$102+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 24 — Aug 311
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 25, 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 25, 2026.
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com 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
Sat 9/198:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/20![JetBlue logo]()
$205
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/20![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 9/17:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$215
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 9/148:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/21![JetBlue logo]()
$218
This Priceline deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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
Multiple Airlines
Fri 9/1811:05 am
BOS
- MKE
1 stop9h 10m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$225
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sat 9/195:40 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 7/22![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 am
MKE
- BOS
1 stop4h 32m
American Airlines
Sat 9/126:00 am
BOS
- MKE
1 stop4h 46m
American Airlines
Deal found 7/21![American Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:40 am
MKE
- BOS
2 stops8h 20m
Southwest
Tue 9/85:35 am
BOS
- MKE
1 stop5h 05m
Southwest
Deal found 7/20![Southwest logo]()
$232
This Priceline deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 10/129:15 am
BOS
- MKE
1 stop11h 00m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$233
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:10 pm
MKE
- BDL
1 stop22h 51m
Frontier
Thu 9/178:55 pm
BDL
- MKE
1 stop23h 20m
Frontier
Deal found 7/24![Frontier logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 pm
MKE
- ALB
1 stop4h 31m
American Airlines
Tue 8/256:30 pm
ALB
- MKE
1 stop5h 44m
American Airlines
Deal found 7/22![American Airlines logo]()
$303
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 25, 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 25, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:10 pm
MKE
- BOS
2 stops6h 10m
Southwest
Tue 9/159:10 am
BOS
- MKE
1 stop10h 25m
Southwest
Deal found 7/24![Southwest logo]()
$242
This JetBlue deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Mon 10/58:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 7/24![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Sun 8/235:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 7/21![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:47 pm
MKE
- BOS
1 stop4h 50m
United Airlines
Wed 9/1610:38 am
BOS
- MKE
1 stop5h 33m
United Airlines
Deal found 7/24![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:53 pm
MKE
- ALB
1 stop4h 33m
American Airlines
Mon 10/57:17 pm
ALB
- MKE
1 stop4h 57m
American Airlines
Deal found 7/24![American Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:30 am
MKE
- BOS
2 stops8h 00m
Southwest
Mon 11/165:20 am
BOS
- MKE
1 stop5h 25m
Southwest
Deal found 7/21![Southwest logo]()
$252
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/247:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/21![JetBlue logo]()
$297
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Fri 8/219:10 am
BOS
- MKE
Nonstop2h 41m
Delta
Deal found 7/20![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
MKE
- BOS
2 stops8h 55m
Southwest
Mon 8/315:00 am
BOS
- MKE
1 stop5h 35m
Southwest
Deal found 7/24![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:19 am
MKE
- BOS
2 stops6h 33m
United Airlines
Tue 8/186:00 pm
BOS
- MKE
1 stop6h 37m
United Airlines
Deal found 7/21![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/189:10 am
BOS
- MKE
Nonstop2h 41m
Delta
Deal found 7/24![Delta logo]()
$317
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Sun 10/188:45 am
BOS
- MKE
Nonstop2h 50m
JetBlue
Deal found 7/20![JetBlue logo]()
$317
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:25 pm
MKE
- BOS
2 stops8h 40m
Southwest
Mon 11/25:10 am
BOS
- MKE
1 stop5h 35m
Southwest
Deal found 7/21![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:30 am
MKE
- ALB
1 stop5h 34m
United Airlines
Sun 9/206:00 am
ALB
- MKE
1 stop5h 00m
United Airlines
Deal found 7/21![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:40 am
MKE
- ALB
2 stops8h 50m
Southwest
Tue 8/253:05 pm
ALB
- MKE
2 stops7h 20m
Southwest
Deal found 7/21![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:47 pm
MKE
- ALB
1 stop3h 34m
Delta
Mon 10/55:00 pm
