$95+ Cheap flights from Milwaukee (MKE) 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jul 15 — Jul 221
Round-trip
1 adult, Economy
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Cheapest flights from Milwaukee to MassachusettsExplore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
Explore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/307:24 pm
MKE
- BOS
1 stop4h 50m
United Airlines
Sat 7/48:15 am
BOS
- MKE
1 stop5h 33m
United Airlines
Deal found 6/14![United Airlines logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/2311:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Sat 9/268:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/10![JetBlue logo]()
$202
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/65:45 am
MKE
- BOS
1 stop4h 50m
Southwest
Tue 10/135:10 pm
BOS
- MKE
1 stop6h 00m
Southwest
Deal found 6/11![Southwest logo]()
$204
This JetBlue deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 9/1511:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Tue 9/228:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/13![JetBlue logo]()
$207
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/237:50 am
MKE
- BOS
1 stop7h 10m
Southwest
Wed 9/3010:50 am
BOS
- MKE
2 stops10h 05m
Southwest
Deal found 6/11![Southwest logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/147:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/10![JetBlue logo]()
$212
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 11/55:00 am
MKE
- BOS
1 stop4h 53m
United Airlines
Mon 11/98:10 pm
BOS
- MKE
1 stop4h 59m
United Airlines
Deal found 6/14![United Airlines logo]()
$213
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/77:50 am
MKE
- BOS
1 stop5h 17m
United Airlines
Sat 7/116:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/13![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/236:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sat 9/265:45 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 6/10![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/37:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Sat 7/119:50 am
BOS
- MKE
1 stop6h 46m
United Airlines
Deal found 6/11![United Airlines logo]()
$218
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/299:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/37:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/11![JetBlue logo]()
$222
This CheapOair deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- BOS
1 stop23h 26m
Multiple Airlines
Tue 8/117:10 am
BOS
- MKE
Nonstop2h 35m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$224
Best flights from Milwaukee to MassachusettsDiscover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/307:24 pm
MKE
- BOS
1 stop4h 50m
United Airlines
Sat 7/48:15 am
BOS
- MKE
1 stop5h 33m
United Airlines
Deal found 6/14![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/911:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Mon 7/135:30 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 6/11![Delta logo]()
$227
This JetBlue deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/309:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/37:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/12![JetBlue logo]()
$282
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/217:45 am
MKE
- ALB
1 stop5h 40m
Southwest
Tue 7/286:55 pm
ALB
- MKE
1 stop4h 00m
Southwest
Deal found 6/11![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 8/276:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Sat 9/57:15 am
BOS
- MKE
1 stop6h 30m
Delta
Deal found 6/13![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/112:12 pm
MKE
- BOS
Nonstop2h 22m
Delta
Tue 7/2811:00 am
BOS
- MKE
1 stop7h 07m
Delta
Deal found 6/14![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/136:00 am
MKE
- MVY
1 stop4h 52m
American Airlines
Mon 7/2012:22 pm
MVY
- MKE
2 stops10h 32m
American Airlines
Deal found 6/15![American Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/911:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Thu 7/235:30 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 6/14![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/15:29 pm
MKE
- BOS
1 stop6h 45m
United Airlines
Sat 7/45:45 am
BOS
- MKE
2 stops10h 51m
United Airlines
Deal found 6/14![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/96:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Tue 7/146:00 am
BOS
- MKE
1 stop5h 07m
Delta
Deal found 6/10![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/296:00 am
MKE
- BOS
1 stop5h 50m
United Airlines
Tue 9/16:00 am
BOS
- MKE
3 stops11h 10m
United Airlines
Deal found 6/12![United Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/286:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Wed 7/296:00 am
BOS
- MKE
1 stop7h 36m
Delta
Deal found 6/10![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/286:00 am
MKE
- ALB
2 stops7h 25m
Southwest
Tue 8/49:05 am
ALB
- MKE
1 stop8h 15m
Southwest
Deal found 6/13![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/216:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Mon 8/245:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 6/11![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/65:00 am
MKE
- ALB
1 stop4h 43m
United Airlines
Sat 8/156:00 am
ALB
- MKE
1 stop5h 00m
United Airlines
Deal found 6/15![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/16:50 pm
MKE
- ALB
