$80+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Apr 9 — Apr 161
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 March 10, 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 March 10, 2026.
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:08 pm
MKE
- BOS
1 stop6h 43m
Multiple Airlines
Tue 5/192:09 pm
BOS
- MKE
Nonstop2h 30m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$174
This Delta deal was found by Cheapflights users on 3/7. 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.
Wed 5/137:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Tue 6/24:25 pm
BOS
- MKE
Nonstop2h 43m
Delta
Deal found 3/7![Delta logo]()
$177
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:23 pm
MKE
- BOS
1 stop6h 08m
Multiple Airlines
Wed 5/62:09 pm
BOS
- MKE
Nonstop2h 30m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$179
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:13 pm
MKE
- BOS
1 stop7h 18m
Frontier
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Deal found 3/10![Frontier logo]()
$180
This Priceline deal was found by Cheapflights users on 3/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:08 pm
MKE
- BOS
1 stop6h 43m
Frontier
Fri 5/156:00 am
BOS
- MKE
1 stop11h 13m
Frontier
Deal found 3/5![Frontier logo]()
$181
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 5/137:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Sat 5/165:40 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 3/6![Delta logo]()
$187
This JetBlue deal was found by Cheapflights users on 3/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:09 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Wed 5/202:09 pm
BOS
- MKE
Nonstop2h 30m
JetBlue
Deal found 3/6![JetBlue logo]()
$192
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:34 pm
MKE
- BOS
Nonstop2h 15m
Multiple Airlines
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$194
This Frontier deal was found by Cheapflights users on 3/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:08 pm
MKE
- BOS
1 stop6h 43m
Frontier
Mon 5/256:00 am
BOS
- MKE
1 stop8h 34m
Frontier
Deal found 3/7![Frontier logo]()
$196
This United Airlines deal was found by Cheapflights users on 3/5. 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 4/47:41 pm
MKE
- BOS
1 stop4h 18m
United Airlines
Tue 4/76:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 3/5![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 3/5. 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.
Tue 5/56:38 pm
MKE
- BDL
1 stop3h 37m
Delta
Tue 5/127:05 am
BDL
- MKE
1 stop7h 41m
Delta
Deal found 3/5![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 3/6. 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.
Mon 5/45:05 pm
MKE
- ALB
1 stop5h 16m
Delta
Tue 5/512:23 pm
ALB
- MKE
1 stop4h 59m
Delta
Deal found 3/6![Delta logo]()
$322
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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/8. 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 5/132:45 pm
MKE
- BOS
1 stop6h 55m
Southwest
Wed 5/207:20 am
BOS
- MKE
1 stop4h 35m
Southwest
Deal found 3/8![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/6. 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 5/226:55 pm
MKE
- BOS
Nonstop2h 21m
Delta
Wed 5/274:25 pm
BOS
- MKE
Nonstop2h 43m
Delta
Deal found 3/6![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Tue 3/249:44 am
MKE
- BOS
2 stops6h 35m
United Airlines
Thu 3/266:00 am
BOS
- MKE
1 stop5h 30m
United Airlines
Deal found 3/9![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 5/275:01 pm
MKE
- BOS
1 stop5h 28m
Delta
Sat 5/305:40 am
BOS
- MKE
1 stop4h 09m
Delta
Deal found 3/6![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 3/8. 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 5/45:20 pm
MKE
- BOS
1 stop4h 50m
Southwest
Sat 5/96:00 am
BOS
- MKE
1 stop6h 50m
Southwest
Deal found 3/8![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/9. 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.
Sat 5/162:15 pm
MKE
- BOS
1 stop5h 50m
Southwest
Mon 5/255:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Deal found 3/9![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Thu 4/96:00 am
BOS
- MKE
2 stops8h 47m
United Airlines
Deal found 3/6![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 6/247:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Tue 6/305:30 am
BOS
- MKE
1 stop4h 11m
Delta
Deal found 3/6![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 9/37:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Tue 9/89:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Deal found 3/8![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/7. 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 6/166:05 am
MKE
- BOS
2 stops7h 38m
United Airlines
Sun 6/216:00 am
BOS
- MKE
1 stop6h 14m
United Airlines
Deal found 3/7![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/8. 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 5/17:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Mon 5/45:20 pm
BOS
- MKE
Nonstop2h 56m
Delta
Deal found 3/8![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 5/43:30 pm
MKE
- ALB
1 stop6h 45m
Southwest
Tue 5/54:20 pm
ALB
- MKE
1 stop6h 35m
Southwest
Deal found 3/6![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 3/7. 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 4/296:50 am
MKE
- BDL
1 stop6h 25m
United Airlines
Sat 5/212:40 pm
BDL
- MKE
1 stop5h 27m
United Airlines
Deal found 3/7![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 3/8. 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.
