$126+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 August 25, 2026.
Explore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am -
Nonstop2h 14m
Sat 9/198:30 am -
Nonstop2h 32m
Deal found 8/24![JetBlue logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:55 am -
Nonstop2h 14m
Sat 9/268:30 am -
Nonstop2h 32m
Deal found 8/19![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 8/21. 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.
Wed 9/1611:35 am -
Nonstop2h 33m
Sat 9/1912:15 pm -
Nonstop2h 35m
Deal found 8/21![Delta logo]()
$257
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:15 am -
1 stop23h 47m
Thu 11/510:11 am -
1 stop9h 57m
Deal found 8/19![Frontier logo]()
$258
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 pm -
Nonstop2h 31m
Sat 9/269:10 am -
1 stop4h 38m
Deal found 8/19![Delta logo]()
$267
This CheapOair deal was found by Cheapflights users on 8/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:15 am -
1 stop23h 47m
Sat 10/2411:47 am -
1 stop22h 33m
Deal found 8/24![Frontier logo]()
$268
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am -
Nonstop2h 14m
Thu 9/178:30 am -
Nonstop2h 32m
Deal found 8/24![JetBlue logo]()
$273
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:36 am -
Nonstop2h 13m
Tue 9/87:10 am -
Nonstop2h 34m
Deal found 8/23![JetBlue logo]()
$275
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am -
1 stop6h 06m
Sat 9/197:05 am -
1 stop5h 25m
Deal found 8/24![United Airlines logo]()
$277
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:55 am -
Nonstop2h 14m
Tue 9/158:30 am -
Nonstop2h 32m
Deal found 8/24![JetBlue logo]()
$280
This Super.com deal was found by Cheapflights users on 8/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:25 am -
Nonstop2h 39m
Tue 10/138:45 am -
Nonstop2h 50m
Deal found 8/21![JetBlue logo]()
$281
This Delta deal was found by Cheapflights users on 8/24. 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 9/166:00 am -
1 stop4h 49m
Sat 9/196:35 am -
1 stop6h 02m
Deal found 8/24![Delta logo]()
$309
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 August 25, 2026.
Discover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:05 pm -
1 stop4h 32m
Tue 10/205:45 am -
2 stops6h 45m
Deal found 8/24![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 8/24. 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.
Fri 9/116:35 pm -
Nonstop2h 31m
Tue 9/157:00 am -
1 stop6h 43m
Deal found 8/24![Delta logo]()
$292
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am -
1 stop7h 36m
Wed 9/233:06 pm -
1 stop7h 48m
Deal found 8/20![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 8/24. 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.
Mon 9/216:25 am -
1 stop7h 05m
Mon 9/285:00 am -
1 stop5h 35m
Deal found 8/24![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 8/22. 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.
Wed 10/1410:36 am -
1 stop4h 54m
Sun 10/189:07 am -
Nonstop2h 46m
Deal found 8/22![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/24. 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 10/155:00 am -
1 stop4h 39m
Sat 10/176:03 am -
2 stops8h 40m
Deal found 8/24![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 8/24. 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 9/166:00 am -
1 stop4h 49m
Sat 9/196:35 am -
1 stop6h 02m
Deal found 8/24![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:00 pm -
1 stop4h 10m
Fri 10/307:05 pm -
1 stop6h 30m
Deal found 8/21![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:15 pm -
1 stop5h 27m
Thu 9/104:50 pm -
1 stop6h 46m
Deal found 8/22![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/24. 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.
Thu 10/152:25 pm -
2 stops8h 25m
Sat 10/1712:55 pm -
2 stops8h 05m
Deal found 8/24![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 8/24. 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 9/152:20 pm -
2 stops8h 39m
Mon 9/216:00 am -
1 stop5h 00m
Deal found 8/24![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 8/24. 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.
Thu 10/156:49 pm -
1 stop3h 38m
Sun 10/186:00 am -
1 stop3h 39m
Deal found 8/24![Delta logo]()
$353
This Southwest deal was found by Cheapflights users on 8/24. 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.
Fri 10/164:35 pm -
2 stops6h 30m
Mon 10/197:50 pm -
1 stop4h 55m
Deal found 8/24![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:03 pm -
1 stop5h 15m
Fri 10/305:02 pm -
1 stop6h 13m
Deal found 8/21![United Airlines logo]()
$345
This KAYAK deal was found by Cheapflights users on 8/22. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:55 am -
1 stop8h 13m
Mon 9/284:20 pm -
1 stop18h 42m
Deal found 8/22![Multiple Airlines logo]()
$974
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am -
2 stops7h 50m
Sat 10/38:10 am -
2 stops7h 50m
Deal found 8/24![Southwest logo]()
$375
This Delta deal was found by Cheapflights users on 8/23. 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.
