$58+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Apr 25 — May 21
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 26, 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 26, 2026.
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:11 am
MKE
- BOS
1 stop7h 34m
American Airlines
Mon 4/135:40 pm
BOS
- MKE
1 stop6h 17m
American Airlines
Deal found 3/25![American Airlines logo]()
$159
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/307:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Sun 5/35:30 am
BOS
- MKE
1 stop4h 20m
Delta
Deal found 3/26![Delta logo]()
$162
This Southwest deal was found by Cheapflights users on 3/25. 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 5/2912:40 pm
MKE
- BOS
2 stops10h 15m
Southwest
Mon 6/17:25 pm
BOS
- MKE
1 stop4h 45m
Southwest
Deal found 3/25![Southwest logo]()
$164
This KAYAK deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Mon 5/42:25 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/26![JetBlue logo]()
$167
This Southwest deal was found by Cheapflights users on 3/25. 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 5/15:20 pm
MKE
- BOS
1 stop4h 50m
Southwest
Mon 5/47:25 pm
BOS
- MKE
1 stop4h 45m
Southwest
Deal found 3/25![Southwest logo]()
$172
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:37 pm
MKE
- BOS
1 stop5h 48m
American Airlines
Tue 5/199:05 am
BOS
- MKE
1 stop8h 34m
American Airlines
Deal found 3/25![American Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 3/24. 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 4/214:40 pm
MKE
- BOS
1 stop4h 40m
Southwest
Tue 4/286:20 pm
BOS
- MKE
1 stop4h 25m
Southwest
Deal found 3/24![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:40 am
MKE
- BOS
1 stop4h 20m
Southwest
Wed 5/136:20 pm
BOS
- MKE
1 stop4h 25m
Southwest
Deal found 3/23![Southwest logo]()
$176
This Delta deal was found by Cheapflights users on 3/24. 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 4/296:38 pm
MKE
- BOS
1 stop4h 14m
Delta
Mon 5/43:00 pm
BOS
- MKE
1 stop7h 30m
Delta
Deal found 3/24![Delta logo]()
$177
This Frontier deal was found by Cheapflights users on 3/25. 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 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 3/25![Frontier logo]()
$181
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:00 am
MKE
- ALB
1 stop4h 43m
United Airlines
Tue 6/26:46 pm
ALB
- MKE
1 stop4h 38m
United Airlines
Deal found 3/25![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 5/59:35 am
MKE
- BDL
1 stop5h 56m
Delta
Tue 5/124:59 pm
BDL
- MKE
1 stop4h 29m
Delta
Deal found 3/25![Delta logo]()
$263
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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 3/21. 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 5/17:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Wed 5/135:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Deal found 3/21![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 3/25. 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.
Wed 4/225:50 am
MKE
- BDL
1 stop3h 50m
Southwest
Wed 4/293:15 pm
BDL
- MKE
2 stops7h 30m
Southwest
Deal found 3/25![Southwest logo]()
$268
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:11 am
MKE
- ALB
1 stop4h 26m
American Airlines
Wed 4/296:26 am
ALB
- MKE
1 stop5h 17m
American Airlines
Deal found 3/25![American Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:13 pm
MKE
- BOS
2 stops7h 41m
United Airlines
Sat 4/2510:05 am
BOS
- MKE
2 stops12h 18m
United Airlines
Deal found 3/25![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 3/21. 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 5/17:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Tue 5/51:06 pm
BOS
- MKE
1 stop5h 52m
Delta
Deal found 3/21![Delta logo]()
$182
This Delta deal was found by Cheapflights users on 3/21. 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 5/17:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Mon 5/45:30 am
BOS
- MKE
1 stop4h 20m
Delta
Deal found 3/21![Delta logo]()
$182
This Delta deal was found by Cheapflights users on 3/25. 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 6/105:56 pm
MKE
- BOS
1 stop4h 31m
Delta
Tue 6/165:30 am
BOS
- MKE
1 stop4h 21m
Delta
Deal found 3/25![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 3/21. 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 4/305:50 am
MKE
- BOS
1 stop4h 05m
Southwest
Mon 5/47:25 pm
BOS
- MKE
2 stops14h 15m
Southwest
Deal found 3/21![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:50 am
MKE
- BOS
2 stops7h 00m
Southwest
Wed 5/202:25 pm
BOS
- MKE
2 stops9h 10m
Southwest
Deal found 3/23![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 9/155:00 pm
MKE
- BOS
1 stop5h 32m
Delta
Tue 9/229:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Deal found 3/25![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:37 am
