$122+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 1 — Oct 81
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Massachusetts
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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 1, 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 1, 2026.
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Thu 9/2410:10 am -
1 stop27h 08m
Sat 10/36:13 pm -
1 stop16h 09m
Deal found 9/1![Frontier logo]()
$258
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![Frontier logo]()
$258
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2310:55 am -
Nonstop2h 14m
Sat 9/2611:36 am -
1 stop22h 46m
Deal found 8/27![Multiple Airlines logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![JetBlue logo]()
$268
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop23h 41m
Sat 9/1911:36 am -
1 stop22h 46m
Deal found 8/27![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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
Tue 10/138:23 am -
Nonstop2h 32m
Deal found 8/30![Multiple Airlines logo]()
$273
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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.
Wed 9/2310:55 am -
Nonstop2h 14m
Tue 9/298:30 am -
Nonstop2h 32m
Deal found 8/30![JetBlue logo]()
$277
This CheapOair deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/1010:10 am -
1 stop23h 41m
Sat 9/1211:36 am -
1 stop22h 46m
Deal found 8/30![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop23h 41m
Sat 9/198:30 am -
Nonstop2h 32m
Deal found 8/27![Multiple Airlines logo]()
$279
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/3010:55 am -
Nonstop2h 14m
Wed 10/78:30 am -
Nonstop2h 32m
Deal found 8/27![JetBlue logo]()
$283
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Tue 9/1510:55 am -
Nonstop2h 14m
Sat 9/1911:36 am -
1 stop22h 46m
Deal found 8/27![Multiple Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 8/31![Delta logo]()
$287
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 1, 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 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/266:00 am -
1 stop4h 24m
Sat 10/33:13 pm -
1 stop4h 56m
Deal found 8/29![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/237:50 am -
1 stop7h 10m
Sat 9/265:30 am -
2 stops6h 35m
Deal found 8/31![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/315:30 am -
1 stop5h 09m
Mon 11/25:23 am -
1 stop4h 17m
Deal found 8/31![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/226:50 pm -
1 stop4h 05m
Mon 10/262:50 pm -
2 stops10h 30m
Deal found 8/31![Southwest logo]()
$314
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 am -
1 stop4h 34m
Sat 9/196:10 am -
2 stops9h 23m
Deal found 8/27![United Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/71:45 pm -
2 stops7h 15m
Wed 11/112:35 pm -
2 stops8h 35m
Deal found 8/27![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/317:15 am -
1 stop3h 47m
Sun 11/17:00 am -
1 stop5h 29m
Deal found 8/31![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/24:35 pm -
2 stops6h 30m
Tue 10/135:35 am -
1 stop7h 20m
Deal found 8/30![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/295:00 am -
2 stops8h 14m
Tue 10/69:55 am -
1 stop4h 48m
Deal found 8/28![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 8/31![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/214:00 pm -
1 stop4h 30m
Mon 10/2610:40 am -
2 stops15h 00m
Deal found 8/30![Southwest logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:00 am -
1 stop4h 54m
Thu 10/15:00 pm -
1 stop6h 59m
Deal found 8/27![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/178:00 am -
1 stop5h 49m
Wed 10/214:10 pm -
Nonstop2h 40m
Deal found 8/28![Delta logo]()
$383
This KAYAK deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/1110:55 am -
1 stop25h 17m
Sun 9/131:15 pm -
1 stop21h 47m
Deal found 8/28![Multiple Airlines logo]()
$929
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 8/29![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/287:10 am -
1 stop4h 05m
Fri 10/304:25 pm -
2 stops7h 10m
Deal found 8/31![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/282:59 pm -
1 stop8h 00m
Fri 10/305:23 am -
1 stop4h 13m
Deal found 8/28![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/305:45 pm -
1 stop5h 04m
Sun 11/17:00 am -
1 stop5h 29m
Deal found 8/31![Delta logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/46:15 am -
1 stop5h 33m
Wed 10/146:00 am -
3 stops14h 10m
Deal found 8/28![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/16:50 pm -
1 stop4h 15m
Wed 10/75:35 am -
2 stops9h 15m
Deal found 8/31![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/296:49 pm -
1 stop3h 43m
Fri 10/307:20 am -
1 stop8h 10m
Deal found 8/30![Delta logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 1/2010:27 am -
2 stops6h 56m
Thu 1/286:00 am -
1 stop4h 52m
Deal found 8/31![United Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/36:50 am -
2 stops6h 30m
Tue 10/64:10 pm -
2 stops6h 25m
Deal found 8/30![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/67:09 am -
1 stop3h 36m
Sun 9/65:06 pm -
1 stop4h 12m
Deal found 8/28![Delta logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/115:00 am -
2 stops8h 50m
Sun 9/135:45 am -
2 stops6h 45m
Deal found 8/28![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/246:30 am -
2 stops7h 30m
Tue 10/275:35 am -
1 stop7h 20m
Deal found 8/30![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:30 am -
1 stop6h 30m
Mon 9/215:30 am -
1 stop4h 18m
Deal found 8/27![Delta logo]()
$411
This Southwest deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/292:25 pm -
2 stops8h 30m
Fri 10/304:25 pm -
2 stops8h 55m
Deal found 8/30![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/126:00 am -
2 stops7h 14m
Wed 9/166:00 am -
2 stops6h 30m
Deal found 8/28![United Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/277:18 am -
1 stop6h 46m
Thu 10/16:03 am -
2 stops8h 40m
Deal found 8/31![United Airlines logo]()
