$128+ Cheap flights from Milwaukee (MKE) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 15 — Oct 221
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 September 15, 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 September 15, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/135:55 pm -
1 stop4h 06m
Tue 10/205:50 am -
1 stop5h 06m
Deal found 9/14![Delta logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 06m
Mon 10/193:16 pm -
1 stop19h 04m
Deal found 9/10![Frontier logo]()
$267
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:02 pm -
1 stop4h 34m
Sat 10/177:15 pm -
1 stop5h 19m
Deal found 9/15![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:58 pm -
1 stop7h 26m
Wed 10/141:00 pm -
1 stop6h 36m
Deal found 9/14![American Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 pm -
1 stop4h 20m
Wed 10/76:30 pm -
1 stop4h 50m
Deal found 9/14![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/77:20 am -
1 stop6h 50m
Tue 11/178:40 am -
1 stop4h 20m
Deal found 9/13![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/55:47 pm -
1 stop4h 12m
Wed 10/77:06 pm -
1 stop5h 47m
Deal found 9/15![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/147:18 am -
1 stop6h 11m
Tue 10/206:00 am -
2 stops6h 30m
Deal found 9/14![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:50 pm -
1 stop4h 20m
Tue 10/272:50 pm -
2 stops8h 35m
Deal found 9/14![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/67:10 am -
1 stop6h 00m
Wed 10/72:50 pm -
2 stops8h 35m
Deal found 9/13![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/145:35 am -
1 stop10h 35m
Mon 11/165:05 pm -
1 stop5h 25m
Deal found 9/14![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/53:52 pm -
1 stop4h 30m
Tue 10/62:53 pm -
2 stops9h 44m
Deal found 9/15![United Airlines logo]()
$277
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 September 15, 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 September 15, 2026.
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/63:00 pm -
1 stop6h 20m
Wed 10/72:50 pm -
1 stop8h 30m
Deal found 9/13![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/143:52 pm -
2 stops7h 07m
Tue 10/206:00 am -
2 stops6h 30m
Deal found 9/14![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/102:59 pm -
1 stop5h 20m
Mon 10/125:23 am -
1 stop4h 17m
Deal found 9/15![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/174:35 pm -
1 stop4h 35m
Thu 11/196:25 pm -
1 stop4h 50m
Deal found 9/15![Southwest logo]()
$288
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:00 am -
1 stop4h 49m
Sat 10/176:00 am -
2 stops8h 43m
Deal found 9/10![United Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 9/301:23 pm -
1 stop7h 02m
Thu 10/85:39 am -
1 stop4h 01m
Deal found 9/13![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 12/83:48 pm -
1 stop4h 40m
Wed 12/96:00 am -
1 stop5h 03m
Deal found 9/14![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:20 am -
1 stop4h 20m
Sat 10/178:10 am -
2 stops7h 50m
Deal found 9/13![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/56:35 pm -
Nonstop2h 31m
Wed 10/76:00 am -
1 stop7h 38m
Deal found 9/14![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2012:05 pm -
1 stop4h 32m
Wed 10/215:45 am -
2 stops6h 45m
Deal found 9/14![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/256:25 pm -
1 stop4h 45m
Tue 10/274:15 pm -
1 stop7h 30m
Deal found 9/11![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/46:00 am -
1 stop5h 26m
Tue 10/135:39 am -
1 stop4h 01m
Deal found 9/13![Delta logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 stop6h 11m
Wed 10/216:00 am -
2 stops8h 43m
Deal found 9/14![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/22:35 pm -
2 stops8h 05m
Mon 11/91:20 pm -
2 stops9h 55m
Deal found 9/14![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/144:56 pm -
1 stop5h 31m
Mon 10/195:50 am -
1 stop5h 06m
Deal found 9/10![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:50 am -
2 stops10h 10m
Mon 11/92:25 pm -
2 stops9h 40m
Deal found 9/10![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:52 pm -
1 stop5h 07m
Thu 10/86:00 am -
1 stop5h 07m
Deal found 9/10![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:47 pm -
1 stop4h 12m
Mon 10/55:50 am -
1 stop5h 14m
Deal found 9/14![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/305:55 am -
1 stop4h 05m
Sun 11/16:40 pm -
1 stop4h 30m
Deal found 9/14![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/2110:16 am -
1 stop6h 55m
Thu 10/295:55 am -
1 stop7h 43m
Deal found 9/13![Delta logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/216:15 am -
2 stops6h 59m
Thu 10/295:45 am -
2 stops6h 43m
Deal found 9/13![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:30 am -
1 stop4h 40m
Sun 11/85:55 am -
1 stop7h 10m
Deal found 9/10![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/205:55 pm -
1 stop4h 06m
Mon 10/267:06 pm -
1 stop5h 47m
Deal found 9/11![Delta logo]()
$397
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:32 pm -
1 stop5h 22m
Tue 10/136:00 am -
3 stops14h 10m
Deal found 9/10![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:55 am -
2 stops6h 45m
Sun 11/155:10 am -
1 stop5h 30m
Deal found 9/12![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:49 pm -
1 stop3h 38m
Sun 10/186:00 am -
1 stop3h 40m
Deal found 9/12![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/202:30 pm -
1 stop6h 50m
Wed 10/282:50 pm -
2 stops8h 35m
Deal found 9/13![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:32 pm -
1 stop5h 22m
Sat 10/246:00 am -
3 stops14h 09m
Deal found 9/10![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 10/164:56 pm -
1 stop5h 31m
Mon 10/195:50 am -
1 stop5h 06m
Deal found 9/10![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/26:50 pm -
1 stop4h 15m
Mon 10/125:15 am -
1 stop5h 30m
Deal found 9/14![Southwest logo]()
$412
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 pm -
1 stop4h 20m
Wed 10/76:30 pm -
1 stop4h 50m
Deal found 9/14![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/55:47 pm -