MKE
- ALB
1 stop4h 27m
United Airlines
Wed 5/69:20 am
ALB
- MKE
1 stop4h 51m
United Airlines
Deal found 3/23![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:40 am
MKE
- ALB
1 stop11h 05m
Southwest
Tue 5/126:40 pm
ALB
- MKE
1 stop4h 05m
Southwest
Deal found 3/23![Southwest logo]()
$283
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Tue 5/51:46 pm
MKE
- BDL
1 stop6h 39m
United Airlines
Wed 5/66:00 am
BDL
- MKE
1 stop4h 45m
United Airlines
Deal found 3/24![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 3/24. 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 8/46:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Tue 8/112:00 pm
BOS
- MKE
1 stop7h 52m
Delta
Deal found 3/24![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 3/24. 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 5/55:05 pm
MKE
- BDL
1 stop5h 10m
Delta
Tue 5/125:30 am
BDL
- MKE
1 stop4h 19m
Delta
Deal found 3/24![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 4/88:00 am
MKE
- BOS
2 stops7h 05m
Southwest
Thu 4/165:30 am
BOS
- MKE
2 stops7h 30m
Southwest
Deal found 3/22![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Thu 7/21:30 pm
MKE
- BDL
2 stops9h 29m
United Airlines
Sun 7/56:09 am
BDL
- MKE
1 stop4h 49m
United Airlines
Deal found 3/24![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 3/25. 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 8/56:00 am
MKE
- BOS
1 stop6h 21m
Delta
Thu 8/65:40 am
BOS
- MKE
1 stop4h 10m
Delta
Deal found 3/25![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 3/21. 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 4/305:50 am
MKE
- BDL
1 stop3h 50m
Southwest
Tue 5/511:20 am
BDL
- MKE
2 stops8h 40m
Southwest
Deal found 3/21![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/285:00 am
MKE
- BDL
2 stops8h 06m
United Airlines
Thu 5/286:36 pm
BDL
- MKE
1 stop4h 48m
United Airlines
Deal found 3/26![United Airlines logo]()
$429
This Travelocity deal was found by Cheapflights users on 3/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:41 am
MKE
- PVC
1 stop5h 04m
Multiple Airlines
Tue 7/147:00 am
PVC
- MKE
2 stops17h 59m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$1,355
This Delta deal was found by Cheapflights users on 3/21. 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.
Thu 4/306:50 am
MKE
- BDL
1 stop4h 07m
Delta
Tue 5/56:00 am
BDL
- MKE
1 stop6h 27m
Delta
Deal found 3/21![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/102:40 pm
MKE
- ALB
1 stop7h 20m
Delta
Tue 4/145:50 am
ALB
- MKE
1 stop5h 30m
Delta
Deal found 3/26![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 3/22. 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 9/122:45 pm
MKE
- ALB
1 stop7h 53m
Delta
Sat 9/196:00 am
ALB
- MKE
1 stop3h 41m
Delta
Deal found 3/22![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:00 am
MKE
- ALB
1 stop5h 47m
Delta
Sun 7/125:45 am
ALB
- MKE
1 stop5h 22m
Delta
Deal found 3/23![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 3/24. 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 6/107:00 am
MKE
- MVY
1 stop4h 38m
Delta
Thu 6/1811:42 am
MVY
- MKE
1 stop6h 34m
Delta
Deal found 3/24![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 3/24. 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 6/97:00 am
MKE
- MVY
1 stop4h 38m
Delta
Thu 6/1811:42 am
MVY
- MKE
1 stop6h 34m
Delta
Deal found 3/24![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 6/127:00 am
MKE
- MVY
1 stop4h 38m
Delta
Mon 6/1511:42 am
MVY
- MKE
1 stop6h 34m
Delta
Deal found 3/26![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
MKE
- MVY
1 stop4h 24m
Delta
Tue 6/212:04 pm
MVY
- MKE
1 stop6h 00m
Delta
Deal found 3/23![Delta logo]()
$727
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated March 26, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:50 am
MKE
- BOS
2 stops6h 52m
United Airlines
Thu 4/96:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 3/23![United Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:50 am
MKE
- BOS
2 stops6h 52m
United Airlines
Wed 4/226:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 3/25![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 3/21. 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 4/85:50 am
MKE
- BOS
2 stops9h 05m
Southwest
Mon 4/137:25 pm
BOS
- MKE
2 stops14h 15m
Southwest
Deal found 3/21![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:11 am
MKE
- BOS
1 stop7h 34m
American Airlines
Mon 4/135:40 pm
BOS
- MKE
1 stop6h 17m
American Airlines
Deal found 3/25![American Airlines logo]()
$159
This Southwest deal was found by Cheapflights users on 3/24. 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 4/214:40 pm
MKE
- BOS
1 stop4h 40m
Southwest
Tue 4/286:20 pm
BOS
- MKE
1 stop4h 25m
Southwest
Deal found 3/24![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 3/25. 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.
