$74+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Mar 6 — Mar 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Milwaukee to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Massachusetts
Cheapest
Best
Last-minute
One-way
Cheapest flights from Milwaukee to MassachusettsExplore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 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 February 4, 2026.
This United Airlines deal was found by Cheapflights users on 1/31. 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 2/2511:30 am
MKE
- BOS
1 stop4h 49m
United Airlines
Wed 3/116:00 am
BOS
- MKE
1 stop5h 30m
United Airlines
Deal found 1/31![United Airlines logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Fri 5/154:34 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Tue 5/192:09 pm
BOS
- MKE
Nonstop2h 30m
JetBlue
Deal found 2/3![JetBlue logo]()
$196
This JetBlue deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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.
Sat 5/305:09 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Wed 6/32:09 pm
BOS
- MKE
Nonstop2h 30m
JetBlue
Deal found 2/4![JetBlue logo]()
$202
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 5/297:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Wed 6/35:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Deal found 2/4![Delta logo]()
$207
This CheapOair deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 4/1612:03 pm
MKE
- BOS
1 stop21h 18m
Frontier
Mon 4/206:00 am
BOS
- MKE
1 stop11h 13m
Frontier
Deal found 2/4![Frontier logo]()
$213
This American Airlines deal was found by Cheapflights users on 2/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:22 am
MKE
- BOS
1 stop5h 40m
American Airlines
Wed 3/257:16 pm
BOS
- MKE
1 stop4h 51m
American Airlines
Deal found 2/1![American Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/256:00 am
MKE
- BOS
1 stop5h 46m
United Airlines
Wed 3/47:45 am
BOS
- MKE
1 stop5h 50m
United Airlines
Deal found 2/3![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:00 am
MKE
- BOS
1 stop4h 49m
United Airlines
Mon 3/166:23 pm
BOS
- MKE
1 stop4h 50m
United Airlines
Deal found 2/1![United Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Fri 5/14:34 pm
MKE
- BOS
Nonstop2h 15m
Multiple Airlines
Mon 5/46:00 am
BOS
- MKE
1 stop11h 13m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:05 am
MKE
- BOS
1 stop6h 29m
American Airlines
Sat 8/227:41 am
BOS
- MKE
1 stop6h 22m
American Airlines
Deal found 2/1![American Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:39 pm
MKE
- BDL
1 stop15h 44m
Multiple Airlines
Tue 3/109:10 am
BDL
- MKE
1 stop9h 40m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 2/3. 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.
Tue 5/52:50 pm
MKE
- BDL
1 stop8h 09m
Delta
Tue 5/128:05 am
BDL
- MKE
1 stop6h 41m
Delta
Deal found 2/3![Delta logo]()
$263
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 February 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 February 4, 2026.
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Tue 4/74:23 pm
BOS
- MKE
1 stop5h 55m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 5/57:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Fri 5/89:10 am
BOS
- MKE
Nonstop2h 43m
Delta
Deal found 2/4![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 1/31. 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 4/89:15 am
MKE
- BOS
1 stop5h 40m
Southwest
Mon 4/135:30 am
BOS
- MKE
2 stops7h 30m
Southwest
Deal found 1/31![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:00 am
MKE
- BOS
1 stop4h 50m
United Airlines
Tue 3/109:20 am
BOS
- MKE
1 stop5h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:00 am
MKE
- BOS
1 stop4h 49m
United Airlines
Sat 6/66:00 am
BOS
- MKE
1 stop6h 38m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/2. 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 5/65:48 pm
MKE
- BDL
1 stop5h 06m
Delta
Wed 5/136:00 am
BDL
- MKE
1 stop6h 25m
Delta
Deal found 2/2![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:00 am
MKE
- BOS
2 stops6h 53m
United Airlines
Wed 3/116:00 am
BOS
- MKE
1 stop5h 30m
United Airlines
Deal found 2/1![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 1/31. 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.
