$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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jul 19 — Jul 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 June 19, 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 19, 2026.
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 am
MKE
- BOS
1 stop5h 01m
United Airlines
Sat 7/118:15 am
BOS
- MKE
1 stop7h 21m
United Airlines
Deal found 6/16![United Airlines logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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.
Sat 9/1211:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Tue 9/158:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/19![JetBlue logo]()
$199
This Cheapflightsfares 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 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
Wed 9/308:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/14![JetBlue logo]()
$202
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Sat 9/268:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 6/17![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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.
Sat 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/147:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/19![JetBlue logo]()
$209
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 8/87:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/17![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 Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 7/89:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 7/117:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/19![JetBlue logo]()
$214
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 7/87:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/17![JetBlue logo]()
$216
This Delta deal was found by Cheapflights users on 6/16. 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 9/226:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Tue 9/299:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Deal found 6/16![Delta logo]()
$217
This JetBlue 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 JetBlue 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
Mon 7/137:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/15![JetBlue logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/77:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/18![JetBlue logo]()
$219
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 19, 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 19, 2026.
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Fri 7/317:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Mon 8/36:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/19![United Airlines logo]()
$197
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 8/267:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/17![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 6/19. 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 8/276:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Mon 8/316:00 am
BOS
- MKE
1 stop7h 36m
Delta
Deal found 6/19![Delta logo]()
$227
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:50 pm
MKE
- ALB
1 stop6h 20m
Southwest
Wed 10/143:05 pm
ALB
- MKE
2 stops7h 50m
Southwest
Deal found 6/15![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
MKE
- BOS
1 stop5h 47m
United Airlines
Mon 9/147:00 pm
BOS
- MKE
1 stop5h 37m
United Airlines
Deal found 6/17![United Airlines logo]()
$197
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 7/184:57 pm
MKE
- BOS
1 stop6h 02m
Delta
Wed 7/226:00 am
BOS
- MKE
1 stop5h 07m
Delta
Deal found 6/14![Delta logo]()
$237
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 6/19. 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 8/61:18 pm
MKE
- BOS
1 stop7h 29m
Delta
Mon 8/105:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 6/19![Delta logo]()
$237
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 7/286:20 am
MKE
- BOS
2 stops7h 20m
United Airlines
Wed 7/296:00 am
BOS
- MKE
1 stop4h 53m
United Airlines
Deal found 6/14![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 6/17. 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.
Wed 8/126:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Fri 8/149:06 am
BOS
- MKE
1 stop4h 39m
Delta
Deal found 6/17![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 6/19. 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 8/125:00 am
MKE
- BOS
2 stops8h 22m
United Airlines
Fri 8/147:00 pm
BOS
- MKE
1 stop5h 37m
United Airlines
Deal found 6/19![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 6/16. 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 9/107:00 am
MKE
- BDL
2 stops8h 10m
Southwest
Wed 9/1612:45 pm
BDL
- MKE
2 stops8h 10m
Southwest
Deal found 6/16![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 6/19. 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 9/306:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sun 10/45:45 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 6/19![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/156:00 am
MKE
- BDL
1 stop4h 00m
Southwest
Fri 7/175:10 pm
BDL
- MKE
2 stops8h 10m
Southwest
Deal found 6/16![Southwest logo]()
$388
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 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 Delta deal was found by Cheapflights users on 6/16. 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.
Mon 7/2711:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Thu 7/305:30 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 6/16![Delta logo]()
$313
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:45 am
MKE
- ALB
1 stop4h 25m
Southwest
Sat 8/1511:25 am
ALB
- MKE
2 stops8h 00m
Southwest
Deal found 6/15![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Wed 9/166:00 am
BDL
- MKE
2 stops9h 33m
United Airlines
Deal found 6/16![United Airlines logo]()
$341
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:48 pm
MKE
- BOS
1 stop4h 11m
Delta
Sun 8/165:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 6/15![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sat 7/186:40 am
MKE
- ALB
1 stop8h 40m
Southwest
Mon 7/273:20 pm
ALB
- MKE
2 stops8h 40m
Southwest
Deal found 6/17![Southwest logo]()
$389
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
- BDL
1 stop4h 21m
United Airlines
Sat 8/156:00 am
BDL
- MKE
2 stops9h 33m
United Airlines
Deal found 6/15![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 6/16. 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.
Fri 7/37:00 am
MKE
- BDL
1 stop4h 00m
Southwest
Tue 7/72:35 pm
BDL
- MKE
2 stops8h 55m
Southwest
Deal found 6/16![Southwest logo]()
$402
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 10/82:50 pm
MKE
- ALB
1 stop6h 20m
Southwest
Mon 10/122:55 pm
ALB
- MKE
2 stops8h 25m
Southwest
Deal found 6/14![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Sun 8/166:00 am
BDL
- MKE
1 stop5h 00m
United Airlines
Deal found 6/17![United Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 9/49:40 am
MKE
- BDL
1 stop5h 40m
Delta
Sat 9/51:09 pm
BDL
- MKE
1 stop3h 53m
Delta
Deal found 6/17![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 6/17. 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.
Thu 10/225:50 am
MKE
- BDL
2 stops7h 45m
Southwest
Mon 10/263:10 pm
BDL
- MKE
2 stops9h 55m
Southwest
Deal found 6/17![Southwest logo]()
$414
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 8/17:11 am
MKE
- ALB
1 stop3h 45m
Delta
Sun 8/96:35 am
ALB
- MKE
1 stop4h 27m
Delta
Deal found 6/14![Delta logo]()
$384
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.