1 stop4h 15m
Southwest
Sun 10/116:00 am
ALB
- MKE
1 stop5h 35m
Southwest
Deal found 6/11![Southwest logo]()
$365
This United deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/57:23 pm
MKE
- PVC
2 stops12h 06m
Multiple Airlines
Fri 8/78:49 am
PVC
- MKE
2 stops11h 37m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$890
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/299:35 am
MKE
- BDL
1 stop7h 15m
Southwest
Thu 7/307:10 pm
BDL
- MKE
1 stop4h 40m
Southwest
Deal found 6/10![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/216:45 am
MKE
- MVY
1 stop4h 53m
Delta
Fri 8/281:18 pm
MVY
- MKE
1 stop7h 06m
Delta
Deal found 6/11![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/15:00 am
MKE
- ALB
1 stop4h 24m
United Airlines
Wed 9/28:10 am
ALB
- MKE
1 stop5h 28m
United Airlines
Deal found 6/11![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/135:45 am
MKE
- ALB
1 stop4h 25m
Southwest
Mon 8/176:30 am
ALB
- MKE
2 stops9h 55m
Southwest
Deal found 6/14![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/15:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Sat 9/56:00 am
BDL
- MKE
1 stop5h 00m
United Airlines
Deal found 6/10![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/294:47 pm
MKE
- BDL
1 stop6h 04m
Delta
Tue 9/15:05 pm
BDL
- MKE
1 stop4h 13m
Delta
Deal found 6/10![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/105:40 am
MKE
- BDL
1 stop4h 15m
Southwest
Tue 7/147:55 am
BDL
- MKE
1 stop4h 00m
Southwest
Deal found 6/11![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/297:20 am
MKE
- BDL
1 stop6h 09m
United Airlines
Tue 9/16:00 am
BDL
- MKE
2 stops11h 10m
United Airlines
Deal found 6/10![United Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/86:48 pm
MKE
- MVY
2 stops14h 23m
American Airlines
Wed 8/125:25 pm
MVY
- MKE
1 stop7h 31m
American Airlines
Deal found 6/12![American Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/176:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Mon 7/205:30 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 6/13![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/76:00 am
MKE
- BDL
2 stops7h 00m
Southwest
Mon 7/135:10 pm
BDL
- MKE
2 stops8h 10m
Southwest
Deal found 6/13![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 10/225:50 am
MKE
- BDL
1 stop4h 05m
Southwest
Sat 10/2412:10 pm
BDL
- MKE
2 stops8h 45m
Southwest
Deal found 6/14![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 12/82:50 pm
MKE
- BDL
1 stop5h 32m
United Airlines
Wed 12/96:15 am
BDL
- MKE
1 stop6h 19m
United Airlines
Deal found 6/14![United Airlines logo]()
$397
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated June 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/246:01 am
MKE
- BOS
1 stop7h 40m
American Airlines
Mon 6/295:23 pm
BOS
- MKE
1 stop6h 44m
American Airlines
Deal found 6/10![American Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/296:49 pm
MKE
- BOS
1 stop4h 05m
Delta
Tue 7/79:10 am
BOS
- MKE
Nonstop2h 44m
Delta
Deal found 6/10![Delta logo]()
$232
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 6/307:24 pm
MKE
- BOS
1 stop4h 50m
United Airlines
Sat 7/48:15 am
BOS
- MKE
1 stop5h 33m
United Airlines
Deal found 6/14![United Airlines logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/19:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/77:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/11![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/37:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Sat 7/119:50 am
BOS
- MKE
1 stop6h 46m
United Airlines
Deal found 6/11![United Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/77:50 am
MKE
- BOS
1 stop5h 17m
United Airlines
Sat 7/116:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/13![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/96:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Tue 7/146:00 am
BOS
- MKE
1 stop5h 07m
Delta
Deal found 6/11![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/94:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Mon 7/135:30 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 6/11![Delta logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/147:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/10![JetBlue logo]()
$212
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/116:14 am
MKE
- BOS
1 stop6h 18m
United Airlines
Tue 7/146:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/15![United Airlines logo]()
$213
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/299:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/37:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/11![JetBlue logo]()
$222
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/306:45 pm
MKE
- BOS
1 stop4h 25m
Southwest
Tue 8/45:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Deal found 6/11![Southwest logo]()
$235
One-way flights from Milwaukee to MassachusettsSearch for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This SmartFares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Wed 7/89:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/10![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/107:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 6/10![United Airlines logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 9/1211:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Deal found 6/13![JetBlue logo]()
$103
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/125:00 am