Sat 4/411:55 am
MKE
- BOS
1 stop7h 10m
Southwest
Wed 4/82:25 pm
BOS
- MKE
2 stops8h 30m
Southwest
Deal found 1/31![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 1/31. 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 5/510:11 am
MKE
- BDL
1 stop7h 19m
Delta
Tue 5/127:05 am
BDL
- MKE
1 stop5h 31m
Delta
Deal found 1/31![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 4/155:50 am
MKE
- BOS
2 stops7h 00m
Southwest
Mon 4/205:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Deal found 2/3![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 2/2. 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 5/65:48 pm
MKE
- BDL
1 stop5h 06m
Delta
Mon 5/117:18 pm
BDL
- MKE
1 stop5h 38m
Delta
Deal found 2/2![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
MKE
- BOS
1 stop5h 49m
United Airlines
Thu 3/268:15 am
BOS
- MKE
1 stop5h 20m
United Airlines
Deal found 2/1![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/2. 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 5/65:33 pm
MKE
- BDL
1 stop5h 26m
Delta
Sat 5/91:02 pm
BDL
- MKE
1 stop4h 03m
Delta
Deal found 2/2![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 4/410:45 am
MKE
- BOS
2 stops9h 15m
United Airlines
Wed 4/86:00 am
BOS
- MKE
1 stop6h 32m
United Airlines
Deal found 2/3![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 2/2. 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 5/46:38 pm
MKE
- BDL
1 stop3h 33m
Delta
Wed 5/136:00 am
BDL
- MKE
1 stop6h 25m
Delta
Deal found 2/2![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/3. 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 4/156:50 am
MKE
- BOS
2 stops8h 32m
United Airlines
Sun 4/196:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Deal found 2/3![United Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:50 am
MKE
- ALB
1 stop7h 10m
Southwest
Sun 5/241:20 pm
ALB
- MKE
2 stops10h 35m
Southwest
Deal found 2/2![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 2/2. 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.
Tue 5/56:38 pm
MKE
- BDL
1 stop3h 33m
Delta
Sat 5/911:54 am
BDL
- MKE
1 stop5h 18m
Delta
Deal found 2/2![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:50 am
MKE
- BDL
1 stop5h 25m
United Airlines
Sat 4/45:05 pm
BDL
- MKE
1 stop5h 13m
United Airlines
Deal found 2/2![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 1/31. 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 2/255:23 am
MKE
- BDL
1 stop7h 16m
Delta
Sat 2/286:05 am
BDL
- MKE
1 stop5h 10m
Delta
Deal found 1/31![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 2/185:30 am
MKE
- ALB
2 stops9h 45m
Southwest
Sat 2/215:15 am
ALB
- MKE
2 stops7h 30m
Southwest
Deal found 2/3![Southwest logo]()
$457
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:49 am
MKE
- ALB
1 stop6h 14m
United Airlines
Sun 5/246:42 pm
ALB
- MKE
1 stop4h 48m
United Airlines
Deal found 2/2![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 2/1. 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.
Thu 6/257:55 pm
MKE
- ALB
1 stop12h 20m
Southwest
Mon 6/2911:20 am
ALB
- MKE
2 stops8h 30m
Southwest
Deal found 2/1![Southwest logo]()
$468
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 3/63:59 pm
MKE
- ALB
1 stop7h 10m
Delta
Mon 3/96:00 am
ALB
- MKE
1 stop3h 50m
Delta
Deal found 2/2![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:10 am
MKE
- ALB
2 stops6h 25m
Southwest
Mon 3/912:05 pm
ALB
- MKE
2 stops8h 45m
Southwest
Deal found 2/2![Southwest logo]()
$483
This Delta deal was found by Cheapflights users on 2/2. 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.
Thu 6/254:20 pm
MKE
- ALB
1 stop6h 18m
Delta
Mon 6/296:30 pm
ALB
- MKE
1 stop5h 57m
Delta
Deal found 2/2![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/186:00 am
MKE
- ALB
2 stops7h 06m
United Airlines
Sat 2/214:50 pm
ALB
- MKE
1 stop5h 05m
United Airlines
Deal found 2/3![United Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 5/222:55 pm
MKE
- ALB
1 stop8h 03m
Delta
Mon 5/256:00 am
ALB
- MKE
1 stop3h 49m
Delta
Deal found 2/2![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 2/3. 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.
