$99+ Cheap flights from Milwaukee (MKE) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Cheapest flights from Milwaukee to MassachusettsExplore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 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 August 4, 2026.
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Sat 10/108:10 pm
MKE
- BOS
1 stop11h 10m
Frontier
Mon 10/129:15 am
BOS
- MKE
1 stop11h 00m
Frontier
Deal found 8/2![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 7/31. 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 8/2712:10 pm
MKE
- BOS
1 stop19h 59m
Frontier
Mon 8/3110:04 am
BOS
- MKE
1 stop26h 09m
Frontier
Deal found 7/31![Frontier logo]()
$198
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:55 am
MKE
- BOS
Nonstop2h 14m
Multiple Airlines
Sat 10/1011:05 am
BOS
- MKE
1 stop9h 10m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/118:10 pm
MKE
- BOS
1 stop11h 10m
Multiple Airlines
Tue 10/138:45 am
BOS
- MKE
Nonstop2h 50m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$213
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:03 pm
MKE
- BOS
1 stop12h 13m
Frontier
Mon 11/910:11 am
BOS
- MKE
1 stop9h 57m
Frontier
Deal found 7/30![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Sat 9/268:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 8/3![JetBlue logo]()
$220
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am
MKE
- BOS
Nonstop2h 14m
Multiple Airlines
Sat 9/1911:36 am
BOS
- MKE
1 stop22h 46m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$223
This JetBlue deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/29:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 9/57:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 8/2![JetBlue logo]()
$227
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:36 am
MKE
- BOS
Nonstop2h 13m
Multiple Airlines
Mon 8/3110:04 am
BOS
- MKE
1 stop26h 09m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 7/30. 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.
Tue 9/226:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Tue 9/299:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Deal found 7/30![Delta logo]()
$229
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 9/2110:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Wed 9/238:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 8/3![JetBlue logo]()
$230
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
MKE
- BDL
1 stop22h 22m
Frontier
Sat 9/512:27 pm
BDL
- MKE
1 stop23h 46m
Frontier
Deal found 7/31![Frontier logo]()
$249
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 August 4, 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 August 4, 2026.
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/236:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sat 9/265:40 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 7/29![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 9/1112:30 pm
MKE
- BOS
1 stop6h 10m
Southwest
Tue 9/1510:50 am
BOS
- MKE
2 stops10h 10m
Southwest
Deal found 7/31![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:18 am
MKE
- BDL
1 stop6h 11m
United Airlines
Mon 9/76:00 am
BDL
- MKE
1 stop7h 38m
United Airlines
Deal found 7/30![United Airlines logo]()
$325
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Sun 10/48:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 7/31![JetBlue logo]()
$327
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 9/106:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Mon 9/145:40 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 7/31![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:50 am
MKE
- BOS
1 stop4h 43m
Delta
Mon 8/314:20 pm
BOS
- MKE
Nonstop2h 52m
Delta
Deal found 8/1![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 7/29. 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 10/32:50 pm
MKE
- BOS
1 stop4h 40m
Southwest
Tue 10/62:50 pm
BOS
- MKE
2 stops8h 50m
Southwest
Deal found 7/29![Southwest logo]()
$302
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
MKE
- MVY
1 stop9h 55m
American Airlines
Thu 8/205:25 pm
MVY
- MKE
1 stop20h 31m
American Airlines
Deal found 7/31![American Airlines logo]()
$670
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am
MKE
- ALB
1 stop4h 35m
Southwest
Wed 9/3012:50 pm
ALB
- MKE
2 stops8h 10m
Southwest
Deal found 7/30![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Wed 10/149:00 am
BOS
- MKE
Nonstop2h 46m
Delta
Deal found 8/1![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 am
MKE
- ALB
1 stop4h 24m
United Airlines
Wed 9/94:53 pm
ALB
- MKE
1 stop6h 43m
United Airlines
Deal found 7/30![United Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/115:45 am
MKE
- ALB
1 stop4h 25m
Southwest
Mon 9/146:05 pm
ALB
- MKE
1 stop4h 20m
Southwest
Deal found 8/3![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/316:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Mon 9/75:30 am
