$99+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 19 — Aug 261
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 July 20, 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 July 20, 2026.
This SmartFares deal was found by Cheapflights users on 7/19. 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.
Sat 9/2611:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Wed 9/308:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/19![JetBlue logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Sat 9/268:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/15![JetBlue logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 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 7/15![JetBlue logo]()
$205
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue 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
Wed 9/168:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/15![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/59:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 9/148:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/17![JetBlue logo]()
$215
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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
Wed 9/305:40 am
BOS
- MKE
1 stop4h 12m
Delta
Deal found 7/16![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Wed 9/165:00 am
MKE
- BOS
2 stops6h 47m
United Airlines
Sat 9/197:46 am
BOS
- MKE
1 stop4h 44m
United Airlines
Deal found 7/15![United Airlines logo]()
$222
This Priceline deal was found by Cheapflights users on 7/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:36 am
MKE
- BOS
Nonstop2h 13m
Multiple Airlines
Mon 9/1411:05 am
BOS
- MKE
1 stop9h 10m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:47 pm
MKE
- BOS
1 stop4h 30m
Delta
Sat 9/267:00 am
BOS
- MKE
1 stop5h 37m
Delta
Deal found 7/15![Delta logo]()
$227
This CheapOair deal was found by Cheapflights users on 7/15. 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.
Wed 9/3011:25 am
MKE
- BOS
Nonstop2h 39m
Multiple Airlines
Sun 10/411:05 am
BOS
- MKE
1 stop9h 10m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$228
This Priceline deal was found by Cheapflights users on 7/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:25 am
MKE
- BOS
Nonstop2h 39m
Multiple Airlines
Fri 10/169:15 am
BOS
- MKE
1 stop11h 00m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/18:20 am
MKE
- BOS
1 stop7h 35m
Southwest
Sat 9/1212:10 pm
BOS
- MKE
2 stops7h 15m
Southwest
Deal found 7/16![Southwest logo]()
$232
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 July 20, 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 July 20, 2026.
This Delta deal was found by Cheapflights users on 7/19. 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.
Sat 8/294:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Tue 9/16:59 am
BOS
- MKE
1 stop6h 37m
Delta
Deal found 7/19![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/18. 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.
Tue 9/16:40 am
MKE
- BOS
2 stops7h 00m
Southwest
Tue 9/85:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Deal found 7/18![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Wed 8/126:15 am
MKE
- BOS
2 stops7h 35m
United Airlines
Sat 8/156:00 pm
BOS
- MKE
1 stop6h 37m
United Airlines
Deal found 7/15![United Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/16:01 am
MKE
- ALB
1 stop7h 35m
American Airlines
Mon 10/57:17 pm
ALB
- MKE
1 stop4h 57m
American Airlines
Deal found 7/16![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/164:57 pm
MKE
- BOS
1 stop6h 01m
Delta
Wed 9/237:00 am
BOS
- MKE
1 stop6h 43m
Delta
Deal found 7/16![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 10/142:20 pm
MKE
- BOS
2 stops7h 20m
Southwest
Fri 10/1610:40 am
BOS
- MKE
2 stops14h 55m
Southwest
Deal found 7/17![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Sat 9/126:47 pm
MKE
- BOS
1 stop4h 47m
United Airlines
Wed 9/1610:38 am
BOS
- MKE
1 stop5h 33m
United Airlines
Deal found 7/18![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:40 am
MKE
- ALB
1 stop3h 55m
Southwest
Sat 9/198:30 am
ALB
- MKE
2 stops9h 00m
Southwest
Deal found 7/15![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Wed 9/1610:30 am
MKE
- BOS
2 stops7h 49m
United Airlines
Wed 9/236:00 am
BOS
- MKE
1 stop5h 00m
United Airlines
Deal found 7/19![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 7/19. 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 8/2011:31 am
MKE
- BOS
Nonstop2h 28m
Delta
Sun 8/235:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 7/19![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:30 pm
MKE
- BDL
1 stop4h 10m
Southwest
Sat 9/121:15 pm
BDL
- MKE
1 stop6h 10m
Southwest
Deal found 7/15![Southwest logo]()
$317
This KAYAK deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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.