Mon 8/247:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Fri 8/285:05 pm
BOS
- MKE
Nonstop2h 52m
Delta
Deal found 3/8![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 3/7. 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 5/2812:40 pm
MKE
- ALB
1 stop8h 40m
Southwest
Sun 5/315:50 pm
ALB
- MKE
1 stop6h 55m
Southwest
Deal found 3/7![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Thu 5/217:30 am
MKE
- ALB
1 stop6h 56m
United Airlines
Thu 5/286:10 am
ALB
- MKE
1 stop4h 47m
United Airlines
Deal found 3/5![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 3/5. 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.
Wed 4/16:45 am
MKE
- BDL
1 stop4h 19m
Delta
Sat 4/45:34 am
BDL
- MKE
1 stop4h 12m
Delta
Deal found 3/5![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 3/267:18 pm
MKE
- ALB
1 stop4h 12m
United Airlines
Tue 3/316:00 am
ALB
- MKE
2 stops6h 32m
United Airlines
Deal found 3/9![United Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 3/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:30 pm
MKE
- ALB
1 stop6h 45m
Southwest
Thu 5/282:55 pm
ALB
- MKE
2 stops8h 55m
Southwest
Deal found 3/5![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 3/7. 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 5/512:33 pm
MKE
- BDL
1 stop6h 58m
Delta
Tue 5/126:00 am
BDL
- MKE
1 stop6h 23m
Delta
Deal found 3/7![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 3/7. 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.
Mon 5/46:56 pm
MKE
- ALB
1 stop4h 52m
United Airlines
Wed 5/64:55 pm
ALB
- MKE
1 stop6h 38m
United Airlines
Deal found 3/7![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 3/8. 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.
Thu 8/68:00 am
MKE
- ALB
2 stops8h 25m
Southwest
Mon 8/1010:15 am
ALB
- MKE
1 stop6h 45m
Southwest
Deal found 3/8![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Tue 5/56:49 am
MKE
- BDL
2 stops10h 53m
United Airlines
Tue 5/125:05 pm
BDL
- MKE
1 stop6h 25m
United Airlines
Deal found 3/9![United Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 3/9. 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.
Thu 7/25:50 am
MKE
- BDL
2 stops7h 20m
Southwest
Mon 7/612:40 pm
BDL
- MKE
2 stops10h 05m
Southwest
Deal found 3/9![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 8/65:55 am
MKE
- ALB
1 stop5h 06m
Delta
Mon 8/106:30 pm
ALB
- MKE
1 stop5h 55m
Delta
Deal found 3/8![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 3/6. 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.
Thu 5/212:55 pm
MKE
- BDL
1 stop6h 23m
Delta
Mon 5/256:00 am
BDL
- MKE
1 stop6h 20m
Delta
Deal found 3/6![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 3/5. 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.
Wed 6/105:25 pm
MKE
- BDL
1 stop5h 28m
Delta
Wed 6/177:00 am
BDL
- MKE
1 stop7h 44m
Delta
Deal found 3/5![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 3/6. 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.
Mon 6/87:00 am
MKE
- MVY
1 stop6h 19m
Delta
Sat 6/133:10 pm
MVY
- MKE
1 stop5h 59m
Delta
Deal found 3/6![Delta logo]()
$464
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated March 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/5. 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.
Fri 4/312:13 pm
MKE
- BOS
1 stop6h 28m
United Airlines
Tue 4/76:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 3/5![United Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/5. 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 4/47:41 pm
MKE
- BOS
1 stop4h 18m
United Airlines
Tue 4/76:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 3/5![United Airlines logo]()
$197
This Frontier deal was found by Cheapflights users on 3/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:32 pm
MKE
- BOS
1 stop7h 54m
Frontier
Mon 4/135:20 am
BOS
- MKE
1 stop11h 27m
Frontier
Deal found 3/8![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 3/8. 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 4/65:30 pm
MKE
- BOS
1 stop4h 40m
Southwest
Mon 4/137:25 pm
BOS
- MKE
2 stops14h 15m
Southwest
Deal found 3/8![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 3/7. 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 4/64:55 pm
MKE
- BOS
2 stops6h 50m
Southwest
Thu 4/95:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Deal found 3/7![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 3/8. 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.
Tue 4/75:50 am
MKE
- BOS
2 stops9h 05m
Southwest
Tue 4/142:25 pm
BOS
- MKE
2 stops9h 10m
Southwest
Deal found 3/8![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 3/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:00 am
MKE
- BOS
1 stop9h 25m
Southwest
Sun 4/266:10 am
BOS
- MKE
1 stop5h 35m
Southwest
Deal found 3/5![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Mon 4/275:25 pm
BOS
- MKE
2 stops7h 18m
United Airlines
Deal found 3/6![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 3/6. 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.
