$120+ Cheap flights from Massachusetts to Milwaukee (MKE)
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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Milwaukee 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 Massachusetts to Milwaukee
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Cheapest flights from Massachusetts to MilwaukeeExplore the most affordable flight options available from Massachusetts to Milwaukee. 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 Massachusetts to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 1, 2026.
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.
Sat 9/268:30 am -
Nonstop2h 32m
Sun 9/2710:10 am -
1 stop23h 41m
Deal found 8/30![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.
Tue 9/228:30 am -
Nonstop2h 32m
Wed 9/2310:55 am -
Nonstop2h 14m
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 11/193:15 pm -
1 stop20h 28m
Sat 11/2111:38 am -
1 stop6h 33m
Deal found 8/27![Frontier 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.
Sat 10/38:30 am -
Nonstop2h 32m
Sun 10/410:10 am -
1 stop23h 41m
Deal found 8/27![Multiple Airlines logo]()
$273
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:30 am -
Nonstop2h 32m
Sat 10/310:55 am -
Nonstop2h 14m
Deal found 8/28![JetBlue logo]()
$277
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 9/248:30 am -
Nonstop2h 32m
Sun 9/2710:10 am -
1 stop23h 41m
Deal found 8/31![Multiple Airlines logo]()
$281
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.
Wed 9/309:15 am -
Nonstop2h 40m
Sat 10/34:57 pm -
1 stop6h 01m
Deal found 8/27![Delta logo]()
$287
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 9/227:00 pm -
1 stop5h 37m
Wed 9/235:00 am -
1 stop5h 01m
Deal found 8/28![United Airlines logo]()
$292
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:30 am -
Nonstop2h 32m
Tue 9/2210:55 am -
Nonstop2h 14m
Deal found 8/29![JetBlue logo]()
$293
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.
Tue 9/158:30 am -
Nonstop2h 32m
Thu 9/1710:10 am -
1 stop23h 41m
Deal found 8/31![Multiple Airlines logo]()
$294
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 9/306:43 pm -
1 stop5h 16m
Sat 10/36:15 am -
1 stop5h 34m
Deal found 8/31![United Airlines logo]()
$297
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.
Fri 9/118:30 am -
Nonstop2h 32m
Sun 9/1310:10 am -
1 stop23h 41m
Deal found 8/27![Multiple Airlines logo]()
$298
Best flights from Massachusetts to MilwaukeeDiscover carefully curated flight deals from Massachusetts to Milwaukee 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 Massachusetts to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
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.
Tue 9/226:00 am -
1 stop5h 04m
Wed 9/236:35 pm -
Nonstop2h 31m
Deal found 8/28![Delta logo]()
$307
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 9/306:00 am -
2 stops6h 30m
Wed 10/75:00 am -
1 stop4h 49m
Deal found 8/31![United Airlines logo]()
$330
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.
Fri 12/111:20 pm -
2 stops9h 30m
Mon 12/148:00 am -
2 stops7h 10m
Deal found 8/27![Southwest logo]()
$332
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:15 am -
Nonstop2h 40m
Wed 9/236:35 pm -
Nonstop2h 31m
Deal found 8/29![Delta logo]()
$317
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:50 pm -
1 stop4h 55m
Sun 10/46:25 pm -
1 stop4h 45m
Deal found 8/28![Southwest logo]()
$347
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 9/307:00 am -
1 stop5h 23m
Wed 10/72:59 pm -
1 stop8h 00m
Deal found 8/31![Delta logo]()
$325
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 9/96:00 am -
1 stop5h 33m
Sun 9/136:47 pm -
1 stop5h 23m
Deal found 8/31![United Airlines logo]()
$367
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:00 am -
1 stop5h 35m
Mon 10/54:35 pm -
2 stops6h 35m
Deal found 8/29![Southwest logo]()
$352
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.
Thu 10/19:15 am -
Nonstop2h 40m
Mon 10/56:35 pm -
Nonstop2h 31m
Deal found 8/28![Delta logo]()
$327
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.