Sun 10/1111:33 am -
Nonstop2h 29m
Sun 10/185:39 am -
1 stop4h 00m
Deal found 8/23![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:18 am -
1 stop5h 49m
Sat 10/2412:45 pm -
1 stop7h 25m
Deal found 8/22![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:45 am -
2 stops8h 25m
Mon 1/1812:30 pm -
1 stop10h 00m
Deal found 8/21![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
1 stop4h 38m
Thu 10/19:36 am -
1 stop4h 12m
Deal found 8/20![Delta logo]()
$393
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:42 am -
1 stop4h 39m
Wed 10/75:45 am -
2 stops6h 45m
Deal found 8/21![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 8/22. 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.
Fri 10/162:25 pm -
2 stops8h 25m
Sat 10/171:10 pm -
2 stops7h 50m
Deal found 8/22![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:52 pm -
2 stops7h 07m
Sat 10/176:00 am -
1 stop6h 30m
Deal found 8/22![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 8/22. 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.
Sun 9/67:00 am -
2 stops8h 20m
Wed 9/92:45 pm -
2 stops7h 35m
Deal found 8/22![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:00 am -
1 stop4h 39m
Fri 10/212:45 pm -
1 stop7h 25m
Deal found 8/20![United Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop5h 43m
Mon 10/57:00 pm -
1 stop5h 37m
Deal found 8/20![United Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 8/24. 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 12/82:36 pm -
1 stop5h 56m
Wed 12/94:50 pm -
1 stop6h 55m
Deal found 8/24![United Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:00 am -
1 stop5h 01m
Tue 10/136:00 am -
3 stops12h 40m
Deal found 8/20![United Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:18 am -
1 stop5h 18m
Tue 9/85:01 pm -
1 stop6h 35m
Deal found 8/20![United Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:52 pm -
1 stop4h 38m
Sat 9/196:00 am -
2 stops9h 33m
Deal found 8/22![United Airlines logo]()
$394
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated August 25, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:36 am -
Nonstop2h 13m
Tue 9/87:10 am -
Nonstop2h 34m
Deal found 8/23![JetBlue logo]()
$275
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:55 am -
Nonstop2h 14m
Tue 9/158:30 am -
Nonstop2h 32m
Deal found 8/21![JetBlue logo]()
$280
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:55 am -
Nonstop2h 14m
Sun 9/138:30 am -
Nonstop2h 32m
Deal found 8/21![JetBlue logo]()
$284
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am -
Nonstop2h 14m
Sat 9/198:30 am -
Nonstop2h 32m
Deal found 8/24![JetBlue logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am -
Nonstop2h 14m
Thu 9/178:30 am -
Nonstop2h 32m
Deal found 8/24![JetBlue logo]()
$273
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:10 pm -
2 stops6h 10m
Sat 9/197:05 am -
1 stop5h 00m
Deal found 8/21![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:50 am -
1 stop5h 30m
Wed 9/2312:50 pm -
2 stops8h 45m
Deal found 8/20![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 8/21. 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.
Wed 9/1611:35 am -
Nonstop2h 33m
Sat 9/1912:15 pm -
Nonstop2h 35m
Deal found 8/21![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am -
1 stop6h 06m
Sat 9/197:05 am -
1 stop5h 25m
Deal found 8/24![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 8/24. 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 9/166:00 am -
1 stop4h 49m
Sat 9/196:35 am -
1 stop6h 02m
Deal found 8/24![Delta logo]()
$309
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:55 am -
Nonstop2h 14m
Sat 9/268:30 am -
Nonstop2h 32m
Deal found 8/21![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 8/21. 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.
Wed 9/236:35 pm -
Nonstop2h 31m
Tue 9/295:40 am -
1 stop4h 08m
Deal found 8/21![Delta logo]()
$267
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 August 25, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Super.com deal was found by Cheapflights users on 8/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:55 am -
Nonstop2h 14m
Deal found 8/22![JetBlue logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:55 am -
Nonstop2h 14m
Deal found 8/23![JetBlue logo]()
$127
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:55 am -
Nonstop2h 14m
Deal found 8/21![JetBlue logo]()
$129
This Super.com deal was found by Cheapflights users on 8/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:10 pm -
1 stop19h 59m
Deal found 8/24![Frontier logo]()
$134
This Super.com deal was found by Cheapflights users on 8/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:36 am -
Nonstop2h 13m
Deal found 8/21![JetBlue logo]()
$136
This Delta deal was found by Cheapflights users on 8/24. 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.