ALB
- MKE
1 stop4h 05m
Delta
Deal found 7/22![Delta logo]()
$350
This FlightHub deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:55 am
MKE
- MVY
2 stops49h 38m
Multiple Airlines
Tue 9/294:48 pm
MVY
- MKE
1 stop18h 14m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$868
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Tue 9/226:00 am
BDL
- MKE
1 stop6h 30m
United Airlines
Deal found 7/21![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:45 am
MKE
- BDL
2 stops8h 25m
Southwest
Sat 9/265:50 am
BDL
- MKE
2 stops7h 50m
Southwest
Deal found 7/22![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:19 pm
MKE
- ALB
1 stop7h 17m
United Airlines
Sun 8/166:00 am
ALB
- MKE
1 stop5h 00m
United Airlines
Deal found 7/20![United Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:30 am
MKE
- BDL
1 stop6h 40m
Southwest
Wed 9/93:05 pm
BDL
- MKE
2 stops7h 15m
Southwest
Deal found 7/24![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:15 am
MKE
- BDL
2 stops6h 50m
United Airlines
Sun 8/309:40 am
BDL
- MKE
1 stop5h 53m
United Airlines
Deal found 7/20![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:00 am
MKE
- ALB
1 stop4h 15m
Southwest
Mon 10/127:20 am
ALB
- MKE
1 stop4h 25m
Southwest
Deal found 7/20![Southwest logo]()
$341
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:15 pm
MKE
- ALB
2 stops7h 43m
United Airlines
Sat 9/512:00 pm
ALB
- MKE
1 stop4h 47m
United Airlines
Deal found 7/20![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:45 am
MKE
- ALB
2 stops8h 00m
Southwest
Tue 8/253:05 pm
ALB
- MKE
2 stops7h 20m
Southwest
Deal found 7/20![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:15 am
MKE
- BDL
2 stops6h 50m
United Airlines
Sun 8/3010:33 am
BDL
- MKE
2 stops7h 47m
United Airlines
Deal found 7/20![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:45 am
MKE
- BDL
1 stop5h 15m
Southwest
Wed 8/263:05 pm
BDL
- MKE
2 stops7h 20m
Southwest
Deal found 7/20![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:20 am
MKE
- BDL
1 stop4h 20m
Southwest
Sun 10/185:40 am
BDL
- MKE
1 stop5h 45m
Southwest
Deal found 7/21![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:45 am
MKE
- BDL
2 stops7h 45m
Southwest
Mon 11/92:30 pm
BDL
- MKE
2 stops10h 25m
Southwest
Deal found 7/25![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:20 am
MKE
- ALB
1 stop5h 45m
Southwest
Mon 10/127:20 am
ALB
- MKE
1 stop4h 25m
Southwest
Deal found 7/21![Southwest logo]()
$371
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 25, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 8/197:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$225
This Super.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 8/187:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/25![JetBlue logo]()
$235
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Tue 8/186:00 pm
BOS
- MKE
1 stop5h 30m
Delta
Deal found 7/25![Delta logo]()
$247
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 8/187:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/23![JetBlue logo]()
$252
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:40 am
MKE
- ALB
1 stop3h 55m
Southwest
Tue 8/2512:50 pm
ALB
- MKE
2 stops8h 05m
Southwest
Deal found 7/21![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 pm
MKE
- ALB
1 stop4h 31m
American Airlines
Tue 8/256:30 pm
ALB
- MKE
1 stop5h 44m
American Airlines
Deal found 7/22![American Airlines logo]()
$303
This Cheapflightsfares deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares 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
Tue 9/17:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/21![JetBlue logo]()
$205
This CheapOair deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
Multiple Airlines
Mon 8/3110:04 am
BOS
- MKE
1 stop26h 09m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
MKE
- BOS
1 stop19h 59m
Frontier
Mon 8/3110:04 am
BOS
- MKE
1 stop26h 09m
Frontier
Deal found 7/20![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Tue 9/17:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/22![JetBlue logo]()
$215
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:47 pm
MKE
- BOS
1 stop6h 12m
Delta
Tue 9/19:10 am
BOS
- MKE
Nonstop2h 41m
Delta
Deal found 7/22![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:45 am
MKE
- BOS
1 stop4h 15m
Southwest
Tue 9/110:50 am
BOS
- MKE
2 stops10h 05m
Southwest
Deal found 7/21![Southwest logo]()
$232
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 25, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/20![JetBlue logo]()
