$64+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Mar 31 — Apr 71
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 March 1, 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 March 1, 2026.
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:00 am
BOS
- ORD
1 stop7h 30m
Southwest
Mon 5/112:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 2/27![Southwest logo]()
$128
This Priceline deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Thu 4/164:28 pm
ORD
- BOS
1 stop8h 03m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Sat 4/188:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 2/25![American Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:00 am
BOS
- ORD
Nonstop2h 52m
Delta
Wed 9/910:10 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 2/27![Delta logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 5/207:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/259:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/24![United Airlines logo]()
$132
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/16:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/47:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 2/25![United Airlines logo]()
$133
This Expedia deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/174:25 pm
BOS
- ORD
Nonstop3h 06m
Delta
Tue 3/247:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/26![Delta logo]()
$136
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 2/27![Delta logo]()
$137
This Priceline deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/86:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$139
This Booking.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2411:04 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 8/27:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 2/26![Sun Country Air logo]()
$178
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 8/259:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Wed 9/27:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Deal found 2/28![Delta logo]()
$187
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 March 1, 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 March 1, 2026.
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 8/267:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 2/28![Delta logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/297:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 4/57:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 2/28![United Airlines logo]()
$142
This JetBlue deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Thu 4/168:31 am
ORD
- BOS
1 stop4h 47m
JetBlue
Deal found 2/27![JetBlue logo]()
$171
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:20 am
BOS
- ORD
2 stops10h 45m
Southwest
Fri 5/12:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 2/28![Southwest logo]()
$182
This Sun Country Air deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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.
Wed 7/2911:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Sun 8/25:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 2/24![Sun Country Air logo]()
$279
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/117:16 pm
BOS
- GRB
1 stop5h 16m
American Airlines
Wed 3/185:00 am
GRB
- BOS
1 stop4h 46m
American Airlines
Deal found 2/28![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 2/25![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 4/38:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Wed 4/158:45 am
ORD
- BOS
1 stop4h 57m
United Airlines
Deal found 2/26![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/75:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Mon 5/113:30 pm
MKE
- BOS
1 stop5h 20m
Southwest
Deal found 2/28![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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
Mon 3/237:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/25![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 6/216:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/2412:11 pm
ORD
- BOS
1 stop4h 46m
United Airlines
Deal found 2/27![United Airlines logo]()
$213
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/189:00 pm
BOS
- ORD
Nonstop2h 55m
Delta
Tue 4/217:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 2/27![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/25:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/24![United Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/28:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Thu 4/94:20 pm
ORD
- BOS
1 stop6h 39m
United Airlines
Deal found 2/28![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/248:20 pm
BOS
- ORD
Nonstop2h 56m
Delta
Sun 3/297:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/27![Delta logo]()
$222
This Sun Country Air deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 7/1911:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Tue 7/286:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 2/27![Sun Country Air logo]()
$304
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/236:23 pm
BOS
- MKE
1 stop5h 20m
United Airlines
Wed 3/2511:00 am
MKE
- BOS
1 stop5h 19m
United Airlines
Deal found 2/26![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 7/48:00 pm
ALB
- ORD
Nonstop2h 45m
American Airlines
Wed 7/86:00 am
ORD
- ALB
1 stop4h 35m
American Airlines
Deal found 2/28![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/245:55 am
BDL
- MKE
1 stop6h 40m
Southwest
Tue 3/244:10 pm
MKE
- BDL
2 stops5h 45m
Southwest
Deal found 2/27![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/145:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Mon 5/187:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 2/25![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 4/95:30 am
BOS
- ATW
1 stop6h 02m
Delta
Wed 4/1512:05 pm
ATW
- BOS
1 stop6h 30m
Delta
Deal found 2/27![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:50 am
BDL
- ORD
2 stops10h 40m
Southwest
Mon 5/112:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Deal found 2/27![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/273:10 pm
BOS
- GRB
1 stop7h 52m
Delta
Fri 4/35:17 pm
GRB
- BOS
1 stop5h 36m
Delta
Deal found 2/25![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/276:00 am
BOS
- GRB
1 stop4h 59m
United Airlines
Fri 4/31:30 pm
GRB
- BOS
2 stops7h 24m
United Airlines
Deal found 2/27![United Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 7/35:40 am
BOS
- ATW
1 stop6h 31m
Delta
Tue 7/75:20 pm
ATW
- BOS
1 stop5h 12m
Delta
Deal found 2/26![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/255:50 am
BDL
- ORD
2 stops10h 40m
Southwest
Mon 4/272:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Deal found 2/28![Southwest logo]()
$376
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/275:31 pm
BOS
- MSP
1 stop7h 42m
American Airlines
Sun 3/295:47 am
MSP
- BOS
1 stop5h 29m
American Airlines
Deal found 2/28![American Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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.
