$126+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 7 — Oct 141
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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Cheapest flights from Milwaukee to MassachusettsExplore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
Explore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Thu 12/105:33 pm -
1 stop16h 29m
Sun 12/1311:57 am -
1 stop29h 41m
Deal found 9/3![Frontier logo]()
$258
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/16:32 pm -
1 stop5h 22m
Mon 10/56:43 pm -
1 stop5h 16m
Deal found 9/3![United Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/37:18 am -
1 stop5h 49m
Sun 10/47:01 am -
1 stop5h 29m
Deal found 9/3![United Airlines logo]()
$272
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/306:00 am -
1 stop4h 24m
Sat 10/35:45 am -
2 stops6h 45m
Deal found 9/3![United Airlines logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 -
Nonstop2h 14m
Sat 9/268:30 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$278
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 10/610:55 am -
Nonstop2h 13m
Wed 10/148:23 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$283
This Delta deal was found by Cheapflights users on 9/3. 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 9/301:23 pm -
1 stop7h 02m
Wed 10/79:00 am -
Nonstop2h 46m
Deal found 9/3![Delta logo]()
$287
This Cheapflightsfares deal was found by Cheapflights users on 9/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:55 am -
Nonstop2h 14m
Tue 9/298:30 am -
Nonstop2h 32m
Deal found 9/4![JetBlue logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 9/3010:55 am -
Nonstop2h 14m
Wed 10/78:30 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$293
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Sat 11/77:40 am -
1 stop6h 56m
Tue 11/105:58 pm -
1 stop5h 39m
Deal found 9/3![American Airlines logo]()
$297
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/110:10 am -
1 stop23h 41m
Mon 10/58:30 am -
Nonstop2h 32m
Deal found 9/7![Multiple Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 9/3. 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 11/62:30 pm -
Nonstop2h 10m
Mon 11/96:35 pm -
1 stop5h 30m
Deal found 9/3![Southwest logo]()
$299
Best flights from Milwaukee to MassachusettsDiscover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
Discover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/12:25 pm -
1 stop7h 55m
Mon 10/56:00 am -
1 stop5h 40m
Deal found 9/3![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/155:00 am -
1 stop5h 01m
Wed 10/216:43 pm -
1 stop5h 16m
Deal found 9/5![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 9/3. 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 9/301:23 pm -
1 stop7h 02m
Thu 10/85:39 am -
1 stop4h 01m
Deal found 9/3![Delta logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Thu 10/810:15 am -
1 stop27h 06m
Mon 10/121:04 pm -
2 stops21h 16m
Deal found 9/5![Multiple Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/15:11 pm -
1 stop5h 38m
Mon 10/57:04 pm -
1 stop5h 14m
Deal found 9/6![American Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 9/3. 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 11/66:25 pm -
1 stop4h 20m
Mon 11/92:30 pm -
2 stops8h 40m
Deal found 9/3![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Fri 10/22:20 pm -
2 stops7h 25m
Tue 10/136:00 am -
1 stop5h 07m
Deal found 9/3![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 9/3. 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.
Sun 9/276:00 am -
1 stop4h 38m
Thu 10/15:00 pm -
1 stop4h 05m
Deal found 9/3![Delta logo]()
$404
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 1/146:00 am -
2 stops8h 05m
Sun 1/1712:40 pm -
2 stops9h 00m
Deal found 9/3![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:30 am -
1 stop4h 37m
Wed 10/75:45 am -
2 stops6h 45m
Deal found 9/6![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/3011:35 am -
Nonstop2h 33m
Sun 10/45:40 am -
1 stop4h 13m
Deal found 9/7![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/115:55 am -
1 stop4h 00m
Wed 10/1412:55 pm -
1 stop4h 25m
Deal found 9/7![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 10/46:15 am -
1 stop5h 33m
Wed 10/149:51 am -
2 stops10h 19m
Deal found 9/4![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 9/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:45 am -
2 stops8h 25m
Mon 11/1612:30 pm -
2 stops9h 55m
Deal found 9/4![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:03 am -
1 stop8h 12m
Sun 10/185:23 am -
1 stop4h 17m
Deal found 9/7![Delta logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/25:00 am -
1 stop4h 49m
Sun 10/46:00 am -
2 stops8h 43m
Deal found 9/6![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 9/3. 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.
