15 am
BOS
- MKE
1 stop5h 25m
Southwest
Deal found 2/2![Southwest logo]()
$323
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 5/158:44 pm
ORD
- ALB
Nonstop2h 15m
American Airlines
Mon 5/1811:57 am
ALB
- ORD
Nonstop2h 54m
American Airlines
Deal found 2/3![American Airlines logo]()
$309
This Sun Country Air deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Sat 5/25:50 am
MSP
- BOS
Nonstop2h 44m
Sun Country Air
Sun 5/1011:39 am
BOS
- MSP
Nonstop3h 10m
Sun Country Air
Deal found 2/1![Sun Country Air logo]()
$258
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/67:18 pm
MKE
- BOS
1 stop4h 17m
United Airlines
Mon 3/94:30 pm
BOS
- MKE
1 stop6h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/65:48 pm
MKE
- BDL
1 stop5h 06m
Delta
Wed 5/136:00 am
BDL
- MKE
1 stop6h 25m
Delta
Deal found 2/2![Delta logo]()
$263
Last-minute flights from Wisconsin to MassachusettsDiscover last-minute flight deals from Wisconsin to Massachusetts. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Massachusetts. Data last updated February 3, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/57:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Mon 2/93:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 2/1![JetBlue logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/67:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Sun 2/83:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 2/3![JetBlue logo]()
$134
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/64:30 pm
ORD
- BOS
Nonstop2h 14m
American Airlines
Sun 2/87:00 am
BOS
- ORD
Nonstop3h 05m
American Airlines
Deal found 2/2![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Fri 2/207:15 am
BOS
- ORD
Nonstop3h 13m
Delta
Deal found 2/1![Delta logo]()
$137
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/1710:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Thu 2/197:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$135
This Priceline deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/186:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Sun 2/227:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$139
This CheapOair deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/256:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Wed 3/115:27 am
BOS
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$140
This JetBlue deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2512:59 pm
ORD
- BOS
1 stop5h 59m
JetBlue
Tue 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/1![JetBlue logo]()
$142
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/2612:44 pm
ORD
- BOS
1 stop6h 14m
JetBlue
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/3![JetBlue logo]()
$143
This Frontier deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:05 am
ORD
- BDL
1 stop7h 27m
Frontier
Mon 3/210:52 am
BDL
- ORD
1 stop13h 23m
Frontier
Deal found 2/2![Frontier logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Sat 3/76:45 pm
BOS
- ORD
1 stop5h 15m
JetBlue
Deal found 2/3![JetBlue logo]()
$141
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Fri 4/37:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/2![United Airlines logo]()
$132
One-way flights from Wisconsin to MassachusettsSearch for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/48:30 am
ORD
- BDL
1 stop25h 07m
Frontier
Deal found 2/3![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/1210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/1![JetBlue logo]()
$67
This JetBlue deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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.
Fri 2/67:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 2/3![JetBlue logo]()
$68
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 2/3![Delta logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/412:44 pm
ORD
- BDL
1 stop20h 53m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$69
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$70
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
ORD
- BDL
1 stop25h 07m
Frontier
Deal found 2/3![Frontier logo]()
$70
This CheapOair deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:51 pm
ORD
- BOS
1 stop20h 04m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$71
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:51 pm
ORD
- BOS
2 stops15h 57m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$72
This Orbitz deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- BOS
1 stop9h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$73
This Super.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/248:30 am
ORD
- BDL
1 stop23h 53m
Frontier
Deal found 2/1![Frontier logo]()
$73
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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.
Mon 3/24:42 pm
ORD
- BOS
1 stop7h 31m
Frontier
Deal found 2/3![Frontier logo]()
$74
Find flight deals from Wisconsin to Massachusetts
Keep the following information in mind while searching for Wisconsin to Massachusetts flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (United Airlines) |
One-way from | $60 (Kiwi.com) |
Popular in | January |
Cheapest in | September |
Average price | $321 |
Good round-trip deal | $299 or less |
Good one-way deal | $238 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Massachusetts 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 3, 2026.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.
Fly from
Wisconsin
Fly to
Massachusetts
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/8
9:15 am-12:46 pm
Nonstop2h 31m
Boston Logan Intl
Thu 4/9
7:00 am-9:00 am
Nonstop3h 00m
$131
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/7
7:40 am-11:05 am
Nonstop2h 25m
Boston Logan Intl
Tue 2/10
3:35 pm-5:43 pm
Nonstop3h 08m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/14
10:00 am-1:20 pm
Nonstop2h 20m
Boston Logan Intl
Fri 2/20
7:00 am-9:10 am
Nonstop3h 10m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 4/10
7:35 pm-11:02 pm
Nonstop2h 27m
Boston Logan Intl
Sun 4/12
7:25 am-9:35 am
Nonstop3h 10m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 3/26
7:30 am-10:49 am
Nonstop2h 19m
Boston Logan Intl
Mon 3/30
7:15 am-9:14 am
Nonstop2h 59m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/8
6:15 am-9:40 am
Nonstop2h 25m
Boston Logan Intl
Sun 4/12
7:25 am-9:35 am
Nonstop3h 10m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 2/27
11:05 am-2:29 pm
Nonstop2h 24m
Boston Logan Intl
Mon 3/2
6:28 pm-8:30 pm
Nonstop3h 02m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 2/24
6:04 am-2:16 pm
1 stop7h 12m
Boston Logan Intl
Tue 3/3
7:00 am-9:10 am
Nonstop3h 10m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/25
12:59 pm-7:58 pm
1 stop5h 59m
Boston Logan Intl
Sat 2/28
7:00 am-9:10 am
Nonstop3h 10m
$142
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 3/10
2:10 pm-5:38 pm
Nonstop2h 28m
Boston Logan Intl
Thu 3/12
7:15 am-9:25 am
Nonstop3h 10m
$147
Showing 1-10 of 60 results
Best time to book a flight from Wisconsin to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Wisconsin with our price prediction graph.
ORD-BOS
ORD-BDL
MSP-BDL
MKE-BOS
MSN-BOS
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 Wisconsin to Massachusetts
USWI-USMA
ORD-BOS
ORD-BDL
MSP-BDL
MKE-BOS
What is the cheapest month to book a flight from Wisconsin to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $93). Flying from Wisconsin to Massachusetts in December is currently the most expensive (average of $217). 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 WI to MA?
Find hourly flight availability from Wisconsin to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 3, 2026.
A simple way to save on the total cost of your ticket is to fly from Wisconsin to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Wisconsin to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Massachusetts. Price data was last updated on January 31, 2026.
Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Wisconsin to Massachusetts
Explore weekly flight availability from Wisconsin to Massachusetts. 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 3, 2026.
The most flights from USWI to USMA 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 (4 on average).
How much does it cost to fly round-trip from Wisconsin to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated February 3, 2026.
Read through reviews of airlines operating flights from Wisconsin to Massachusetts, such as Southwest, Delta, and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Wisconsin to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Massachusetts by cabin class
Find flights from Wisconsin to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Massachusetts flights
Browse other Wisconsin and Massachusetts flight options. Last updated on February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Wisconsin after your stay in Massachusetts
Wisconsin to Massachusetts flights
Consider these flights traveling from Wisconsin to Massachusetts.
Top 5 airlines flying from Wisconsin to Massachusetts
Discover the top 5 airlines that operate flights from Wisconsin to Massachusetts. 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$271 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$260 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$402 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$383 | FlexibilityNo cancel fee | On-time69% |