$448
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 1, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/1010:10 am -
1 stop23h 41m
Sat 9/1211:36 am -
1 stop22h 46m
Deal found 8/30![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Tue 9/1510:55 am -
Nonstop2h 14m
Sat 9/1911:36 am -
1 stop22h 46m
Deal found 8/27![Multiple Airlines logo]()
$285
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![JetBlue logo]()
$293
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop23h 41m
Sat 9/1911:36 am -
1 stop22h 46m
Deal found 8/27![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop23h 41m
Sat 9/198:30 am -
Nonstop2h 32m
Deal found 8/27![Multiple Airlines logo]()
$279
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2310:55 am -
Nonstop2h 14m
Sat 9/2611:36 am -
1 stop22h 46m
Deal found 8/27![Multiple Airlines logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/27![JetBlue logo]()
$268
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/265:40 am -
1 stop4h 08m
Deal found 8/31![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/237:50 am -
1 stop5h 50m
Sat 9/267:05 am -
1 stop5h 00m
Deal found 8/31![Southwest logo]()
$297
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Thu 9/2410:10 am -
1 stop27h 08m
Sat 10/36:13 pm -
1 stop16h 09m
Deal found 9/1![Frontier logo]()
$258
This Super.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/2610:55 am -
Nonstop2h 14m
Tue 9/298:30 am -
Nonstop2h 32m
Deal found 8/30![JetBlue logo]()
$294
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/3010:55 am -
Nonstop2h 14m
Wed 10/78:30 am -
Nonstop2h 32m
Deal found 8/27![JetBlue logo]()
$283
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 1, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/2710:10 am -
1 stop23h 41m
Deal found 8/28![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/1710:10 am -
1 stop23h 41m
Deal found 8/31![Frontier logo]()
$128
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 8/31![Frontier logo]()
$133
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/810:15 am -
1 stop27h 06m
Deal found 8/31![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1910:55 am -
Nonstop2h 14m
Deal found 8/27![JetBlue logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/2910:55 am -
Nonstop2h 14m
Deal found 8/30![JetBlue logo]()
$137
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2911:35 am -
Nonstop2h 33m
Deal found 8/31![Delta logo]()
$139
This Jetabroad deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Thu 9/1710:10 am -
1 stop27h 08m
Deal found 8/31![Frontier logo]()
$141
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/1010:10 am -
1 stop23h 41m
Deal found 8/27![Frontier logo]()
$141
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 8/31![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/263:51 pm -
1 stop5h 08m
Deal found 8/31![United Airlines logo]()
$149
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/3110:48 am -
2 stops6h 51m
Deal found 8/31![United Airlines logo]()
$154
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 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Frontier) |
One-way from | $122 (CheapOair) |
Popular in | November |
Cheapest in | May |
Average price | $277 |
Good round-trip deal | $227 or less |
Good one-way deal | $151 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 1, 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 9/26
6:00 am-11:24 am
1 stop4h 24m
Boston Logan Intl
Sat 10/3
3:13 pm-7:09 pm
1 stop4h 56m
$297
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 9/23
7:50 am-4:00 pm
1 stop7h 10m
Boston Logan Intl
Sat 9/26
5:30 am-11:05 am
2 stops6h 35m
$302
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Thu 10/22
6:50 pm-11:55 pm
1 stop4h 05m
Albany Intl
Mon 10/26
2:50 pm-12:20 am
2 stops10h 30m
$314
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 11/7
1:45 pm-10:00 pm
2 stops7h 15m
Boston Logan Intl
Wed 11/11
2:35 pm-10:10 pm
2 stops8h 35m
$322
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Sat 10/31
5:30 am-11:39 am
1 stop5h 09m
Hartford Bradley Intl
Mon 11/2
5:23 am-8:40 am
1 stop4h 17m
$325
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 10/2
4:35 pm-12:05 am
2 stops6h 30m
Boston Logan Intl
Tue 10/13
5:35 am-11:55 am
1 stop7h 20m
$327
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 10/21
4:00 pm-9:30 pm
1 stop4h 30m
Boston Logan Intl
Mon 10/26
10:40 am-12:40 am
2 stops15h 00m
$333
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Thu 9/17
5:00 am-10:34 am
1 stop4h 34m
Hartford Bradley Intl
Sat 9/19
6:10 am-2:33 pm
2 stops9h 23m
$348
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Wed 10/28
7:10 am-12:15 pm
1 stop4h 05m
Hartford Bradley Intl
Fri 10/30
4:25 pm-10:35 pm
2 stops7h 10m
$350
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Thu 10/1
6:50 pm-12:05 am
1 stop4h 15m
Boston Logan Intl
Wed 10/7
5:35 am-1:50 pm
2 stops9h 15m
$367
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Milwaukee with our price prediction graph.
MKE-BDL
MKE-BOS
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-BDL
MKE-BOS
MKE-ALB
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 September 1, 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.
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 1, 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 $210 and $354 in October.The cheapest round-trip price found within the last 5 days was $258 on Frontier (Oct 22-Oct 24).
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 29, 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 September 1, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on September 1, 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$246 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$361 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$304 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$313 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$334 | FlexibilityNo cancel fee | On-time63% |