$114+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 October 20, 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 October 20, 2026.
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/58:41 am -
1 stop7h 22m
Mon 12/73:50 pm -
1 stop5h 33m
Deal found 10/16![American Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:35 am -
1 stop6h 55m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/19![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:00 am -
1 stop7h 50m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/18![Southwest logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:40 am -
1 stop6h 59m
Mon 12/710:24 am -
1 stop4h 57m
Deal found 10/15![American Airlines logo]()
$297
This Frontier deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/1910:15 am -
1 stop22h 56m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 10/17![Frontier logo]()
$301
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:50 pm -
1 stop4h 35m
Wed 11/185:10 am -
1 stop5h 30m
Deal found 10/19![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:25 pm -
1 stop4h 30m
Mon 11/165:20 am -
1 stop5h 20m
Deal found 10/19![Southwest logo]()
$315
This Cheapflightsfares deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 11/2311:06 am -
1 stop7h 20m
Deal found 10/15![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:00 am -
1 stop7h 50m
Mon 12/75:30 am -
2 stops6h 30m
Deal found 10/19![Southwest logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop10h 07m
Sat 11/75:36 pm -
1 stop19h 28m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/35:30 am -
2 stops8h 57m
Thu 11/124:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/37:15 am -
2 stops7h 12m
Tue 11/104:00 pm -
2 stops8h 54m
Deal found 10/16![Delta logo]()
$365
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 October 20, 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 October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:25 pm -
1 stop6h 25m
Thu 12/103:30 pm -
2 stops7h 45m
Deal found 10/19![Southwest logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop10h 07m
Sat 11/75:36 pm -
1 stop19h 28m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/35:30 am -
2 stops8h 57m
Fri 11/134:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/45:30 am -
2 stops8h 57m
Tue 11/104:00 pm -
2 stops8h 54m
Deal found 10/16![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/56:25 pm -
1 stop4h 30m
Sat 11/77:25 am -
2 stops9h 25m
Deal found 10/17![Southwest logo]()
$391
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/47:15 am -
2 stops7h 12m
Wed 11/114:00 pm -
2 stops8h 54m
Deal found 10/16![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/66:25 pm -
1 stop4h 30m
Sat 11/75:25 am -
2 stops9h 55m
Deal found 10/17![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:25 pm -
1 stop4h 30m
Mon 11/305:00 pm -
2 stops8h 25m
Deal found 10/19![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/65:30 am -
2 stops8h 57m
Thu 11/124:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$401
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
1 stop10h 21m
Sat 11/286:36 pm -
2 stops26h 24m
Deal found 10/19![American Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 1/87:00 am -
Nonstop2h 23m
Sun 1/107:40 pm -
Nonstop2h 53m
Deal found 10/17![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:35 am -
Nonstop2h 26m
Mon 11/236:30 pm -
Nonstop2h 57m
Deal found 10/19![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:30 pm -
Nonstop2h 23m
Sun 11/226:30 pm -
Nonstop2h 57m
Deal found 10/20![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/257:35 pm -
Nonstop2h 23m
Tue 3/309:00 am -
Nonstop2h 53m
Deal found 10/15![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 3/267:35 pm -
Nonstop2h 23m
Tue 3/303:10 pm -
1 stop6h 58m
Deal found 10/16![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/222:30 pm -
Nonstop2h 23m
Mon 11/307:00 pm -
1 stop5h 54m
Deal found 10/19![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/71:20 pm -
1 stop25h 07m
Wed 11/114:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$516
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/35:30 am -
2 stops8h 57m
Sun 11/84:10 pm -
2 stops17h 40m
Deal found 10/16![Delta logo]()
$531
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated October 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop10h 07m
Sat 11/75:36 pm -
1 stop19h 28m
Deal found 10/19![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/35:30 am -
2 stops8h 57m
Thu 11/124:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/35:30 am -
2 stops8h 57m
Wed 11/114:00 pm -
2 stops8h 54m
Deal found 10/16![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:25 pm -
1 stop4h 30m
Tue 11/107:55 am -
1 stop5h 05m
Deal found 10/19![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/65:30 am -
2 stops8h 57m
Thu 11/124:00 pm -
1 stop7h 15m
Deal found 10/16![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/65:30 am -
2 stops8h 57m
Mon 11/94:00 pm -
2 stops8h 54m
Deal found 10/16![Delta logo]()
$406
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:25 pm -
1 stop4h 30m
Mon 11/165:20 am -
1 stop5h 20m
Deal found 10/19![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:50 pm -
1 stop4h 35m
Wed 11/185:10 am -
1 stop5h 30m
Deal found 10/19![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:00 am -
1 stop7h 50m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/18![Southwest logo]()
$289
This Frontier deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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 10/20![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:35 am -
1 stop6h 55m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/19![Southwest logo]()
$284
This Cheapflightsfares deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 11/2311:06 am -
1 stop7h 20m
Deal found 10/15![Frontier logo]()
$316
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 October 20, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$114
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/57:40 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![American Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$134
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/73:35 pm -
1 stop4h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:35 am -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/62:51 pm -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![American Airlines logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$154
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:50 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:00 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$173
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:30 am -
2 stops8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:30 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:00 am -
1 stop10h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$259
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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (American Airlines) |
One-way from | $114 (Cheapflightsfares) |
Popular in | November |
Cheapest in | May |
Average price | $390 |
Good round-trip deal | $399 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 October 20, 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
Thu 11/5
5:30 am-2:30 pm
2 stops8h 00m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$206
MilwaukeeWorcester
MKE Milwaukee-Mitchell - ORH Worcester
MKEORH
Milwaukee-Mitchell
Tue 11/10
5:20 am-3:19 pm
2 stops8h 59m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
MilwaukeeWorcester
MKE Milwaukee-Mitchell - ORH Worcester
MKEORH
Milwaukee-Mitchell
Tue 11/3
5:30 am-3:27 pm
2 stops8h 57m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 11/13
5:50 pm-11:25 pm
1 stop4h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$213
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 12/6
7:35 am-11:02 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 12/5
12:45 pm-10:00 pm
2 stops8h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$225
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 11/16
6:20 am-2:30 pm
2 stops7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$225
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 1/3
7:09 am-11:58 am
1 stop3h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$229
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 11/3
5:45 am-4:50 pm
1 stop10h 05m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
MilwaukeeWorcester
MKE Milwaukee-Mitchell - ORH Worcester
MKEORH
Milwaukee-Mitchell
Sat 10/31
8:30 am-4:49 pm
1 stop7h 19m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$254
Showing 1-10 of 47 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-ACK
MKE-PVC
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Massachusetts
MKE-USMA
MKE-BOS
MKE-ORH
MKE-ACK
MKE-PVC
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 $235). Flying from Milwaukee to Massachusetts in November is currently the most expensive (average of $434). 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 October 20, 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 37% 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 October 20, 2026.
The most flights from MKE to USMA are scheduled on a Sunday (11 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 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 $320 and $500 in January.The cheapest round-trip price found within the last 5 days was $277 on American Airlines (Jan 20-Jan 28).
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 October 17, 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 October 20, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Massachusetts
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 October 20, 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 October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$382 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$337 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$377 | FlexibilityNo cancel fee | On-time63% |