$143+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 29 — Nov 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 29, 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 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 11/1910:15 am -
1 stop22h 56m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 9/24![Frontier logo]()
$279
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Sun 10/1810:15 am -
1 stop23h 47m
Sat 10/2411:47 am -
1 stop22h 33m
Deal found 9/24![Frontier logo]()
$294
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:11 pm -
1 stop15h 00m
Fri 11/2711:06 am -
1 stop7h 20m
Deal found 9/29![Frontier logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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.
Sun 11/226:11 pm -
1 stop15h 00m
Fri 11/2711:06 am -
1 stop7h 20m
Deal found 9/27![Frontier logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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.
Thu 11/1910:15 am -
1 stop22h 56m
Fri 11/2711:06 am -
1 stop7h 20m
Deal found 9/27![Frontier logo]()
$314
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/1510:15 am -
1 stop23h 47m
Mon 10/1911:47 am -
1 stop22h 33m
Deal found 9/24![Frontier logo]()
$328
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:11 pm -
1 stop15h 00m
Mon 11/2311:06 am -
1 stop7h 20m
Deal found 9/26![Frontier logo]()
$329
This CheapOair deal was found by Cheapflights users on 9/27. 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 10/1310:46 am -
Nonstop2h 13m
Sat 10/1711:47 am -
1 stop22h 33m
Deal found 9/27![Multiple Airlines logo]()
$348
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares 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 9/29![Frontier logo]()
$350
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:30 pm -
Nonstop2h 10m
Mon 11/99:00 am -
Nonstop2h 55m
Deal found 9/25![Southwest logo]()
$351
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop5h 20m
Tue 11/105:43 am -
1 stop6h 25m
Deal found 9/27![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:10 am -
1 stop10h 30m
Tue 11/104:41 pm -
1 stop6h 56m
Deal found 9/29![American Airlines logo]()
$358
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 29, 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 29, 2026.
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:30 pm -
Nonstop2h 10m
Mon 11/99:00 am -
Nonstop2h 55m
Deal found 9/26![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/176:00 am -
1 stop4h 24m
Sat 10/246:00 am -
1 stop5h 07m
Deal found 9/24![United Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop11h 38m
Sun 12/67:04 pm -
1 stop18h 04m
Deal found 9/28![American Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:30 pm -
Nonstop2h 23m
Mon 11/1610:50 am -
Nonstop2h 54m
Deal found 9/25![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:35 am -
1 stop10h 35m
Mon 11/93:30 pm -
2 stops9h 05m
Deal found 9/29![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 12/287:00 pm -
1 stop5h 18m
Sat 1/26:38 pm -
1 stop5h 33m
Deal found 9/28![United Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:38 pm -
1 stop5h 00m
Mon 12/77:04 pm -
1 stop18h 04m
Deal found 9/28![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 9/27. 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.
Fri 11/131:13 pm -
Nonstop2h 19m
Mon 11/1610:50 am -
Nonstop2h 54m
Deal found 9/27![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 9/24. 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.
Sat 10/172:50 pm -
1 stop4h 45m
Sat 10/2412:00 pm -
2 stops9h 05m
Deal found 9/24![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 9/24. 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 10/166:35 pm -
Nonstop2h 27m
Sat 10/2412:15 pm -
Nonstop2h 40m
Deal found 9/24![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 9/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:30 am -
2 stops8h 00m
Thu 11/191:20 pm -
2 stops9h 10m
Deal found 9/28![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/27. 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.