Wed 4/225:50 am
MKE
- BOS
1 stop4h 10m
Southwest
Mon 4/276:55 pm
BOS
- MKE
1 stop4h 20m
Southwest
Deal found 3/6![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/296:00 am
MKE
- BOS
1 stop5h 22m
Delta
Wed 4/295:20 pm
BOS
- MKE
Nonstop2h 56m
Delta
Deal found 3/9![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 4/306:49 am
MKE
- ALB
1 stop6h 14m
United Airlines
Mon 5/46:54 pm
ALB
- MKE
1 stop6h 05m
United Airlines
Deal found 3/9![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 3/9. 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.
Thu 4/304:50 pm
MKE
- ALB
1 stop3h 55m
Southwest
Mon 5/42:55 pm
ALB
- MKE
2 stops9h 05m
Southwest
Deal found 3/9![Southwest logo]()
$332
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 March 10, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Frontier deal was found by Cheapflights users on 3/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:08 pm
MKE
- BOS
1 stop6h 43m
Frontier
Deal found 3/5![Frontier logo]()
$80
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:34 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/9![JetBlue logo]()
$88
This Delta deal was found by Cheapflights users on 3/9. 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 5/47:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 3/9![Delta logo]()
$89
This Frontier deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:23 pm
MKE
- BOS
1 stop6h 08m
Frontier
Deal found 3/10![Frontier logo]()
$90
This CheapOair deal was found by Cheapflights users on 3/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:33 am
MKE
- BOS
1 stop23h 58m
Frontier
Deal found 3/5![Frontier logo]()
$92
This Delta deal was found by Cheapflights users on 3/8. 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 5/912:40 pm
MKE
- BOS
1 stop5h 18m
Delta
Deal found 3/8![Delta logo]()
$99
This Frontier deal was found by Cheapflights users on 3/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:34 pm
MKE
- BOS
1 stop8h 28m
Frontier
Deal found 3/6![Frontier logo]()
$101
This JetBlue deal was found by Cheapflights users on 3/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:34 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/6![JetBlue logo]()
$104
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:00 pm
MKE
- BOS
1 stop5h 29m
Delta
Deal found 3/10![Delta logo]()
$109
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 3/6![United Airlines logo]()
$114
This Frontier deal was found by Cheapflights users on 3/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:32 pm
MKE
- BOS
1 stop7h 54m
Frontier
Deal found 3/6![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 3/5. 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.
Fri 6/58:26 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 3/5![JetBlue logo]()
$117
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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (CheapOair) |
One-way from | $80 (Frontier) |
Popular in | February |
Cheapest in | September |
Average price | $368 |
Good round-trip deal | $227 or less |
Good one-way deal | $108 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 March 10, 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
Wed 5/13
2:45 pm-10:40 pm
1 stop6h 55m
Boston Logan Intl
Wed 5/20
7:20 am-10:55 am
1 stop4h 35m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/22
6:55 pm-10:16 pm
Nonstop2h 21m
Boston Logan Intl
Wed 5/27
4:25 pm-6:08 pm
Nonstop2h 43m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 5/27
5:01 pm-11:29 pm
1 stop5h 28m
Boston Logan Intl
Sat 5/30
5:40 am-8:49 am
1 stop4h 09m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 5/4
5:20 pm-11:10 pm
1 stop4h 50m
Boston Logan Intl
Sat 5/9
6:00 am-11:50 am
1 stop6h 50m
$197
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 5/16
2:15 pm-9:05 pm
1 stop5h 50m
Boston Logan Intl
Mon 5/25
5:40 am-9:50 am
1 stop5h 10m
$247
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 6/24
7:35 pm-10:54 pm
Nonstop2h 19m
Boston Logan Intl
Tue 6/30
5:30 am-8:41 am
1 stop4h 11m
$262
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 3/24
9:44 am-5:19 pm
2 stops6h 35m
Boston Logan Intl
Thu 3/26
6:00 am-10:30 am
1 stop5h 30m
$282
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 9/3
7:35 pm-10:54 pm
Nonstop2h 19m
Boston Logan Intl
Tue 9/8
9:00 am-10:44 am
Nonstop2h 44m
$282
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/1
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Mon 5/4
5:20 pm-7:16 pm
Nonstop2h 56m
$282
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sun 4/5
5:10 am-11:01 am
1 stop4h 51m
Boston Logan Intl
Thu 4/9
6:00 am-1:47 pm
2 stops8h 47m
$287
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-ALB
MKE-BDL
MKE-MVY
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Massachusetts
MKE-USMA
MKE-BOS
MKE-ALB
MKE-BDL
MKE-MVY
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $91). Flying from Milwaukee to Massachusetts in January is currently the most expensive (average of $117). 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 March 10, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 45% on your trip compared to booking a flight at noon.
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 February 21, 2026.
Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Saturday afternoons 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 March 10, 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
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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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 March 10, 2026.
Popular flight searches
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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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$104 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$258 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$282 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$192 | Average$312 | FlexibilityNo cancel fee | On-time69% |