Sat 9/192:35 pm -
Nonstop2h 32m
Deal found 8/24![Delta logo]()
$139
This CheapOair deal was found by Cheapflights users on 8/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
1 stop23h 41m
Deal found 8/21![Frontier logo]()
$140
This Jetabroad deal was found by Cheapflights users on 8/23. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1310:10 am -
1 stop27h 08m
Deal found 8/23![Frontier logo]()
$142
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:00 am -
2 stops6h 47m
Deal found 8/20![United Airlines logo]()
$144
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:40 am -
1 stop6h 48m
Deal found 8/20![United Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 8/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:55 am -
Nonstop2h 14m
Deal found 8/21![JetBlue logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:55 am -
Nonstop2h 14m
Deal found 8/23![JetBlue logo]()
$152
Find flight deals from Milwaukee to Massachusetts
Keep the following information in mind while searching for Milwaukee to Massachusetts flight deals. Data was last updated August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $248 (Cheapflightsfares) |
One-way from | $126 (Super.com) |
Popular in | November |
Cheapest in | May |
Average price | $277 |
Good round-trip deal | $191 or less |
Good one-way deal | $134 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 7,457,451 searches. Data last updated August 25, 2026.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 10/17
12:05 pm-5:37 pm
1 stop4h 32m
Boston Logan Intl
Tue 10/20
5:45 am-11:30 am
2 stops6h 45m
$282
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 9/11
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Tue 9/15
7:00 am-12:43 pm
1 stop6h 43m
$292
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 10/14
10:36 am-4:30 pm
1 stop4h 54m
Boston Logan Intl
Sun 10/18
9:07 am-10:53 am
Nonstop2h 46m
$297
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Tue 9/15
6:00 am-2:36 pm
1 stop7h 36m
Albany Intl
Wed 9/23
3:06 pm-9:54 pm
1 stop7h 48m
$309
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Wed 9/16
6:00 am-11:49 am
1 stop4h 49m
Albany Intl
Sat 9/19
6:35 am-11:37 am
1 stop6h 02m
$309
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Thu 10/15
5:00 am-10:39 am
1 stop4h 39m
Albany Intl
Sat 10/17
6:03 am-1:43 pm
2 stops8h 40m
$314
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Sun 9/6
3:15 pm-9:42 pm
1 stop5h 27m
Hartford Bradley Intl
Thu 9/10
4:50 pm-10:36 pm
1 stop6h 46m
$325
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 9/21
6:25 am-2:30 pm
1 stop7h 05m
Boston Logan Intl
Mon 9/28
5:00 am-9:35 am
1 stop5h 35m
$342
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Tue 9/15
2:20 pm-11:59 pm
2 stops8h 39m
Hartford Bradley Intl
Mon 9/21
6:00 am-10:00 am
1 stop5h 00m
$343
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Wed 10/28
4:00 pm-9:10 pm
1 stop4h 10m
Hartford Bradley Intl
Fri 10/30
7:05 pm-12:35 am
1 stop6h 30m
$345
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-ALB
MKE-BDL
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-ALB
MKE-BDL
MKE-MVY
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $233). Flying from Milwaukee to Massachusetts in November is currently the most expensive (average of $424). 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 August 25, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the afternoon. If you’re flexible enough to do this you can expect to save up to 41% on your trip compared to booking a flight at noon.
Weekly flight availability from Milwaukee to Massachusetts
Explore weekly flight availability from Milwaukee to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 25, 2026.
The most flights from MKE to USMA are scheduled on a Friday (9 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Milwaukee to Massachusetts?
Airfare is typical for this route at the moment.
Milwaukee to Massachusetts flights typically cost between $220 and $340 in September.The cheapest round-trip price found within the last 5 days was $248 on JetBlue (Sep 15-Sep 19).
How far ahead should I book a flight from Milwaukee to Massachusetts?
To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Milwaukee to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Massachusetts. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday 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 August 25, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
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 August 25, 2026.
Popular flight searches
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Milwaukee to Massachusetts flights
Consider these flights traveling from Milwaukee to Massachusetts.
Top 5 airlines flying from Milwaukee to Massachusetts
Discover the top 5 airlines that operate flights from Milwaukee to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$301 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$310 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$336 | FlexibilityNo cancel fee | On-time63% |