$96+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 8 — Aug 151
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 9, 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 9, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/2610:19 am
MKE
- BOS
1 stop5h 08m
United Airlines
Wed 9/27:00 pm
BOS
- MKE
1 stop5h 37m
United Airlines
Deal found 7/8![United Airlines logo]()
$179
This SmartFares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 9/2210:30 am
MKE
- BOS
1 stop4h 57m
United Airlines
Sat 9/265:45 am
BOS
- MKE
2 stops6h 45m
United Airlines
Deal found 7/7![United Airlines logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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
Sat 8/297:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/6![JetBlue logo]()
$189
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
Wed 9/21:05 pm
BOS
- MKE
1 stop7h 50m
Southwest
Deal found 7/8![Southwest logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/8![JetBlue logo]()
$195
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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
1 stop5h 35m
United Airlines
Sat 8/156:54 pm
BOS
- MKE
1 stop5h 43m
United Airlines
Deal found 7/7![United Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/257:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Wed 7/296:05 am
BOS
- MKE
1 stop5h 06m
United Airlines
Deal found 7/5![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 7/7![Southwest logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/29:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 9/77:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
Deal found 7/5![JetBlue logo]()
$199
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/54:25 pm
MKE
- BOS
1 stop4h 50m
Southwest
Wed 8/123:20 pm
BOS
- MKE
1 stop7h 05m
Southwest
Deal found 7/8![Southwest logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/8![JetBlue logo]()
$205
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/196:50 pm
MKE
- BOS
1 stop4h 15m
Southwest
Sat 10/245:35 am
BOS
- MKE
1 stop7h 45m
Southwest
Deal found 7/8![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sat 9/261:00 pm
BOS
- MKE
1 stop6h 17m
Delta
Deal found 7/4![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 11/57:50 am
MKE
- BOS
1 stop7h 31m
United Airlines
Mon 11/95:45 am
BOS
- MKE
2 stops6h 43m
United Airlines
Deal found 7/8![United Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/126:20 am
MKE
- MVY
1 stop7h 10m
American Airlines
Tue 8/185:25 pm
MVY
- MKE
1 stop7h 34m
American Airlines
Deal found 7/8![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/178:00 am
MKE
- BOS
2 stops8h 50m
Southwest
Thu 8/203:35 pm
BOS
- MKE
1 stop6h 05m
Southwest
Deal found 7/7![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 9/216:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Fri 9/254:15 pm
BOS
- MKE
Nonstop2h 37m
Delta
Deal found 7/9![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/185:47 pm
MKE
- BOS
1 stop4h 30m
Delta
Tue 9/225:40 am
BOS
- MKE
1 stop4h 12m
Delta
Deal found 7/5![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:35 am
MKE
- BOS
2 stops7h 55m
Southwest
Sat 8/155:50 am
BOS
- MKE
2 stops7h 50m
Southwest
Deal found 7/7![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/46:20 am
MKE
- BOS
2 stops10h 04m
United Airlines
Tue 8/115:45 am
BOS
- MKE
2 stops7h 53m
United Airlines
Deal found 7/8![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 9/101:55 pm
MKE
- ALB
1 stop6h 45m
Southwest
Tue 9/153:05 pm
ALB
- MKE
2 stops7h 20m
Southwest
Deal found 7/6![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/284:47 pm
MKE
- BDL
1 stop6h 04m
Delta
Tue 9/112:55 pm
BDL
- MKE
1 stop6h 13m
Delta
Deal found 7/7![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/285:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Tue 9/16:00 am
BDL
- MKE
1 stop5h 00m
United Airlines
Deal found 7/7![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/276:25 am
MKE
- BDL
1 stop5h 35m
Southwest
Tue 9/17:45 am
BDL
- MKE
1 stop4h 20m
Southwest
Deal found 7/7![Southwest logo]()
$264
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 11/63:00 pm
MKE
- BDL
2 stops7h 59m
United Airlines
Sat 11/74:56 pm
BDL
- MKE
1 stop4h 59m
United Airlines
Deal found 7/9![United Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/45:00 am
MKE
- BDL
1 stop4h 38m
United Airlines
