$89+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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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 July 6, 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 July 6, 2026.
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Tue 8/119:40 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Tue 8/185:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/2![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Sat 9/1210:30 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Deal found 7/1![American Airlines logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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.
Sat 9/51:49 pm
ORD
- BOS
Nonstop3h 10m
JetBlue
Fri 9/115:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/3![JetBlue logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 8/248:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 7/1![JetBlue logo]()
$175
This JetBlue deal was found by Cheapflights users on 7/3. 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.
Sat 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/3![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Thu 7/236:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Wed 7/297:00 am
BOS
- ORD
Nonstop3h 01m
American Airlines
Deal found 7/3![American Airlines logo]()
$179
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 8/136:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Mon 8/178:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/1![United Airlines logo]()
$180
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 9/96:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/2![JetBlue logo]()
$181
This Delta deal was found by Cheapflights users on 7/1. 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 9/47:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Sat 9/51:30 pm
BOS
- ORD
Nonstop2h 53m
Delta
Deal found 7/1![Delta logo]()
$182
This SmartFares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Sat 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$182
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/2![JetBlue logo]()
$183
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 July 6, 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 July 6, 2026.
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/56:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Tue 8/115:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/4![United Airlines logo]()
$172
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/56:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Wed 8/128:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 7/5![JetBlue logo]()
$175
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/154:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Wed 8/264:20 pm
BOS
- MKE
Nonstop2h 52m
Delta
Deal found 7/2![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/1. 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.
Sat 8/296:00 am
MSP
- ALB
1 stop7h 45m
Southwest
Tue 9/112:15 pm
ALB
- MSP
1 stop6h 50m
Southwest
Deal found 7/1![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/2. 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 8/136:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Sun 8/167:05 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/2![United Airlines logo]()
$180
This JetBlue deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/1911:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Wed 9/238:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/4![JetBlue logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/297:45 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Wed 9/25:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/4![United Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:00 am
ORD
- ACK
1 stop7h 40m
American Airlines
Wed 7/1511:19 am
ACK
- ORD
1 stop4h 51m
American Airlines
Deal found 7/5![American Airlines logo]()
$413
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:00 pm
ORD
- BOS
1 stop5h 51m
JetBlue
Mon 11/97:05 am
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/2![JetBlue logo]()
$201
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 8/2611:31 am
MKE
- BOS
Nonstop2h 28m
Delta
Fri 8/284:20 pm
BOS
- MKE
Nonstop2h 52m
Delta
Deal found 7/3![Delta logo]()
$232
This JetBlue deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/186:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 8/252:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/4![JetBlue logo]()
$201
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:24 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Tue 10/135:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/3![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/186:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Sat 7/257:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 7/5![Delta logo]()
$239
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Tue 9/158:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/2![JetBlue logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/317:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Sun 11/16:00 am
BOS
- ORD
1 stop4h 45m
United Airlines
Deal found 7/5![United Airlines logo]()
$216
This JetBlue deal was found by Cheapflights users on 7/1. 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 9/18:20 pm
ORD
- BOS
Nonstop2h 56m
JetBlue
Thu 9/106:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/1![JetBlue logo]()
$215
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 9/187:10 am
MSP
- BOS
1 stop8h 00m
Southwest
Mon 9/215:30 pm
BOS
- MSP
1 stop5h 35m
Southwest
Deal found 7/2![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Sat 7/256:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/1![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/256:59 am
ORD
- ACK
2 stops7h 58m
Delta
Sat 9/53:24 pm
ACK
- ORD
1 stop7h 28m
Delta
Deal found 7/5![Delta logo]()
$288
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 9/75:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
Deal found 7/2![JetBlue logo]()
$229
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/136:47 pm
MKE
- BOS
1 stop5h 23m
United Airlines
Sun 9/206:00 am
BOS
- MKE
1 stop5h 00m
United Airlines
Deal found 7/4![United Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 7/2. 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.
Mon 8/37:50 pm
MSP
- BDL
Nonstop2h 35m
Delta
Sun 8/96:50 am
BDL
- MSP
Nonstop2h 51m
Delta
Deal found 7/2![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 10/45:05 am
MSP
- BOS
2 stops8h 05m
Southwest
Wed 10/74:15 pm
BOS
- MSP
1 stop7h 30m
Southwest
Deal found 7/4![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 7/2. 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 8/47:50 pm
MSP
- BDL
Nonstop2h 35m
Delta
Mon 8/106:50 am
BDL
- MSP
Nonstop2h 51m
Delta
Deal found 7/2![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/47:50 pm
MSP
- BDL
Nonstop2h 35m
Delta
Mon 9/76:50 am
BDL
- MSP
Nonstop2h 51m
Delta
Deal found 7/5![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/1910:35 am
MSP
- ALB
1 stop4h 00m
Southwest
Tue 8/2512:50 pm
ALB
- MSP
1 stop6h 50m
Southwest
Deal found 7/5![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/196:47 pm
MKE
- BOS
1 stop5h 07m
United Airlines
Wed 9/235:45 am
BOS
- MKE
2 stops9h 48m
United Airlines
Deal found 7/5![United Airlines logo]()
$282
This JetBlue deal was found by Cheapflights users on 7/3. 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 8/146:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Mon 8/173:33 pm
ACK
- ORD
1 stop4h 54m
JetBlue
Deal found 7/3![JetBlue logo]()
$291
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/217:50 pm
MSP
- BDL
Nonstop2h 35m
Delta
Sun 8/236:50 am
BDL
- MSP
Nonstop2h 51m
Delta
Deal found 7/5![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/223:05 pm
MSP
- ALB
1 stop4h 45m
Southwest
Sat 8/297:25 am
ALB
- MSP
2 stops9h 45m
Southwest
Deal found 7/5![Southwest logo]()
$412
Last-minute flights from Wisconsin to MassachusettsDiscover last-minute flight deals from Wisconsin to Massachusetts. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Massachusetts. Data last updated July 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Thu 7/236:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Wed 7/297:00 am
BOS
- ORD
Nonstop3h 01m
American Airlines
Deal found 7/3![American Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 8/228:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 7/6![JetBlue logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 11/95:00 pm
BOS
- ORD
Nonstop3h 12m
JetBlue
Deal found 7/2![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/1112:52 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Thu 8/135:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/5![United Airlines logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 8/136:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Mon 8/178:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/1![United Airlines logo]()
$180
This JetBlue deal was found by Cheapflights users on 7/3. 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.