Fri 7/319:35 am
MKE
- PVC
1 stop4h 35m
Multiple Airlines
Mon 8/101:41 pm
PVC
- MKE
1 stop20h 03m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$784
This United Airlines deal was found by Cheapflights users on 7/18. 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 8/175:17 pm
MKE
- BOS
1 stop5h 17m
United Airlines
Sat 8/225:45 am
BOS
- MKE
2 stops7h 53m
United Airlines
Deal found 7/18![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:47 pm
MKE
- ALB
1 stop5h 18m
Delta
Sun 8/306:35 am
ALB
- MKE
1 stop4h 27m
Delta
Deal found 7/15![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:25 pm
MKE
- BOS
2 stops8h 40m
Southwest
Sat 10/105:25 am
BOS
- MKE
1 stop5h 15m
Southwest
Deal found 7/15![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Thu 9/36:00 am
MKE
- BOS
1 stop5h 47m
United Airlines
Tue 9/85:45 am
BOS
- MKE
2 stops6h 45m
United Airlines
Deal found 7/19![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/19. 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.
Wed 8/58:20 am
MKE
- BOS
1 stop7h 35m
Southwest
Tue 8/1110:50 am
BOS
- MKE
2 stops10h 05m
Southwest
Deal found 7/19![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 7/18. 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.
Thu 9/177:14 am
MKE
- ALB
1 stop4h 10m
Delta
Sun 9/209:36 am
ALB
- MKE
1 stop4h 12m
Delta
Deal found 7/18![Delta logo]()
$356
This United Airlines deal was found by Cheapflights users on 7/15. 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 8/275:00 am
MKE
- ALB
1 stop4h 24m
United Airlines
Sun 8/306:00 am
ALB
- MKE
1 stop5h 00m
United Airlines
Deal found 7/15![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/245:45 am
MKE
- ALB
1 stop4h 25m
Southwest
Mon 8/246:05 pm
ALB
- MKE
1 stop4h 20m
Southwest
Deal found 7/16![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 7/18. 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 9/247:18 am
MKE
- BDL
1 stop6h 11m
United Airlines
Mon 9/285:03 pm
BDL
- MKE
1 stop6h 56m
United Airlines
Deal found 7/18![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:00 pm
MKE
- BDL
1 stop6h 45m
Southwest
Mon 9/146:20 pm
BDL
- MKE
1 stop4h 05m
Southwest
Deal found 7/17![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Thu 9/175:00 am
MKE
- ALB
1 stop4h 24m
United Airlines
Sun 9/206:00 am
ALB
- MKE
1 stop5h 00m
United Airlines
Deal found 7/19![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 11/56:55 am
MKE
- ALB
1 stop4h 05m
Southwest
Sun 11/88:35 am
ALB
- MKE
1 stop9h 55m
Southwest
Deal found 7/16![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 7/15. 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 9/35:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Sun 9/610:33 am
BDL
- MKE
2 stops9h 22m
United Airlines
Deal found 7/15![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 7/19. 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.
Tue 8/1810:30 am
MKE
- ALB
2 stops9h 30m
Southwest
Mon 8/243:10 pm
ALB
- MKE
2 stops6h 05m
Southwest
Deal found 7/19![Southwest logo]()
$351
This KAYAK deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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.
Sat 8/19:35 am
MKE
- PVC
1 stop9h 33m
Multiple Airlines
Mon 8/101:41 pm
PVC
- MKE
1 stop20h 03m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$814
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:30 am
MKE
- ALB
2 stops9h 30m
Southwest
Sun 8/306:10 am
ALB
- MKE
2 stops8h 25m
Southwest
Deal found 7/15![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 8/1110:19 am
MKE
- BDL
1 stop7h 01m
United Airlines
Wed 8/126:00 am
BDL
- MKE
1 stop5h 00m
United Airlines
Deal found 7/15![United Airlines logo]()
$407
This KAYAK deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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.
Sun 8/29:35 am
MKE
- PVC
1 stop8h 15m
Multiple Airlines
Mon 8/101:41 pm
PVC
- MKE
1 stop20h 03m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$824
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 20, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 20, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 7/15. 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 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
Tue 8/47:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 7/15![JetBlue logo]()
$244
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Wed 8/54:20 pm
BOS
- MKE
Nonstop2h 52m
Delta
Deal found 7/15![Delta logo]()
$207
This Super.com deal was found by Cheapflights users on 7/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 8/117:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/19![JetBlue logo]()
$215
This CheapOair deal was found by Cheapflights users on 7/15. 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.