Tue 11/178:40 am -
1 stop5h 52m
Wed 11/186:47 am -
1 stop7h 14m
Deal found 8/31![United Airlines logo]()
$389
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 10/156:00 am -
1 stop5h 40m
Thu 10/226:50 pm -
1 stop4h 05m
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.
Sat 9/1912:15 pm -
Nonstop2h 35m
Mon 9/216:47 pm -
1 stop4h 11m
Deal found 8/30![Delta logo]()
$337
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.
Mon 9/286:05 am -
1 stop5h 02m
Mon 10/53:52 pm -
2 stops7h 07m
Deal found 8/29![United Airlines 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.
Fri 9/257:04 pm -
1 stop5h 44m
Mon 9/282:55 pm -
1 stop6h 21m
Deal found 8/27![Delta logo]()
$345
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:15 pm -
2 stops7h 05m
Sun 9/203:20 pm -
1 stop7h 30m
Deal found 8/28![Southwest logo]()
$402
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.
Tue 1/266:03 am -
1 stop6h 52m
Thu 1/286:00 am -
1 stop7h 15m
Deal found 8/31![United Airlines logo]()
$405
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 10/71:25 pm -
2 stops9h 55m
Thu 10/810:25 am -
1 stop11h 35m
Deal found 8/31![Southwest logo]()
$402
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.
Tue 11/36:10 am -
1 stop6h 19m
Tue 11/109:35 am -
1 stop5h 44m
Deal found 8/28![Delta logo]()
$367
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.
Fri 9/113:01 pm -
2 stops9h 36m
Tue 9/155:00 am -
1 stop4h 34m
Deal found 8/27![United Airlines logo]()
$416
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:15 pm -
Nonstop2h 37m
Mon 10/56:47 pm -
1 stop4h 11m
Deal found 8/29![Delta logo]()
$372
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/248:20 am -
1 stop4h 40m
Mon 12/287:55 am -
2 stops6h 55m
Deal found 8/28![Southwest logo]()
$417
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 9/135:45 am -
2 stops6h 45m
Thu 9/176:05 am -
1 stop5h 42m
Deal found 8/31![United Airlines logo]()
$432
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 10/86:00 am -
1 stop3h 40m
Sun 10/116:00 am -
1 stop4h 39m
Deal found 8/30![Delta logo]()
$382
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:10 pm -
2 stops7h 55m
Sun 10/255:55 am -
2 stops7h 45m
Deal found 8/28![Southwest logo]()
$424
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.
Tue 10/65:23 am -
1 stop4h 16m
Thu 10/86:49 pm -
1 stop3h 43m
Deal found 8/28![Delta logo]()
$391
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 10/85:35 pm -
1 stop7h 15m
Sun 10/119:45 am -
2 stops14h 30m
Deal found 8/30![Southwest logo]()
$435
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 10/611:55 am -
1 stop5h 36m
Wed 10/77:15 am -
1 stop3h 47m
Deal found 8/31![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.
Sat 9/196:15 am -
1 stop6h 25m
Tue 9/294:57 pm -
1 stop5h 24m
Deal found 8/31![Delta logo]()
$393
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.
Thu 10/87:05 pm -
1 stop5h 48m
Sun 10/116:49 pm -
1 stop3h 43m
Deal found 8/27![Delta logo]()
$417
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 9/119:15 am -
Nonstop2h 40m
Mon 9/146:47 pm -
1 stop4h 11m
Deal found 8/31![Delta logo]()
$442
Last-minute flights from Massachusetts to MilwaukeeDiscover last-minute flight deals from Massachusetts to Milwaukee. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Milwaukee. Data last updated September 1, 2026 and is based on user searches.
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 9/92:05 pm -
1 stop8h 25m
Wed 9/305:30 am -
1 stop6h 30m
Deal found 8/28![Delta logo]()
$325
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.
Fri 9/118:30 am -
Nonstop2h 32m
Sun 9/1310:10 am -
1 stop23h 41m
Deal found 8/27![Multiple Airlines logo]()
$298
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.