Wed 2/185:23 am
MKE
- ALB
1 stop5h 32m
Delta
Sat 2/216:00 am
ALB
- MKE
1 stop8h 16m
Delta
Deal found 2/3![Delta logo]()
$447
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/181:25 pm
MKE
- ALB
1 stop6h 31m
United Airlines
Sun 2/226:00 am
ALB
- MKE
1 stop7h 35m
United Airlines
Deal found 2/3![United Airlines logo]()
$517
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated February 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1712:10 pm
MKE
- BOS
1 stop4h 50m
American Airlines
Thu 2/198:00 am
BOS
- MKE
1 stop4h 40m
American Airlines
Deal found 2/2![American Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:00 am
MKE
- BOS
1 stop4h 46m
American Airlines
Mon 2/235:31 pm
BOS
- MKE
1 stop6h 26m
American Airlines
Deal found 2/2![American Airlines logo]()
$272
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:30 am
MKE
- BOS
1 stop4h 49m
United Airlines
Wed 3/117:16 am
BOS
- MKE
1 stop6h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/255:00 am
MKE
- BOS
2 stops6h 53m
United Airlines
Wed 3/46:00 am
BOS
- MKE
1 stop5h 30m
United Airlines
Deal found 2/3![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:47 pm
MKE
- BOS
1 stop6h 12m
American Airlines
Fri 3/65:47 am
BOS
- MKE
1 stop6h 05m
American Airlines
Deal found 2/3![American Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:39 pm
MKE
- BDL
1 stop15h 44m
Multiple Airlines
Tue 3/109:10 am
BDL
- MKE
1 stop9h 40m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$248
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 3/36:00 am
MKE
- BDL
2 stops6h 54m
United Airlines
Tue 3/104:45 pm
BDL
- MKE
1 stop6h 05m
United Airlines
Deal found 2/3![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/511:30 am
MKE
- BOS
1 stop4h 47m
United Airlines
Thu 3/128:15 am
BOS
- MKE
1 stop5h 20m
United Airlines
Deal found 2/4![United Airlines logo]()
$235
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:10 pm
MKE
- BOS
1 stop4h 50m
American Airlines
Thu 3/127:00 am
BOS
- MKE
1 stop5h 40m
American Airlines
Deal found 2/3![American Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:10 pm
MKE
- BOS
1 stop4h 55m
American Airlines
Fri 3/135:30 pm
BOS
- MKE
1 stop7h 15m
American Airlines
Deal found 2/2![American Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:18 pm
MKE
- BOS
1 stop4h 17m
United Airlines
Fri 3/206:23 pm
BOS
- MKE
1 stop4h 50m
United Airlines
Deal found 2/2![United Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/251:15 pm
MKE
- BOS
1 stop8h 46m
American Airlines
Tue 3/317:00 am
BOS
- MKE
1 stop5h 40m
American Airlines
Deal found 2/3![American Airlines logo]()
$261
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 February 4, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Frontier deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:30 pm
MKE
- BOS
1 stop6h 43m
Frontier
Deal found 2/1![Frontier logo]()
$74
This Expedia deal was found by Cheapflights users on 2/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:08 pm
MKE
- BOS
1 stop6h 43m
Frontier
Deal found 2/3![Frontier logo]()
$80
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:03 pm
MKE
- BOS
1 stop21h 18m
Frontier
Deal found 2/2![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Sat 5/25:09 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 2/3![JetBlue logo]()
$98
This JetBlue deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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.
Mon 5/44:34 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 2/4![JetBlue logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:39 pm
MKE
- BOS
1 stop18h 09m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$103
This Super.com deal was found by Cheapflights users on 2/3. 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.