BOS
- MKE
1 stop4h 25m
Delta
Deal found 8/2![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 11/186:47 am
MKE
- BDL
1 stop6h 28m
United Airlines
Sun 11/226:00 am
BDL
- MKE
1 stop5h 13m
United Airlines
Deal found 8/3![United Airlines logo]()
$391
This KAYAK deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:36 am
MKE
- PVC
1 stop9h 32m
Multiple Airlines
Fri 9/44:20 pm
PVC
- MKE
1 stop17h 24m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$864
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:45 am
MKE
- BDL
1 stop6h 00m
Southwest
Mon 11/22:30 pm
BDL
- MKE
2 stops9h 35m
Southwest
Deal found 7/30![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 8/266:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Sat 9/512:15 pm
BOS
- MKE
Nonstop2h 46m
Delta
Deal found 7/29![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:25 pm
MKE
- BDL
1 stop4h 45m
Southwest
Sat 9/127:55 am
BDL
- MKE
2 stops8h 50m
Southwest
Deal found 8/1![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:54 pm
MKE
- ALB
1 stop4h 23m
Delta
Wed 9/95:00 pm
ALB
- MKE
1 stop4h 05m
Delta
Deal found 7/31![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/18:20 am
MKE
- ALB
2 stops6h 15m
Southwest
Wed 9/96:00 am
ALB
- MKE
2 stops8h 25m
Southwest
Deal found 7/31![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/166:00 am
MKE
- ALB
1 stop4h 49m
Delta
Sat 9/196:35 am
ALB
- MKE
1 stop6h 02m
Delta
Deal found 8/2![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 10/202:20 pm
MKE
- BOS
2 stops7h 20m
Southwest
Mon 10/262:35 pm
BOS
- MKE
2 stops8h 55m
Southwest
Deal found 7/31![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 9/35:45 am
MKE
- BOS
2 stops5h 45m
Southwest
Tue 9/81:05 pm
BOS
- MKE
1 stop7h 55m
Southwest
Deal found 7/29![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 11/165:59 pm
MKE
- BDL
1 stop4h 43m
Delta
Fri 11/205:30 am
BDL
- MKE
1 stop4h 20m
Delta
Deal found 8/3![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:30 pm
MKE
- BDL
1 stop4h 15m
Southwest
Thu 9/1010:15 am
BDL
- MKE
1 stop6h 45m
Southwest
Deal found 8/1![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 7/31. 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 11/52:35 pm
MKE
- ALB
1 stop7h 00m
Southwest
Sun 11/87:25 am
ALB
- MKE
1 stop5h 40m
Southwest
Deal found 7/31![Southwest logo]()
$366
This United deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:15 am
MKE
- PVC
2 stops9h 25m
Multiple Airlines
Sat 9/124:20 pm
PVC
- MKE
2 stops8h 17m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$909
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
MKE
- MVY
1 stop6h 41m
American Airlines
Sun 8/235:25 pm
MVY
- MKE
1 stop7h 34m
American Airlines
Deal found 7/30![American Airlines logo]()
$942
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/112:00 pm
MKE
- ALB
1 stop7h 40m
Southwest
Sun 9/136:10 am
ALB
- MKE
2 stops8h 25m
Southwest
Deal found 8/3![Southwest logo]()
$378
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:36 am
MKE
- MVY
2 stops29h 34m
Multiple Airlines
Sun 8/238:03 pm
MVY
- MKE
1 stop13h 41m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$910
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated August 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:00 am
MKE
- ALB
1 stop4h 25m
American Airlines
Wed 8/263:38 pm
ALB
- MKE
1 stop5h 21m
American Airlines
Deal found 7/30![American Airlines logo]()
$309
This CheapOair deal was found by Cheapflights users on 7/31. 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 8/2712:10 pm
MKE
- BOS
1 stop19h 59m
Frontier
Mon 8/3110:04 am
BOS
- MKE
1 stop26h 09m
Frontier
Deal found 7/31![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
MKE
- BDL
1 stop22h 22m
Frontier
Sat 9/512:27 pm
BDL
- MKE
1 stop23h 46m
Frontier
Deal found 7/31![Frontier logo]()
$249
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:10 pm
MKE
- BOS
1 stop19h 59m
Multiple Airlines
Sat 9/57:10 am
BOS
- MKE
Nonstop2h 34m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$228
This JetBlue deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Sat 9/57:10 am
BOS
- MKE
Nonstop2h 34m
JetBlue
Deal found 7/30![JetBlue logo]()
$227
This CheapOair deal was found by Cheapflights users on 7/31. 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 9/312:10 pm
MKE
- BOS
1 stop19h 59m
Multiple Airlines
Tue 9/87:10 am
BOS
- MKE
Nonstop2h 34m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Sat 9/198:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 8/3![JetBlue logo]()
$235
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 9/2110:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Wed 9/238:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 8/3![JetBlue logo]()
$230
This Delta deal was found by Cheapflights users on 7/30. 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.