Wed 4/225:50 am
MKE
- BDL
1 stop3h 50m
Southwest
Wed 4/294:05 pm
BDL
- MKE
1 stop6h 50m
Southwest
Deal found 3/25![Southwest logo]()
$263
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:11 am
MKE
- ALB
1 stop4h 26m
American Airlines
Wed 4/296:26 am
ALB
- MKE
1 stop5h 17m
American Airlines
Deal found 3/25![American Airlines logo]()
$277
This KAYAK deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Mon 5/42:25 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/26![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 3/24. 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 4/296:38 pm
MKE
- BOS
1 stop4h 14m
Delta
Mon 5/43:00 pm
BOS
- MKE
1 stop7h 30m
Delta
Deal found 3/24![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/307:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Sun 5/35:30 am
BOS
- MKE
1 stop4h 20m
Delta
Deal found 3/26![Delta logo]()
$162
This SmartFares deal was found by Cheapflights users on 3/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Mon 5/42:25 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/22![JetBlue logo]()
$181
This United Airlines deal was found by Cheapflights users on 3/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:10 pm
MKE
- BOS
1 stop4h 49m
United Airlines
Wed 5/68:05 am
BOS
- MKE
1 stop6h 06m
United Airlines
Deal found 3/25![United Airlines logo]()
$187
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 26, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 26, 2026.
This Super.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/26![JetBlue logo]()
$58
This KAYAK deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:35 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/26![JetBlue logo]()
$59
This Delta deal was found by Cheapflights users on 3/25. 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.
Tue 5/57:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 3/25![Delta logo]()
$69
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:13 pm
MKE
- BOS
1 stop7h 18m
Frontier
Deal found 3/25![Frontier logo]()
$70
This KAYAK deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:56 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/26![JetBlue logo]()
$74
This Expedia deal was found by Cheapflights users on 3/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 3/24![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 3/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:58 pm
MKE
- BOS
Nonstop2h 17m
JetBlue
Deal found 3/23![JetBlue logo]()
$78
This JetBlue deal was found by Cheapflights users on 3/23. 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.
Tue 5/194:58 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/23![JetBlue logo]()
$79
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:40 pm
MKE
- BOS
1 stop4h 45m
American Airlines
Deal found 3/25![American Airlines logo]()
$80
This Southwest deal was found by Cheapflights users on 3/25. 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 5/15:20 pm
MKE
- BOS
1 stop4h 50m
Southwest
Deal found 3/25![Southwest logo]()
$84
This Expedia deal was found by Cheapflights users on 3/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:41 am
MKE
- BOS
Nonstop2h 19m
JetBlue
Deal found 3/24![JetBlue logo]()
$86
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:15 am
MKE
- BOS
1 stop7h 00m
Southwest
Deal found 3/23![Southwest logo]()
$87
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 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (American Airlines) |
One-way from | $58 (Super.com) |
Popular in | February |
Cheapest in | September |
Average price | $368 |
Good round-trip deal | $226 or less |
Good one-way deal | $158 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 26, 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
Quickest round-trip
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/1
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Wed 5/13
5:20 pm-7:08 pm
Nonstop2h 48m
$172
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/1
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Tue 5/5
1:06 pm-5:58 pm
1 stop5h 52m
$182
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 5/1
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Mon 5/4
5:30 am-8:50 am
1 stop4h 20m
$182
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 6/10
5:56 pm-11:27 pm
1 stop4h 31m
Boston Logan Intl
Tue 6/16
5:30 am-8:51 am
1 stop4h 21m
$202
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 9/15
5:00 pm-11:32 pm
1 stop5h 32m
Boston Logan Intl
Tue 9/22
9:00 am-10:44 am
Nonstop2h 44m
$247
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 8/4
6:59 pm-10:26 pm
Nonstop2h 27m
Boston Logan Intl
Tue 8/11
2:00 pm-8:52 pm
1 stop7h 52m
$262
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Tue 5/5
5:05 pm-11:15 pm
1 stop5h 10m
Hartford Bradley Intl
Tue 5/12
5:30 am-8:49 am
1 stop4h 19m
$263
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Wed 4/22
5:50 am-10:40 am
1 stop3h 50m
Hartford Bradley Intl
Wed 4/29
3:15 pm-9:45 pm
2 stops7h 30m
$268
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 4/30
5:50 am-10:55 am
1 stop4h 05m
Boston Logan Intl
Mon 5/4
7:25 pm-8:40 am
2 stops14h 15m
$272
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 5/12
5:50 am-1:50 pm
2 stops7h 00m
Boston Logan Intl
Wed 5/20
2:25 pm-10:35 pm
2 stops9h 10m
$275
Showing 1-10 of 57 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-ALB
MKE-MVY
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-BDL
MKE-ALB
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 26, 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 43% 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 March 23, 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.
How much does it cost to fly round-trip from Milwaukee to Massachusetts?
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 26, 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
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Massachusetts
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Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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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 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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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 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$105 | Average$354 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$263 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$178 | Average$282 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$321 | FlexibilityNo cancel fee | On-time69% |