Mon 4/134:40 pm
BDL
- MKE
1 stop7h 30m
Southwest
Mon 4/273:50 pm
MKE
- BDL
2 stops6h 20m
Southwest
Deal found 2/27![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 7/299:05 am
BOS
- MSN
1 stop4h 49m
Delta
Tue 8/115:50 pm
MSN
- BOS
1 stop4h 42m
Delta
Deal found 2/26![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
BOS
- MKE
3 stops9h 14m
United Airlines
Tue 6/27:00 pm
MKE
- BOS
1 stop4h 59m
United Airlines
Deal found 2/28![United Airlines logo]()
$298
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 1, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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
Tue 3/310:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/27![JetBlue logo]()
$140
This KAYAK deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/25![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/36:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 3/47:30 am
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/27![United Airlines logo]()
$145
This Super.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/1110:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/25![JetBlue logo]()
$143
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/68:15 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Fri 4/36:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/27![United Airlines logo]()
$131
This American Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/1211:09 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Tue 3/247:40 pm
ORD
- BOS
Nonstop2h 21m
American Airlines
Deal found 2/26![American Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/174:25 pm
BOS
- ORD
Nonstop3h 06m
Delta
Tue 3/247:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/26![Delta logo]()
$136
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/184:25 pm
BOS
- ORD
Nonstop3h 06m
Delta
Mon 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/28![Delta logo]()
$141
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/267:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Mon 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/28![Delta logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 3/266:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/26![United Airlines logo]()
$146
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/286:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/27![United Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Mon 3/306:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Thu 4/27:40 pm
ORD
- BOS
Nonstop2h 21m
American Airlines
Deal found 3/1![American Airlines logo]()
$142
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 March 1, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 1, 2026.
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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 3/2012:10 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/27![United Airlines logo]()
$64
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 2/25![Frontier logo]()
$65
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- ORD
2 stops10h 30m
Southwest
Deal found 2/28![Southwest logo]()
$65
This Trip.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:07 pm
BDL
- ORD
1 stop10h 32m
Frontier
Deal found 2/28![Frontier logo]()
$66
This Super.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Mon 4/66:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 2/25![JetBlue logo]()
$66
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” 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 5/148:05 am
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 2/26![United Airlines logo]()
$67
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” 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.
Sun 3/87:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/27![JetBlue logo]()
$68
This Trip.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 2/27![Frontier logo]()
$69
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/288:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Deal found 2/28![Southwest logo]()
$69
This Trip.com deal was found by Cheapflights users on 3/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 3/1![Frontier logo]()
$70
This Cheapflightsfares deal was found by Cheapflights users on 3/1. 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.
Wed 4/228:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$70
This Southwest deal was found by Cheapflights users on 3/1. 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 5/165:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 3/1![Southwest logo]()
$71
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 March 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $128 (Southwest) |
One-way from | $64 (United Airlines) |
Popular in | November |
Cheapest in | September |
Average price | $369 |
Good round-trip deal | $287 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 March 1, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/26
7:00 am-8:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 8/29
7:00 am-10:28 am
Nonstop2h 28m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 3/29
7:15 am-9:14 am
Nonstop2h 59m
Chicago O'Hare Intl
Sun 4/5
7:30 am-11:01 am
Nonstop2h 31m
$142
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
Tue 4/14
7:35 pm-9:39 pm
Nonstop3h 04m
Chicago O'Hare Intl
Thu 4/16
8:31 am-2:18 pm
1 stop4h 47m
$171
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/29
6:20 am-4:05 pm
2 stops10h 45m
Chicago O'Hare Intl
Fri 5/1
2:40 pm-11:15 pm
1 stop7h 35m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 4/3
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 4/15
8:45 am-2:42 pm
1 stop4h 57m
$202
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 3/18
4:50 pm-6:40 pm
Nonstop2h 50m
Milwaukee-Mitchell
Mon 3/23
7:25 pm-10:41 pm
Nonstop2h 16m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 6/21
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 6/24
12:11 pm-5:57 pm
1 stop4h 46m
$213
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Thu 5/7
5:40 am-9:50 am
1 stop5h 10m
Milwaukee-Mitchell
Mon 5/11
3:30 pm-9:50 pm
1 stop5h 20m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 4/18
9:00 pm-10:55 pm
Nonstop2h 55m
Chicago O'Hare Intl
Tue 4/21
7:59 pm-11:27 pm
Nonstop2h 28m
$217
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Massachusetts with our price prediction graph.
BOS-ORD
BOS-MSP
BOS-GRB
BOS-MKE
ALB-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Wisconsin
USMA-USWI
BOS-ORD
BOS-MSP
BOS-GRB
BOS-MKE
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 March 1, 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 March 1, 2026.
The most flights from USMA to USWI are scheduled on a Friday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 March 1, 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.
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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.
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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 March 1, 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 March 1, 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% |