Thu 8/68:43 am
MKE
- BOS
1 stop23h 26m
Multiple Airlines
Tue 8/117:10 am
BOS
- MKE
Nonstop2h 34m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$234
This Priceline deal was found by Cheapflights users on 7/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 8/117:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/15![JetBlue logo]()
$237
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Thu 8/611:32 am
MKE
- BOS
1 stop6h 08m
American Airlines
Tue 8/118:27 am
BOS
- MKE
1 stop6h 59m
American Airlines
Deal found 7/15![American Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Tue 8/186:00 pm
BOS
- MKE
1 stop5h 30m
Delta
Deal found 7/15![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/113:10 pm
MKE
- BOS
2 stops6h 05m
Southwest
Tue 8/185:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Deal found 7/17![Southwest logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 8/157:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/15![JetBlue logo]()
$239
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Sat 8/225:30 am
BOS
- MKE
1 stop4h 15m
Delta
Deal found 7/16![Delta logo]()
$227
This CheapOair deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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.
Sun 8/168:43 am
MKE
- BOS
1 stop23h 26m
Multiple Airlines
Sat 8/227:10 am
BOS
- MKE
Nonstop2h 34m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$238
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 9/98:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/15![JetBlue logo]()
$205
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 July 20, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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 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
Deal found 7/15![JetBlue logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/19![JetBlue logo]()
$102
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/186:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/16![Delta logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/15![JetBlue logo]()
$107
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Deal found 7/15![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/121:18 pm
MKE
- BOS
1 stop7h 29m
Delta
Deal found 7/16![Delta logo]()
$114
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 8/47:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 7/15![United Airlines logo]()
$119
This Super.com deal was found by Cheapflights users on 7/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:43 am
MKE
- BOS
1 stop23h 26m
Frontier
Deal found 7/18![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:10 pm
MKE
- BOS
1 stop11h 10m
Frontier
Deal found 7/19![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:43 am
MKE
- BOS
1 stop23h 26m
Frontier
Deal found 7/15![Frontier logo]()
$128
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 11/94:50 pm
MKE
- ALB
1 stop4h 00m
Southwest
Deal found 7/16![Southwest logo]()
$152
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/124:57 pm
MKE
- BDL
1 stop5h 16m
Delta
Deal found 7/17![Delta logo]()
$159
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 July 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (SmartFares) |
One-way from | $99 (JetBlue) |
Popular in | February |
Cheapest in | May |
Average price | $297 |
Good round-trip deal | $228 or less |
Good one-way deal | $148 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 July 20, 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
Sat 8/29
4:47 pm-11:59 pm
1 stop6h 12m
Boston Logan Intl
Tue 9/1
6:59 am-12:36 pm
1 stop6h 37m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 9/16
4:57 pm-11:58 pm
1 stop6h 01m
Boston Logan Intl
Wed 9/23
7:00 am-12:43 pm
1 stop6h 43m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 9/1
6:40 am-2:40 pm
2 stops7h 00m
Boston Logan Intl
Tue 9/8
5:35 am-9:40 am
1 stop5h 05m
$232
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/12
6:15 am-2:50 pm
2 stops7h 35m
Boston Logan Intl
Sat 8/15
6:00 pm-11:37 pm
1 stop6h 37m
$302
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 10/14
2:20 pm-10:40 pm
2 stops7h 20m
Boston Logan Intl
Fri 10/16
10:40 am-12:35 am
2 stops14h 55m
$302
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 9/12
6:47 pm-12:34 am
1 stop4h 47m
Boston Logan Intl
Wed 9/16
10:38 am-3:11 pm
1 stop5h 33m
$307
MilwaukeeAlbany
MKE - ALB
MKEALB
Milwaukee-Mitchell
Wed 9/16
6:40 am-11:35 am
1 stop3h 55m
Albany Intl
Sat 9/19
8:30 am-4:30 pm
2 stops9h 00m
$308
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 9/16
10:30 am-7:19 pm
2 stops7h 49m
Boston Logan Intl
Wed 9/23
6:00 am-10:00 am
1 stop5h 00m
$312
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Thu 9/10
12:30 pm-5:40 pm
1 stop4h 10m
Hartford Bradley Intl
Sat 9/12
1:15 pm-6:25 pm
1 stop6h 10m
$317
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 10/5
2:25 pm-12:05 am
2 stops8h 40m
Boston Logan Intl
Sat 10/10
5:25 am-9:40 am
1 stop5h 15m
$317
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-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-PVC
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $234). Flying from Milwaukee to Massachusetts in February is currently the most expensive (average of $419). 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 July 20, 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 40% 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 July 20, 2026.
The most flights from MKE to USMA are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 July 18, 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 July 20, 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.
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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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Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on July 20, 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 July 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$111 | Average$356 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$168 | Average$296 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$303 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$307 | FlexibilityNo cancel fee | On-time63% |