Sat 2/147:47 pm
MKE
- BOS
1 stop12h 19m
Frontier
Deal found 2/3![Frontier logo]()
$105
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/27:00 am
MKE
- BOS
1 stop4h 46m
United Airlines
Deal found 2/4![United Airlines logo]()
$109
This Trip.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:39 pm
MKE
- BDL
1 stop16h 38m
Frontier
Deal found 2/4![Frontier logo]()
$110
This CheapOair deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 4/1612:03 pm
MKE
- BOS
1 stop21h 18m
Frontier
Deal found 2/4![Frontier logo]()
$113
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 5/65:50 am
MKE
- BOS
2 stops9h 05m
Southwest
Deal found 2/3![Southwest logo]()
$114
This Frontier deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:20 pm
MKE
- BOS
1 stop5h 53m
Frontier
Deal found 2/1![Frontier logo]()
$115
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $165 (United Airlines) |
One-way from | $74 (Frontier) |
Popular in | January |
Cheapest in | September |
Average price | $321 |
Good round-trip deal | $299 or less |
Good one-way deal | $238 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 February 4, 2026.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.
Fly from
Milwaukee
Fly to
Massachusetts
Route
Depart
Return
Price
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sun 4/5
5:10 am-11:01 am
1 stop4h 51m
Boston Logan Intl
Tue 4/7
4:23 pm-9:18 pm
1 stop5h 55m
$217
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 3/3
5:00 am-10:50 am
1 stop4h 50m
Boston Logan Intl
Tue 3/10
9:20 am-1:39 pm
1 stop5h 19m
$217
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 3/18
5:00 am-10:49 am
1 stop4h 49m
Boston Logan Intl
Sat 6/6
6:00 am-11:38 am
1 stop6h 38m
$217
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 2/25
5:00 am-12:53 pm
2 stops6h 53m
Boston Logan Intl
Wed 3/11
6:00 am-10:30 am
1 stop5h 30m
$222
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Tue 5/5
7:58 pm-11:21 pm
Nonstop2h 23m
Boston Logan Intl
Fri 5/8
9:10 am-10:53 am
Nonstop2h 43m
$257
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Wed 4/8
9:15 am-3:55 pm
1 stop5h 40m
Boston Logan Intl
Mon 4/13
5:30 am-12:00 pm
2 stops7h 30m
$262
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Wed 5/6
5:48 pm-11:54 pm
1 stop5h 06m
Hartford Bradley Intl
Wed 5/13
6:00 am-11:25 am
1 stop6h 25m
$263
MilwaukeeHartford
MKE - BDL
MKEBDL
Milwaukee-Mitchell
Tue 5/5
10:11 am-6:30 pm
1 stop7h 19m
Hartford Bradley Intl
Tue 5/12
7:05 am-11:36 am
1 stop5h 31m
$263
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Sat 4/4
11:55 am-8:05 pm
1 stop7h 10m
Boston Logan Intl
Wed 4/8
2:25 pm-9:55 pm
2 stops8h 30m
$277
MilwaukeeBoston
MKE - BOS
MKEBOS
Milwaukee-Mitchell
Thu 3/19
6:00 am-12:49 pm
1 stop5h 49m
Boston Logan Intl
Thu 3/26
8:15 am-12:35 pm
1 stop5h 20m
$277
Showing 1-10 of 60 results
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
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
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $91). Flying from Milwaukee to Massachusetts in August is currently the most expensive (average of $117). 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 February 4, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the evening. 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.
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 January 31, 2026.
Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Monday evenings 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.
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 February 4, 2026.
The most flights from MKE to USMA are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 on average).
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 February 4, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Milwaukee to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Massachusetts by cabin class
Find flights from Milwaukee to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Massachusetts flights
Browse other Milwaukee and Massachusetts flight options. Last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Milwaukee to Massachusetts flights
Consider these flights traveling from Milwaukee to Massachusetts.
Top 5 airlines flying from Milwaukee to Massachusetts
Discover the top 5 airlines that operate flights from Milwaukee to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$271 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$345 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$260 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$280 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$304 | FlexibilityNo cancel fee | On-time69% |