Tue 9/810:33 am
BDL
- MKE
2 stops7h 57m
United Airlines
Deal found 7/8![United Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 11/64:50 pm
MKE
- BDL
1 stop4h 20m
Southwest
Mon 11/94:25 pm
BDL
- MKE
1 stop8h 20m
Southwest
Deal found 7/7![Southwest logo]()
$300
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/711:31 am
MKE
- BOS
Nonstop2h 28m
Delta
Mon 8/105:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 7/7![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:50 pm
MKE
- ALB
1 stop5h 12m
United Airlines
Sat 12/124:30 pm
ALB
- MKE
1 stop7h 09m
United Airlines
Deal found 7/7![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 11/66:10 am
MKE
- BDL
2 stops15h 00m
Southwest
Sat 11/77:40 am
BDL
- MKE
2 stops9h 30m
Southwest
Deal found 7/9![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/15:47 pm
MKE
- ALB
1 stop4h 12m
Delta
Mon 10/56:00 am
ALB
- MKE
1 stop3h 52m
Delta
Deal found 7/7![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 11/66:18 pm
MKE
- BOS
1 stop5h 48m
United Airlines
Mon 11/95:45 am
BOS
- MKE
2 stops6h 43m
United Airlines
Deal found 7/7![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 11/66:55 am
MKE
- BDL
1 stop4h 10m
Southwest
Fri 11/66:40 pm
BDL
- MKE
1 stop4h 35m
Southwest
Deal found 7/9![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 7/4![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 9/117:14 am
MKE
- ALB
1 stop3h 47m
Delta
Tue 9/151:15 pm
ALB
- MKE
1 stop3h 50m
Delta
Deal found 7/6![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/45:45 am
MKE
- BDL
2 stops8h 20m
Southwest
Tue 9/812:45 pm
BDL
- MKE
2 stops8h 10m
Southwest
Deal found 7/8![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 10/302:25 pm
MKE
- ALB
1 stop7h 55m
Southwest
Sun 11/18:35 am
ALB
- MKE
1 stop9h 55m
Southwest
Deal found 7/7![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/215:00 pm
MKE
- ALB
1 stop4h 15m
Southwest
Mon 8/246:05 pm
ALB
- MKE
1 stop4h 20m
Southwest
Deal found 7/6![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 7/266:45 am
MKE
- MVY
1 stop4h 53m
Delta
Wed 7/293:43 pm
MVY
- MKE
1 stop7h 47m
Delta
Deal found 7/7![Delta logo]()
$690
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 9, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated July 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 7/257:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Wed 7/296:05 am
BOS
- MKE
1 stop5h 06m
United Airlines
Deal found 7/5![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/54:25 pm
MKE
- BOS
1 stop4h 50m
Southwest
Wed 8/123:20 pm
BOS
- MKE
1 stop7h 05m
Southwest
Deal found 7/8![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/74:50 pm
MKE
- BOS
1 stop4h 40m
Southwest
Mon 8/175:00 am
BOS
- MKE
1 stop5h 35m
Southwest
Deal found 7/9![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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
1 stop5h 35m
United Airlines
Sat 8/156:54 pm
BOS
- MKE
1 stop5h 43m
United Airlines
Deal found 7/7![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/255:54 pm
MKE
- ALB
1 stop4h 23m
Delta
Tue 9/15:45 am
ALB
- MKE
1 stop5h 17m
Delta
Deal found 7/7![Delta logo]()
$249
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/2610:19 am
MKE
- BOS
1 stop5h 08m
United Airlines
Wed 9/27:00 pm
BOS
- MKE
1 stop5h 37m
United Airlines
Deal found 7/8![United Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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
Sat 8/297:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/6![JetBlue logo]()
$189
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/269:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Wed 9/27:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/8![JetBlue logo]()
$195
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 7/7![Southwest logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$199
This SmartFares deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/299:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Mon 8/317:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
Wed 9/21:05 pm
BOS
- MKE
1 stop7h 50m
Southwest
Deal found 7/8![Southwest logo]()
$192
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 9, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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 8/105:45 am
MKE
- BOS
1 stop4h 55m
Southwest