Tue 9/226:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Tue 9/299:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Deal found 7/30![Delta logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Sat 9/268:30 am
BOS
- MKE
Nonstop2h 32m
JetBlue
Deal found 8/3![JetBlue logo]()
$220
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 pm
MKE
- BOS
Nonstop2h 31m
Delta
Sat 9/265:40 am
BOS
- MKE
1 stop4h 08m
Delta
Deal found 7/31![Delta logo]()
$237
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:55 am
MKE
- BOS
Nonstop2h 14m
Multiple Airlines
Sat 10/1011:05 am
BOS
- MKE
1 stop9h 10m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$208
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 August 4, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/1010:10 am
MKE
- BOS
1 stop23h 41m
Frontier
Deal found 8/2![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:03 pm
MKE
- BOS
1 stop13h 06m
Frontier
Deal found 7/30![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 7/31. 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 8/2712:10 pm
MKE
- BOS
1 stop19h 59m
Frontier
Deal found 7/31![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:55 am
MKE
- BOS
Nonstop2h 14m
JetBlue
Deal found 7/31![JetBlue logo]()
$112
This Delta deal was found by Cheapflights users on 7/30. 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.
Wed 9/211:31 am
MKE
- BOS
Nonstop2h 28m
Delta
Deal found 7/30![Delta logo]()
$114
This Delta deal was found by Cheapflights users on 7/30. 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.
Wed 8/266:55 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 7/30![Delta logo]()
$115
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 7/29![JetBlue logo]()
$122
This Delta deal was found by Cheapflights users on 7/30. 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 9/122:35 pm
MKE
- BOS
Nonstop2h 32m
Delta
Deal found 7/30![Delta logo]()
$124
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:43 am
MKE
- BOS
1 stop23h 26m
Frontier
Deal found 7/30![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:03 pm
MKE
- BOS
1 stop12h 13m
Frontier
Deal found 7/30![Frontier logo]()
$130
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 9/104:57 pm
MKE
- BOS
1 stop6h 01m
Delta
Deal found 7/31![Delta logo]()
$134
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:02 pm
MKE
- BDL
1 stop4h 31m
American Airlines
Deal found 7/30![American Airlines logo]()
$163
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Frontier) |
One-way from | $99 (Super.com) |
Popular in | February |
Cheapest in | May |
Average price | $296 |
Good round-trip deal | $222 or less |
Good one-way deal | $138 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 2,558,603 searches. Data last updated August 4, 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 - BOS
MKEBOS
Milwaukee-Mitchell
Wed 9/23
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Sat 9/26
5:40 am-8:48 am
1 stop4h 08m
$239
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 9/10
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Mon 9/14
5:40 am-8:48 am
1 stop4h 08m
$257
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/26
10:50 am-4:33 pm
1 stop4h 43m
Boston Logan Intl
Mon 8/31
4:20 pm-6:12 pm
Nonstop2h 52m
$272
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Fri 9/11
12:30 pm-7:40 pm
1 stop6h 10m
Boston Logan Intl
Tue 9/15
10:50 am-8:00 pm
2 stops10h 10m
$282
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 10/3
2:50 pm-8:30 pm
1 stop4h 40m
Boston Logan Intl
Tue 10/6
2:50 pm-10:40 pm
2 stops8h 50m
$302
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sun 10/4
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Wed 10/14
9:00 am-10:46 am
Nonstop2h 46m
$312
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Mon 8/31
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Mon 9/7
5:30 am-8:55 am
1 stop4h 25m
$312
MilwaukeeAlbany
MKE - ALB
MKEALB
Milwaukee-Mitchell
Wed 9/23
6:00 am-11:35 am
1 stop4h 35m
Albany Intl
Wed 9/30
12:50 pm-8:00 pm
2 stops8h 10m
$314
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 8/26
6:55 pm-10:22 pm
Nonstop2h 27m
Boston Logan Intl
Sat 9/5
12:15 pm-2:01 pm
Nonstop2h 46m
$314
MilwaukeeAlbany
MKE - ALB
MKEALB
Milwaukee-Mitchell
Fri 9/11
5:45 am-11:10 am
1 stop4h 25m
Albany Intl
Mon 9/14
6:05 pm-9:25 pm
1 stop4h 20m
$322
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Milwaukee with our price prediction graph.
MKE-BOS
MKE-BDL
MKE-ALB
MKE-PVC
MKE-MVY
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-BDL
MKE-ALB
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 $234). Flying from Milwaukee to Massachusetts in February is currently the most expensive (average of $419). 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 August 4, 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 47% on your trip compared to booking a flight at noon.
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 $235 and $375 in October.The cheapest round-trip price found within the last 5 days was $188 on Frontier (Oct 10-Oct 12).
How far ahead should I book a flight from Milwaukee to Massachusetts?
To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Milwaukee to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Massachusetts. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated August 4, 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.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Massachusetts
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Complete your trip
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Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on August 4, 2026.
Popular flight searches
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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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$242 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$316 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$304 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$301 | FlexibilityNo cancel fee | On-time69% |