Thu 11/196:20 am -
2 stops7h 10m
Fri 11/278:40 am -
1 stop4h 25m
Deal found 9/27![Southwest logo]()
$396
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:42 am -
2 stops28h 07m
Sat 10/175:16 pm -
2 stops27h 42m
Deal found 9/28![American Airlines logo]()
$508
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:15 am -
2 stops6h 43m
Wed 10/144:15 pm -
1 stop6h 09m
Deal found 9/29![Delta logo]()
$482
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:25 pm -
1 stop4h 25m
Tue 11/31:20 pm -
2 stops9h 05m
Deal found 9/26![Southwest logo]()
$403
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:00 am -
1 stop11h 38m
Mon 1/184:12 pm -
1 stop20h 52m
Deal found 9/25![American Airlines logo]()
$517
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:15 am -
2 stops6h 43m
Mon 10/124:15 pm -
1 stop6h 09m
Deal found 9/26![Delta logo]()
$493
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:19 pm -
2 stops20h 30m
Fri 10/165:16 pm -
2 stops26h 15m
Deal found 9/27![American Airlines logo]()
$533
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 29, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Sun 10/410:10 am -
1 stop23h 41m
Wed 10/148:23 am -
Nonstop2h 32m
Deal found 9/27![Multiple Airlines logo]()
$378
This CheapOair deal was found by Cheapflights users on 9/27. 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 10/1310:46 am -
Nonstop2h 13m
Sat 10/1711:47 am -
1 stop22h 33m
Deal found 9/27![Multiple Airlines logo]()
$348
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/1510:15 am -
1 stop23h 47m
Mon 10/1911:47 am -
1 stop22h 33m
Deal found 9/24![Frontier logo]()
$328
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:51 pm -
1 stop5h 08m
Tue 10/276:00 am -
1 stop5h 23m
Deal found 9/25![United Airlines logo]()
$367
This CheapOair deal was found by Cheapflights users on 9/24. 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.
Sat 10/1710:46 am -
Nonstop2h 13m
Sat 10/2411:47 am -
1 stop22h 33m
Deal found 9/24![Multiple Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/24. 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.
Sat 10/174:35 pm -
1 stop4h 35m
Sat 10/245:25 am -
1 stop5h 15m
Deal found 9/24![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/176:15 am -
1 stop5h 33m
Sat 10/246:00 am -
1 stop5h 48m
Deal found 9/27![United Airlines logo]()
$382
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Sun 10/1810:15 am -
1 stop23h 47m
Sat 10/2411:47 am -
1 stop22h 33m
Deal found 9/24![Frontier logo]()
$294
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:02 pm -
1 stop4h 37m
Mon 10/265:45 pm -
1 stop6h 49m
Deal found 9/29![American Airlines logo]()
$372
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares 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 9/29![Frontier logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop9h 17m
Sun 11/85:43 am -
1 stop6h 25m
Deal found 9/29![American Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:05 am -
2 stops8h 50m
Sun 11/85:10 am -
1 stop5h 30m
Deal found 9/29![Southwest logo]()
$379
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 29, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$143
This Super.com deal was found by Cheapflights users on 9/27. 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.
Sun 10/2510:15 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares 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 9/25![Frontier logo]()
$163
This CheapOair deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:15 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$170
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:30 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:46 am -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:52 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![United Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:30 am -
1 stop10h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![American Airlines logo]()
$185
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 pm -
2 stops22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:19 pm -
2 stops20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$243
This Delta deal was found by Cheapflights users on 9/27. 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.
Sun 10/117:15 am -
2 stops6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Delta logo]()
$254
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:10 am -
1 stop9h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$314
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Cheapflightsfares) |
One-way from | $143 (Cheapflightsfares) |
Popular in | November |
Cheapest in | May |
Average price | $284 |
Good round-trip deal | $317 or less |
Good one-way deal | $208 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 29, 2026.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 11/6
2:30 pm-5:40 pm
Nonstop2h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$176
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Thu 10/22
6:32 pm-12:54 am
1 stop5h 22m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 10/21
2:58 pm-10:37 pm
1 stop6h 39m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$190
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 11/7
1:45 pm-10:05 pm
2 stops7h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 10/25
5:00 am-10:18 am
1 stop4h 18m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 10/24
6:30 am-3:20 pm
2 stops7h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 10/31
6:35 am-5:20 pm
2 stops9h 45m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 10/30
6:35 pm-10:02 pm
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 11/24
7:35 am-11:01 am
Nonstop2h 26m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 10/24
2:40 pm-6:10 pm
Nonstop2h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
Showing 1-10 of 39 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-ORH
MKE-HYA
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-ORH
MKE-HYA
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 $430). 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 29, 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 29, 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 below average for this route at the moment.
Milwaukee to Massachusetts flights typically cost between $286 and $457 in November.The cheapest round-trip price found within the last 5 days was $279 on Frontier (Nov 19-Nov 22).
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 26, 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. Monday 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 29, 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
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Milwaukee to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Massachusetts by cabin class
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 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$115 | Average$249 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$331 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$322 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$346 | FlexibilityNo cancel fee | On-time63% |