Deal found 7/7![Southwest logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/8![JetBlue logo]()
$97
This American Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/41:15 pm
MKE
- BOS
1 stop6h 45m
American Airlines
Deal found 7/4![American Airlines logo]()
$98
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
Deal found 7/8![Delta logo]()
$99
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:00 am
MKE
- BOS
2 stops6h 47m
United Airlines
Deal found 7/5![United Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Mon 9/2811:25 am
MKE
- BOS
Nonstop2h 39m
JetBlue
Deal found 7/6![JetBlue logo]()
$107
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:29 pm
MKE
- BOS
1 stop6h 45m
United Airlines
Deal found 7/8![United Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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
2 stops8h 20m
Southwest
Deal found 7/9![Southwest logo]()
$111
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Mon 7/209:35 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/5![JetBlue logo]()
$112
This United Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/37:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 7/5![United Airlines logo]()
$116
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 10/95:55 pm
MKE
- BOS
1 stop4h 25m
Delta
Deal found 7/8![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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
- BDL
1 stop6h 04m
Delta
Deal found 7/8![Delta logo]()
$132
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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $179 (United Airlines) |
One-way from | $96 (Southwest) |
Popular in | February |
Cheapest in | May |
Average price | $304 |
Good round-trip deal | $217 or less |
Good one-way deal | $128 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 9, 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
Mon 10/19
6:50 pm-12:05 am
1 stop4h 15m
Boston Logan Intl
Sat 10/24
5:35 am-12:20 pm
1 stop7h 45m
$198
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 9/23
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Sat 9/26
1:00 pm-6:17 pm
1 stop6h 17m
$207
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 8/17
8:00 am-5:50 pm
2 stops8h 50m
Boston Logan Intl
Thu 8/20
3:35 pm-8:40 pm
1 stop6h 05m
$210
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 9/21
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Fri 9/25
4:15 pm-5:52 pm
Nonstop2h 37m
$217
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 9/18
5:47 pm-11:17 pm
1 stop4h 30m
Boston Logan Intl
Tue 9/22
5:40 am-8:52 am
1 stop4h 12m
$227
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 8/13
5:35 am-2:30 pm
2 stops7h 55m
Boston Logan Intl
Sat 8/15
5:50 am-12:40 pm
2 stops7h 50m
$239
MilwaukeeAlbany
MKE - ALB
MKEALB
Milwaukee-Mitchell
Thu 9/10
1:55 pm-9:40 pm
1 stop6h 45m
Albany Intl
Tue 9/15
3:05 pm-9:25 pm
2 stops7h 20m
$256
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Fri 8/28
4:47 pm-11:51 pm
1 stop6h 04m
Hartford Bradley Intl
Tue 9/1
12:55 pm-6:08 pm
1 stop6h 13m
$263
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 11/5
7:50 am-4:21 pm
1 stop7h 31m
Boston Logan Intl
Mon 11/9
5:45 am-11:28 am
2 stops6h 43m
$264
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Thu 8/27
6:25 am-1:00 pm
1 stop5h 35m
Hartford Bradley Intl
Tue 9/1
7:45 am-11:05 am
1 stop4h 20m
$264
Showing 1-10 of 58 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-BDL
MKE-MVY
MKE-ALB
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-BDL
MKE-MVY
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 $65). 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 July 9, 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.
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 4, 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 9, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
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
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Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on July 9, 2026.
Popular flight searches
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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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$168 | Average$301 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$297 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$305 | FlexibilityNo cancel fee | On-time71% |