Tue 9/158:30 am -
Nonstop2h 32m
Thu 9/1710:10 am -
1 stop23h 41m
Deal found 8/31![Multiple Airlines logo]()
$294
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:30 am -
Nonstop2h 32m
Tue 9/2210:55 am -
Nonstop2h 14m
Deal found 8/29![JetBlue logo]()
$293
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.
Sat 9/198:30 am -
Nonstop2h 32m
Sun 9/2010:10 am -
1 stop23h 41m
Deal found 8/28![Multiple Airlines logo]()
$299
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 9/228:30 am -
Nonstop2h 32m
Wed 9/2310:55 am -
Nonstop2h 14m
Deal found 8/27![JetBlue logo]()
$268
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 9/227:00 pm -
1 stop5h 37m
Wed 9/235:00 am -
1 stop5h 01m
Deal found 8/28![United Airlines logo]()
$292
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 9/248:30 am -
Nonstop2h 32m
Sun 9/2710:10 am -
1 stop23h 41m
Deal found 8/31![Multiple Airlines logo]()
$281
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.
Sat 9/268:30 am -
Nonstop2h 32m
Sun 9/2710:10 am -
1 stop23h 41m
Deal found 8/30![Multiple Airlines logo]()
$260
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:30 am -
Nonstop2h 32m
Sat 10/310:55 am -
Nonstop2h 14m
Deal found 8/28![JetBlue logo]()
$277
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.
Wed 9/309:15 am -
Nonstop2h 40m
Sat 10/34:57 pm -
1 stop6h 01m
Deal found 8/27![Delta logo]()
$287
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 9/306:43 pm -
1 stop5h 16m
Sat 10/36:15 am -
1 stop5h 34m
Deal found 8/31![United Airlines logo]()
$297
One-way flights from Massachusetts to MilwaukeeSearch for one-way flight options from Massachusetts to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Massachusetts to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:13 pm -
1 stop16h 09m
Deal found 8/27![Frontier logo]()
$120
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.
Sat 9/1911:36 am -
1 stop22h 46m
Deal found 8/27![Frontier logo]()
$122
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.
Sat 10/2411:47 am -
1 stop22h 33m
Deal found 8/28![Frontier logo]()
$135
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 9/198:30 am -
Nonstop2h 32m
Deal found 8/27![JetBlue logo]()
$136
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 9/238:30 am -
Nonstop2h 32m
Deal found 8/27![JetBlue logo]()
$137
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:30 am -
Nonstop2h 32m
Deal found 8/28![JetBlue logo]()
$139
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.
Sat 9/2611:36 am -
1 stop22h 46m
Deal found 8/27![Frontier logo]()
$141
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.
Wed 9/236:00 pm -
1 stop5h 21m
Deal found 8/27![Delta logo]()
$149
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.
Sat 9/265:45 am -
2 stops6h 45m
Deal found 8/27![United Airlines logo]()
$154
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 10/56:23 pm -
1 stop6h 25m
Deal found 8/27![Delta logo]()
$155
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 9/267:00 am -
1 stop5h 37m
Deal found 8/28![Delta logo]()
$159
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.