MKE
- BOS
2 stops6h 47m
United Airlines
Deal found 6/15![United Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/10![JetBlue logo]()
$108
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/96:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 6/11![Delta logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/309:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/10![JetBlue logo]()
$113
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/92:00 pm
MKE
- BOS
1 stop7h 27m
Delta
Deal found 6/11![Delta logo]()
$114
This CheapOair deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- BOS
1 stop23h 26m
Frontier
Deal found 6/15![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/101:18 pm
MKE
- BOS
1 stop5h 23m
Delta
Deal found 6/10![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/107:00 am
MKE
- BOS
1 stop7h 19m
Delta
Deal found 6/11![Delta logo]()
$124
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/136:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 6/12![Delta logo]()
$129
Find flight deals from Milwaukee to Massachusetts
Keep the following information in mind while searching for Milwaukee to Massachusetts flight deals. Data was last updated June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (United Airlines) |
One-way from | $95 (SmartFares) |
Popular in | February |
Cheapest in | September |
Average price | $257 |
Good round-trip deal | $227 or less |
Good one-way deal | $113 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee 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 June 15, 2026.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 6/30
7:24 pm-1:14 am
1 stop4h 50m
Boston Logan Intl
Sat 7/4
8:15 am-12:48 pm
1 stop5h 33m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 7/9
11:35 am-3:05 pm
Nonstop2h 30m
Boston Logan Intl
Mon 7/13
5:30 am-8:39 am
1 stop4h 09m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 8/27
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Sat 9/5
7:15 am-12:45 pm
1 stop6h 30m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 7/11
2:12 pm-5:34 pm
Nonstop2h 22m
Boston Logan Intl
Tue 7/28
11:00 am-5:07 pm
1 stop7h 07m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 7/9
11:35 am-3:05 pm
Nonstop2h 30m
Boston Logan Intl
Thu 7/23
5:30 am-8:39 am
1 stop4h 09m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 7/9
6:59 pm-10:26 pm
Nonstop2h 27m
Boston Logan Intl
Tue 7/14
6:00 am-10:07 am
1 stop5h 07m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 7/28
6:59 pm-10:26 pm
Nonstop2h 27m
Boston Logan Intl
Wed 7/29
6:00 am-12:36 pm
1 stop7h 36m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 8/21
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Mon 8/24
5:30 am-8:55 am
1 stop4h 25m
$242
MilwaukeeWest Tisbury
MKE - MVY
MKEMVY
Milwaukee-Mitchell
Fri 8/21
6:45 am-12:38 pm
1 stop4h 53m
West Tisbury Martha's Vineyard
Fri 8/28
1:18 pm-7:24 pm
1 stop7h 06m
$266
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 7/30
9:35 am-12:48 pm
Nonstop2h 13m
Boston Logan Intl
Mon 8/3
7:10 am-8:45 am
Nonstop2h 35m
$282
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Milwaukee with our price prediction graph.
MKE-BOS
MKE-ALB
MKE-BDL
MKE-MVY
MKE-PVC
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 Milwaukee to Massachusetts
MKE-USMA
MKE-BOS
MKE-ALB
MKE-BDL
MKE-MVY
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $68). Flying from Milwaukee 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 MKE to MA?
Find hourly flight availability from Milwaukee 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 June 15, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the afternoon. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight at noon.
Weekly flight availability from Milwaukee to Massachusetts
Explore weekly flight availability from Milwaukee 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 June 15, 2026.
The most flights from MKE to USMA are scheduled on a Monday (9 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Milwaukee to Massachusetts?
How far ahead should I book a flight from Milwaukee to Massachusetts?
To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Milwaukee to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Massachusetts. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Milwaukee 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 June 15, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Milwaukee 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 Milwaukee to Massachusetts
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Complete your trip
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Find flights from Milwaukee to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on June 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Milwaukee to Massachusetts flights
Consider these flights traveling from Milwaukee to Massachusetts.
Top 5 airlines flying from Milwaukee to Massachusetts
Discover the top 5 airlines that operate flights from Milwaukee 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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$106 | Average$361 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$168 | Average$313 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$289 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$181 | Average$262 | FlexibilityNo cancel fee | On-time63% |