Sat 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/3![JetBlue logo]()
$176
This SmartFares deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/1811:01 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Tue 8/255:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 7/4![JetBlue logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 8/248:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 7/1![JetBlue logo]()
$175
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 9/96:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/2![JetBlue logo]()
$181
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Sat 9/1210:30 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Deal found 7/1![American Airlines logo]()
$173
This SmartFares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Sat 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$182
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 July 6, 2026.
Search for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Sun Country Air deal was found by Cheapflights users on 7/2. 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.
Sun 8/26:55 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 7/2![Sun Country Air logo]()
$89
This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/1![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/2![JetBlue logo]()
$95
This JetBlue deal was found by Cheapflights users on 7/3. 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.
Mon 8/319:35 am
ORD
- ACK
1 stop4h 49m
JetBlue
Deal found 7/3![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 7/186:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/2![United Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/2![JetBlue logo]()
$97
This eDestinos deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:20 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 7/4![Sun Country Air logo]()
$97
This Super.com deal was found by Cheapflights users on 7/1. 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.
Sat 9/2611:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Deal found 7/1![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/2![JetBlue logo]()
$98
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/41:15 pm
MKE
- BOS
1 stop6h 45m
American Airlines
Deal found 7/4![American Airlines logo]()
$98
This Super.com deal was found by Cheapflights users on 7/1. 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.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/1![JetBlue logo]()
$99
This Sun Country Air deal was found by Cheapflights users on 7/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/127:20 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 7/3![Sun Country Air logo]()
$99
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 July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (United Airlines) |
One-way from | $89 (Sun Country Air) |
Popular in | February |
Cheapest in | May |
Average price | $304 |
Good round-trip deal | $217 or less |
Good one-way deal | $128 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 July 6, 2026.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/5
6:20 pm-9:56 pm
Nonstop2h 36m
Boston Logan Intl
Tue 8/11
5:45 am-9:38 am
1 stop4h 53m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/5
6:00 am-2:22 pm
1 stop7h 22m
Boston Logan Intl
Wed 8/12
8:15 am-10:11 am
Nonstop2h 56m
$175
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/13
6:00 am-11:17 am
1 stop4h 17m
Boston Logan Intl
Sun 8/16
7:05 am-9:03 am
Nonstop2h 58m
$180
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/29
7:45 am-11:19 am
Nonstop2h 34m
Boston Logan Intl
Wed 9/2
5:45 am-9:38 am
1 stop4h 53m
$182
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 9/19
11:25 am-3:04 pm
Nonstop2h 39m
Boston Logan Intl
Wed 9/23
8:45 am-10:35 am
Nonstop2h 50m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 11/6
1:00 pm-7:51 pm
1 stop5h 51m
Boston Logan Intl
Mon 11/9
7:05 am-11:56 am
1 stop5h 51m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/18
6:00 am-2:43 pm
1 stop7h 43m
Boston Logan Intl
Tue 8/25
2:45 pm-9:58 pm
1 stop8h 13m
$201
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 8/15
4:47 pm-11:59 pm
1 stop6h 12m
Boston Logan Intl
Wed 8/26
4:20 pm-6:12 pm
Nonstop2h 52m
$207
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 9/11
11:25 am-3:04 pm
Nonstop2h 39m
Boston Logan Intl
Tue 9/15
8:45 am-10:35 am
Nonstop2h 50m
$207
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/1
8:20 pm-12:16 am
Nonstop2h 56m
Boston Logan Intl
Thu 9/10
6:55 am-8:46 am
Nonstop2h 51m
$215
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MSP-BDL
ORD-BOS
ORD-ACK
MKE-BOS
MSP-ALB
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
MSP-BDL
ORD-BOS
ORD-ACK
MKE-BOS
What is the cheapest month to book a flight from Wisconsin to Massachusetts?
Currently, April is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $65). Flying from Wisconsin to Massachusetts in March is currently the most expensive (average of $197). 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 July 6, 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 39% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Wisconsin to Massachusetts?
How far ahead should I book a flight from Wisconsin to Massachusetts?
The best time to book flights from Wisconsin to Massachusetts is 82 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 July 4, 2026.
Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Tuesday at noon 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.
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 July 6, 2026.
Read through reviews of airlines operating flights from Wisconsin to Massachusetts, such as Southwest,Delta, andUnited 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
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
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 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 July 6, 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 July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$168 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$297 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$399 | FlexibilityNo cancel fee | On-time71% |