$68+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Apr 22 — Apr 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Wisconsin to Massachusetts
Cheapest
Best
Last-minute
One-way
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 March 23, 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 March 23, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sun 4/266:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/23![American Airlines logo]()
$146
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2110:15 am
ORD
- BOS
Nonstop2h 20m
Delta
Fri 4/247:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/23![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:45 pm
ORD
- BOS
Nonstop2h 30m
American Airlines
Tue 6/23:00 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 3/23![American Airlines logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sat 5/3011:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/22![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/19![JetBlue logo]()
$155
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sun 5/36:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/23![American Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 3/20![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:15 am
ORD
- BOS
Nonstop2h 20m
Delta
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 3/23![Delta logo]()
$158
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
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 March 23, 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 March 23, 2026.
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Mon 4/277:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/23![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Tue 5/59:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/18![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Mon 5/48:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/21![Southwest logo]()
$177
This JetBlue deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Mon 5/42:25 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/22![JetBlue logo]()
$207
This Sun Country Air deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:40 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Fri 7/1011:40 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 3/19![Sun Country Air logo]()
$254
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 5/316:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/21![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:00 pm
MKE
- BOS
1 stop5h 29m
Delta
Wed 6/35:40 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 3/22![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Mon 5/115:30 am
BOS
- ORD
2 stops8h 20m
Southwest
Deal found 3/21![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:41 pm
MKE
- BOS
1 stop4h 18m
United Airlines
Thu 4/96:00 am
BOS
- MKE
1 stop5h 00m
United Airlines
Deal found 3/18![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Mon 5/45:30 am
BOS
- MKE
1 stop4h 20m
Delta
Deal found 3/21![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:25 am
MKE
- BOS
2 stops13h 25m
Southwest
Mon 5/113:45 pm
BOS
- MKE
1 stop7h 30m
Southwest
Deal found 3/19![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:37 am
MKE
- BOS
1 stop5h 39m
United Airlines
Wed 5/1310:45 am
BOS
- MKE
1 stop4h 42m
United Airlines
Deal found 3/19![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 3/19![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/22![United Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/111:17 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Sat 4/46:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/18![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 6/65:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 3/18![Delta logo]()
$227
This Sun Country Air deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Sun 6/2811:40 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 3/19![Sun Country Air logo]()
$304
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Mon 5/47:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/18![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:50 am
MKE
- BOS
2 stops7h 00m
Southwest
Wed 5/202:25 pm
BOS
- MKE
2 stops9h 10m
Southwest
Deal found 3/23![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:35 pm
MKE
- BOS
1 stop3h 54m
Delta
Sat 6/65:40 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 3/21![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Fri 4/39:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/22![United Airlines logo]()
$205
This Sun Country Air deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Mon 7/66:50 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Deal found 3/22![Sun Country Air logo]()
$334
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:10 am
MKE
- BOS
1 stop6h 35m
Southwest
Tue 4/72:25 pm
BOS
- MKE
2 stops9h 10m
Southwest
Deal found 3/22![Southwest logo]()
$302
This Sun Country Air deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/165:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Mon 8/2411:40 am
BOS
- MSP
Nonstop3h 13m
Sun Country Air
Deal found 3/19![Sun Country Air logo]()
$334
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 6/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/22![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Tue 5/195:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Deal found 3/21![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Sat 6/65:51 am
BOS
- ATW
1 stop7h 00m
Delta
Deal found 3/22![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:40 pm
ORD
- ALB
2 stops7h 35m
Southwest
Sun 5/3112:25 pm
ALB
- ORD
2 stops10h 30m
Southwest
Deal found 3/18![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Fri 5/295:51 am
BOS
- ATW
1 stop7h 00m
Delta
Deal found 3/20![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:43 pm
ATW
- BOS
1 stop6h 16m
United Airlines
Mon 5/48:25 pm
BOS
- ATW
1 stop4h 49m
United Airlines
Deal found 3/18![United Airlines logo]()
$277
Last-minute flights from Wisconsin to MassachusettsDiscover last-minute flight deals from Wisconsin to Massachusetts. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Massachusetts. Data last updated March 23, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/19![JetBlue logo]()
$155
This SmartFares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Mon 4/136:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/19![JetBlue logo]()
$156
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:31 pm
ORD
- BOS
1 stop7h 55m
Frontier
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Deal found 3/20![Frontier logo]()
$161
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$158
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2110:15 am
ORD
- BOS
Nonstop2h 20m
Delta
Sat 4/258:59 pm
BOS
- ORD
Nonstop2h 51m
Delta
Deal found 3/23![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Fri 4/247:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/23![American Airlines logo]()
$146
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Fri 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Frontier
Deal found 3/23![Frontier logo]()
$160
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Mon 5/48:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Deal found 3/20![United Airlines logo]()
$157
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 March 23, 2026.
Search for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:39 pm
ORD
- BOS
Nonstop2h 33m
American Airlines
Deal found 3/23![American Airlines logo]()
$68
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Deal found 3/23![Delta logo]()
$69
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/23![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:13 pm
MKE
- BOS
1 stop7h 18m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- BDL
1 stop5h 49m
Frontier
Deal found 3/23![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/20![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 3/23![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/22![JetBlue logo]()
$78
This Super.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:58 pm
MKE
- BOS
Nonstop2h 17m
JetBlue
Deal found 3/23![JetBlue logo]()
$78
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/19![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 3/22![Delta logo]()
$79
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:06 am
ORD
- BOS
1 stop8h 03m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$80
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 March 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $68 (American Airlines) |
Popular in | February |
Cheapest in | September |
Average price | $368 |
Good round-trip deal | $226 or less |
Good one-way deal | $158 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 March 23, 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
Sun 4/19
6:50 am-10:11 am
Nonstop2h 21m
Boston Logan Intl
Mon 4/27
7:35 pm-9:29 pm
Nonstop2h 54m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/1
8:00 pm-11:35 pm
Nonstop2h 35m
Boston Logan Intl
Tue 5/5
9:20 am-11:20 am
Nonstop3h 00m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/27
9:26 pm-12:59 am
Nonstop2h 33m
Boston Logan Intl
Sun 5/31
6:00 am-7:58 am
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/30
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Mon 5/4
8:25 am-12:50 pm
1 stop5h 25m
$177
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 5/30
5:00 pm-11:29 pm
1 stop5h 29m
Boston Logan Intl
Wed 6/3
5:40 am-8:49 am
1 stop4h 09m
$177
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 4/6
7:41 pm-12:59 am
1 stop4h 18m
Boston Logan Intl
Thu 4/9
6:00 am-10:00 am
1 stop5h 00m
$177
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 5/12
9:37 am-4:16 pm
1 stop5h 39m
Boston Logan Intl
Wed 5/13
10:45 am-2:27 pm
1 stop4h 42m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/8
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Mon 5/11
5:30 am-12:50 pm
2 stops8h 20m
$182
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/1
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Mon 5/4
5:30 am-8:50 am
1 stop4h 20m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/27
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Fri 5/29
8:40 pm-10:35 pm
Nonstop2h 55m
$187
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.
ORD-BOS
MKE-BOS
ORD-BDL
MSP-BDL
ATW-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
MKE-BOS
ORD-BDL
MSP-BDL
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 March 23, 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 43% 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 March 23, 2026.
Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Saturday afternoons 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 March 23, 2026.
The most flights from USWI to USMA are scheduled on a Monday (6 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).
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 March 23, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
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 March 23, 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 March 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$105 | Average$362 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$263 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$178 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$382 | FlexibilityNo cancel fee | On-time69% |