$102
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/20![Delta logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/22![JetBlue logo]()
$107
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/22![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:40 am
MKE
- BOS
1 stop4h 35m
Southwest
Deal found 7/21![Southwest logo]()
$114
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
MKE
- BOS
1 stop5h 50m
United Airlines
Deal found 7/22![United Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:18 pm
MKE
- BOS
1 stop7h 29m
Delta
Deal found 7/24![Delta logo]()
$124
This Frontier deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:10 pm
MKE
- BOS
1 stop12h 59m
Frontier
Deal found 7/21![Frontier logo]()
$126
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:19 am
MKE
- BOS
1 stop5h 08m
United Airlines
Deal found 7/24![United Airlines logo]()
$129
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:45 am
MKE
- MVY
1 stop4h 53m
Delta
Deal found 7/20![Delta logo]()
$138
This Trip.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:10 pm
MKE
- BDL
1 stop22h 22m
Frontier
Deal found 7/20![Frontier logo]()
$146
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 pm
MKE
- ALB
1 stop4h 31m
American Airlines
Deal found 7/22![American Airlines logo]()
$152
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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (SmartFares) |
One-way from | $102 (Cheapflightsfares) |
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 25, 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 9/8
3:10 pm-10:20 pm
2 stops6h 10m
Boston Logan Intl
Tue 9/15
9:10 am-6:35 pm
1 stop10h 25m
$242
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 11/12
5:30 am-2:30 pm
2 stops8h 00m
Boston Logan Intl
Mon 11/16
5:20 am-9:45 am
1 stop5h 25m
$252
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 10/1
10:55 am-2:09 pm
Nonstop2h 14m
Boston Logan Intl
Mon 10/5
8:30 am-10:02 am
Nonstop2h 32m
$257
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/26
6:05 am-4:00 pm
2 stops8h 55m
Boston Logan Intl
Mon 8/31
5:00 am-9:35 am
1 stop5h 35m
$277
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 8/21
9:36 am-12:49 pm
Nonstop2h 13m
Boston Logan Intl
Mon 8/24
7:10 am-8:44 am
Nonstop2h 34m
$297
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 10/29
2:25 pm-12:05 am
2 stops8h 40m
Boston Logan Intl
Mon 11/2
5:10 am-9:45 am
1 stop5h 35m
$297
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 8/21
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Sun 8/23
5:30 am-8:55 am
1 stop4h 25m
$302
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 8/15
4:47 pm-11:59 pm
1 stop6h 12m
Boston Logan Intl
Fri 8/21
9:10 am-10:51 am
Nonstop2h 41m
$302
MilwaukeeAlbany
MKE - ALB
MKEALB
Milwaukee-Mitchell
Tue 8/18
7:40 am-5:30 pm
2 stops8h 50m
Albany Intl
Tue 8/25
3:05 pm-9:25 pm
2 stops7h 20m
$313
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 9/12
6:47 pm-12:37 am
1 stop4h 50m
Boston Logan Intl
Wed 9/16
10:38 am-3:11 pm
1 stop5h 33m
$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-MVY
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-MVY
MKE-BDL
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 25, 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 41% 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 25, 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 (1 on average).
How much does it cost to fly round-trip from Milwaukee to Massachusetts?
Airfare is below average for this route at the moment.
Milwaukee to Massachusetts flights typically cost between $230 and $380 in September.The cheapest round-trip price found within the last 5 days was $205 on JetBlue (Sep 15-Sep 19).
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 25, 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 25, 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.
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
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
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Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on July 25, 2026.
Popular flight searches
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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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$245 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$181 | Average$311 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$302 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$296 | FlexibilityNo cancel fee | On-time69% |