1 stop4h 12m
Wed 10/77:06 pm -
1 stop5h 47m
Deal found 9/15![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/53:52 pm -
1 stop4h 30m
Tue 10/62:53 pm -
2 stops9h 44m
Deal found 9/15![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/63:00 pm -
1 stop6h 20m
Wed 10/72:50 pm -
1 stop8h 30m
Deal found 9/13![Southwest logo]()
$276
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:02 pm -
1 stop4h 34m
Sat 10/177:15 pm -
1 stop5h 19m
Deal found 9/15![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:58 pm -
1 stop7h 26m
Wed 10/141:00 pm -
1 stop6h 36m
Deal found 9/14![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/135:55 pm -
1 stop4h 06m
Tue 10/205:50 am -
1 stop5h 06m
Deal found 9/14![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/147:18 am -
1 stop6h 11m
Tue 10/206:00 am -
2 stops6h 30m
Deal found 9/14![United Airlines logo]()
$274
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:46 am -
Nonstop2h 13m
Sat 10/1711:47 am -
1 stop22h 33m
Deal found 9/10![Multiple Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop27h 06m
Mon 10/193:16 pm -
1 stop19h 04m
Deal found 9/10![Frontier logo]()
$267
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:50 pm -
1 stop4h 45m
Thu 10/295:50 am -
1 stop5h 55m
Deal found 9/14![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:50 pm -
1 stop4h 20m
Tue 10/272:50 pm -
2 stops8h 35m
Deal found 9/14![Southwest logo]()
$275
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 September 15, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/65:55 pm -
1 stop4h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$128
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:15 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$128
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/147:10 am -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/66:10 am -
2 stops7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$133
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:10 am -
1 stop23h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$133
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/75:10 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$135
This CheapOair deal was found by Cheapflights users on 9/10. 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am -
1 stop25h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:50 pm -
1 stop4h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$143
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/78:20 am -
2 stops8h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$147
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:46 am -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$147
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/1411:29 am -
Nonstop2h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$149
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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $255 (Delta) |
One-way from | $128 (Delta) |
Popular in | November |
Cheapest in | May |
Average price | $283 |
Good round-trip deal | $280 or less |
Good one-way deal | $153 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 September 15, 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
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Tue 10/6
5:55 pm-11:01 pm
1 stop4h 06m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Tue 10/6
6:10 am-2:10 pm
2 stops7h 00m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Wed 10/7
5:10 pm-11:59 pm
1 stop5h 49m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Tue 10/27
10:15 am-12:54 pm
1 stop25h 39m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Wed 10/14
2:20 pm-11:59 pm
2 stops8h 39m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Thu 10/8
10:15 am-2:21 pm
1 stop27h 06m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$161
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Mon 10/26
6:02 pm-11:33 pm
1 stop4h 31m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$163
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Tue 10/27
6:47 am-6:42 pm
2 stops10h 55m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$168
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 10/7
8:00 am-2:49 pm
1 stop5h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 10/14
2:20 pm-10:45 pm
2 stops7h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Milwaukee with our price prediction graph.
MKE-ALB
MKE-BDL
MKE-BOS
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-ALB
MKE-BDL
MKE-BOS
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $234). Flying from Milwaukee to Massachusetts in November is currently the most expensive (average of $428). 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 September 15, 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 40% 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 September 15, 2026.
The most flights from MKE to USMA are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 $217 and $367 in October.The cheapest round-trip price found within the last 5 days was $269 on Southwest (Oct 5-Oct 7).
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 September 12, 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. 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 September 15, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - 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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Alternative routes for Milwaukee to Massachusetts
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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 September 15, 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 September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$249 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$367 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$315 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$315 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$339 | FlexibilityNo cancel fee | On-time63% |