Thu 9/178:30 am -
Nonstop2h 32m
Deal found 8/27![JetBlue logo]()
$161
Find flight deals from Massachusetts to Milwaukee
Keep the following information in mind while searching for Massachusetts to Milwaukee flight deals. Data was last updated September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $260 (CheapOair) |
One-way from | $120 (Jetabroad) |
Popular in | November |
Cheapest in | May |
Average price | $303 |
Good round-trip deal | $148 or less |
Good one-way deal | $259 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Milwaukee 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 Massachusetts to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Tue 9/22
6:00 am-10:04 am
1 stop5h 04m
Milwaukee-Mitchell
Wed 9/23
6:35 pm-10:06 pm
Nonstop2h 31m
$307
Quickest round-trip
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Mon 9/21
9:15 am-10:55 am
Nonstop2h 40m
Milwaukee-Mitchell
Wed 9/23
6:35 pm-10:06 pm
Nonstop2h 31m
$317
HartfordMilwaukee
BDL Hartford Bradley Intl - MKE Milwaukee-Mitchell
BDLMKE
Hartford Bradley Intl
Wed 9/30
7:00 am-11:23 am
1 stop5h 23m
Milwaukee-Mitchell
Wed 10/7
2:59 pm-11:59 pm
1 stop8h 00m
$325
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Thu 10/1
9:15 am-10:55 am
Nonstop2h 40m
Milwaukee-Mitchell
Mon 10/5
6:35 pm-10:06 pm
Nonstop2h 31m
$327
HartfordMilwaukee
BDL Hartford Bradley Intl - MKE Milwaukee-Mitchell
BDLMKE
Hartford Bradley Intl
Wed 9/30
6:00 am-11:30 am
2 stops6h 30m
Milwaukee-Mitchell
Wed 10/7
5:00 am-10:49 am
1 stop4h 49m
$330
AlbanyMilwaukee
ALB Albany Intl - MKE Milwaukee-Mitchell
ALBMKE
Albany Intl
Fri 12/11
1:20 pm-9:50 pm
2 stops9h 30m
Milwaukee-Mitchell
Mon 12/14
8:00 am-4:10 pm
2 stops7h 10m
$332
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Sat 9/19
12:15 pm-1:50 pm
Nonstop2h 35m
Milwaukee-Mitchell
Mon 9/21
6:47 pm-11:58 pm
1 stop4h 11m
$337
HartfordMilwaukee
BDL Hartford Bradley Intl - MKE Milwaukee-Mitchell
BDLMKE
Hartford Bradley Intl
Fri 9/25
7:04 pm-11:48 pm
1 stop5h 44m
Milwaukee-Mitchell
Mon 9/28
2:55 pm-10:16 pm
1 stop6h 21m
$345
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Fri 10/2
7:50 pm-11:45 pm
1 stop4h 55m
Milwaukee-Mitchell
Sun 10/4
6:25 pm-12:10 am
1 stop4h 45m
$347
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Mon 9/28
5:00 am-9:35 am
1 stop5h 35m
Milwaukee-Mitchell
Mon 10/5
4:35 pm-12:10 am
2 stops6h 35m
$352
Showing 1-10 of 55 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Massachusetts with our price prediction graph.
BOS-MKE
BDL-MKE
ALB-MKE
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 Massachusetts to Milwaukee
USMA-MKE
BOS-MKE
BDL-MKE
ALB-MKE
What is the cheapest month to book a flight from Massachusetts to Milwaukee?
Currently, May is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $277). Flying from Massachusetts to Milwaukee in November is currently the most expensive (average of $482). 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 MA to MKE?
Find hourly flight availability from Massachusetts to Milwaukee. 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.
It’s optimal to fly from Massachusetts to Milwaukee at noon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Massachusetts to Milwaukee
Explore weekly flight availability from Massachusetts to Milwaukee. 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 USMA to MKE are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Massachusetts to Milwaukee?
Airfare is typical for this route at the moment.
Massachusetts to Milwaukee flights typically cost between $185 and $387 in September.The cheapest round-trip price found within the last 5 days was $260 on Multiple Airlines (Sep 26-Sep 27).
How far ahead should I book a flight from Massachusetts to Milwaukee?
The best time to book flights from Massachusetts to Milwaukee is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Massachusetts to Milwaukee?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Milwaukee. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Massachusetts to Milwaukee flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Massachusetts to Milwaukee
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Complete your trip
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Search flights from Massachusetts to Milwaukee by cabin class
Find flights from Massachusetts to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
Massachusetts and Milwaukee flights
Browse other Massachusetts and Milwaukee flight options. Last updated on September 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Massachusetts to Milwaukee flights
Consider these flights traveling from Massachusetts to Milwaukee.
Top 5 airlines flying from Massachusetts to Milwaukee
Discover the top 5 airlines that operate flights from Massachusetts to Milwaukee. 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$114 | Average$256 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$367 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$306 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$311 | FlexibilityNo cancel fee | On-time63% |