Tue 12/810:45 am
MKE
- ALB
1 stop5h 10m
United Airlines
Sat 12/126:15 am
ALB
- MKE
1 stop6h 19m
United Airlines
Deal found 6/15![United Airlines logo]()
$394
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 7/24:49 pm
MKE
- ALB
1 stop5h 35m
Delta
Tue 7/75:45 am
ALB
- MKE
1 stop5h 22m
Delta
Deal found 6/14![Delta logo]()
$385
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated June 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 6/306:50 pm
MKE
- BOS
1 stop4h 38m
American Airlines
Fri 7/31:01 pm
BOS
- MKE
1 stop7h 58m
American Airlines
Deal found 6/16![American Airlines logo]()
$207
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 7/45:00 am
MKE
- BOS
1 stop5h 01m
United Airlines
Tue 7/146:00 am
BOS
- MKE
1 stop4h 53m
United Airlines
Deal found 6/15![United Airlines logo]()
$197
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 7/87:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/17![JetBlue logo]()
$216
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/77:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/18![JetBlue logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:20 am
MKE
- BOS
2 stops7h 20m
United Airlines
Wed 7/86:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/17![United Airlines logo]()
$222
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:43 am
MKE
- BDL
1 stop25h 49m
Frontier
Wed 7/812:27 pm
BDL
- MKE
1 stop20h 31m
Frontier
Deal found 6/17![Frontier logo]()
$296
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 7/89:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/147:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/19![JetBlue logo]()
$214
This Delta deal was found by Cheapflights users on 6/17. 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.
Thu 7/911:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Sat 7/115:30 am
BOS
- MKE
1 stop4h 22m
Delta
Deal found 6/17![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Fri 7/106:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Deal found 6/17![United Airlines logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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.
Sat 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 7/147:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/19![JetBlue logo]()
$209
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 8/87:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/17![JetBlue logo]()
$212
This JetBlue 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 JetBlue 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
Mon 7/137:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 6/15![JetBlue logo]()
$218
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 19, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 19, 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.
Wed 8/1211:18 am
MKE
- BOS
1 stop7h 01m
United Airlines
Deal found 6/14![United Airlines logo]()
$99
This Super.com 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 Super.com 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
Deal found 6/14![JetBlue logo]()
$102
This Cheapflightsfares 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 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 6/15![JetBlue logo]()
$103
This Delta deal was found by Cheapflights users on 6/17. 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.
Sun 9/66:45 am
MKE
- MVY
1 stop4h 53m
Delta
Deal found 6/17![Delta logo]()
$103
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:00 am
MKE
- BOS
2 stops6h 47m
United Airlines
Deal found 6/16![United Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 6/18. 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.
Sat 7/119:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/18![JetBlue logo]()
$106
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/149:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/17![JetBlue logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 6/19![JetBlue logo]()
$108
This Delta deal was found by Cheapflights users on 6/18. 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.
Tue 7/1411:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Deal found 6/18![Delta logo]()
$109
This Super.com deal was found by Cheapflights users on 6/19. 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.
Sat 7/49:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 6/19![JetBlue logo]()
$112
This Cheapflightsfares 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 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
Deal found 6/15![JetBlue logo]()
$113
This Delta deal was found by Cheapflights users on 6/18. 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 9/106:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Deal found 6/18![Delta logo]()
$114
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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (United Airlines) |
One-way from | $99 (United Airlines) |
Popular in | February |
Cheapest in | May |
Average price | $259 |
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 19, 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
Fri 7/31
7:23 pm-1:14 am
1 stop4h 51m
Boston Logan Intl
Mon 8/3
6:43 pm-10:29 pm
1 stop4h 46m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 9/10
6:00 am-12:47 pm
1 stop5h 47m
Boston Logan Intl
Mon 9/14
7:00 pm-11:37 pm
1 stop5h 37m
$197
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 8/25
9:36 am-12:49 pm
Nonstop2h 13m
Boston Logan Intl
Wed 8/26
7:10 am-8:45 am
Nonstop2h 35m
$217
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 8/27
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Mon 8/31
6:00 am-12:36 pm
1 stop7h 36m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 7/18
4:57 pm-11:59 pm
1 stop6h 02m
Boston Logan Intl
Wed 7/22
6:00 am-10:07 am
1 stop5h 07m
$237
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 8/6
1:18 pm-9:47 pm
1 stop7h 29m
Boston Logan Intl
Mon 8/10
5:30 am-8:55 am
1 stop4h 25m
$237
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/12
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Fri 8/14
9:06 am-12:45 pm
1 stop4h 39m
$257
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 7/28
6:20 am-2:40 pm
2 stops7h 20m
Boston Logan Intl
Wed 7/29
6:00 am-9:53 am
1 stop4h 53m
$282
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/12
5:00 am-2:22 pm
2 stops8h 22m
Boston Logan Intl
Fri 8/14
7:00 pm-11:37 pm
1 stop5h 37m
$282
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 9/30
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Sun 10/4
5:45 am-8:53 am
1 stop4h 08m
$313
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-MVY
MKE-BDL
MKE-ALB
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-MVY
MKE-BDL
MKE-ALB
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 19, 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.
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 19, 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
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
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
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Massachusetts by cabin class
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 19, 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 19, 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% |