Tue 10/136:10 am -
2 stops8h 30m
Sat 10/171:10 pm -
2 stops7h 55m
Deal found 9/3![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:13 pm -
Nonstop2h 19m
Sun 11/156:30 pm -
Nonstop2h 57m
Deal found 9/6![Delta logo]()
$469
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 10/47:18 am -
1 stop6h 11m
Sun 10/116:00 am -
2 stops6h 30m
Deal found 9/4![United Airlines logo]()
$443
This Southwest deal was found by Cheapflights users on 9/3. 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 9/236:00 am -
1 stop5h 00m
Fri 10/24:25 pm -
2 stops8h 50m
Deal found 9/3![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/139:17 am -
2 stops7h 10m
Sun 11/156:00 am -
3 stops9h 58m
Deal found 9/7![United Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 9/4. 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 9/185:47 pm -
1 stop4h 12m
Sun 9/206:35 am -
1 stop4h 25m
Deal found 9/4![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Sun 9/277:18 am -
1 stop6h 46m
Thu 10/16:03 am -
2 stops8h 40m
Deal found 9/2![United Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:25 pm -
2 stops8h 40m
Tue 10/135:35 am -
2 stops9h 15m
Deal found 9/6![Southwest logo]()
$457
This KAYAK deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Fri 10/1610:46 am -
1 stop20h 42m
Sun 10/184:20 pm -
1 stop18h 35m
Deal found 9/5![Multiple Airlines logo]()
$833
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/202:20 pm -
2 stops7h 25m
Mon 10/267:31 am -
1 stop7h 01m
Deal found 9/3![United Airlines logo]()
$453
This KAYAK deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Thu 10/1510:46 am -
1 stop20h 42m
Sun 10/184:20 pm -
1 stop18h 35m
Deal found 9/5![Multiple Airlines logo]()
$853
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:45 am -
1 stop4h 25m
Fri 9/253:10 pm -
2 stops6h 10m
Deal found 9/5![Southwest logo]()
$482
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Wed 9/306:19 am -
2 stops9h 40m
Thu 10/86:00 am -
1 stop5h 07m
Deal found 9/4![United Airlines logo]()
$463
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:25 pm -
2 stops8h 30m
Sun 10/184:10 pm -
1 stop7h 20m
Deal found 9/5![Southwest logo]()
$509
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated September 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:55 am -
Nonstop2h 14m
Tue 9/298:30 am -
Nonstop2h 32m
Deal found 9/4![JetBlue logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 -
Nonstop2h 14m
Sat 9/268:30 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/3. 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 9/306:00 am -
1 stop4h 24m
Sat 10/35:45 am -
2 stops6h 45m
Deal found 9/3![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 9/3. 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 9/301:23 pm -
1 stop7h 02m
Wed 10/79:00 am -
Nonstop2h 46m
Deal found 9/3![Delta logo]()
$287
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 9/3010:55 am -
Nonstop2h 14m
Wed 10/78:30 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$293
This American Airlines deal was found by Cheapflights users on 9/3. 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 9/301:18 pm -
1 stop5h 12m
Wed 10/76:16 pm -
1 stop5h 26m
Deal found 9/3![American Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/16:32 pm -
1 stop5h 22m
Mon 10/56:43 pm -
1 stop5h 16m
Deal found 9/3![United Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/110:10 am -
1 stop23h 41m
Mon 10/58:30 am -
Nonstop2h 32m
Deal found 9/7![Multiple Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 9/3. 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.
Thu 10/12:25 pm -
1 stop7h 55m
Mon 10/56:00 am -
1 stop5h 40m
Deal found 9/3![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/37:18 am -
1 stop5h 49m
Sun 10/47:01 am -
1 stop5h 29m
Deal found 9/3![United Airlines logo]()
$272
This Cheapflightsfares deal was found by Cheapflights users on 9/3. 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 10/610:55 am -
Nonstop2h 13m
Wed 10/148:23 am -
Nonstop2h 32m
Deal found 9/3![JetBlue logo]()
$283
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:35 pm -
Nonstop2h 27m
Tue 10/136:00 am -
1 stop7h 38m
Deal found 9/6![Delta logo]()
$307
One-way flights from Milwaukee to MassachusettsSearch for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Super.com deal was found by Cheapflights users on 9/2. 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 10/1510:15 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/110:10 am -
1 stop23h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 9/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:10 am -
1 stop23h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$134
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Sun 10/410:10 am -
1 stop23h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$135
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/76:00 am -
1 stop4h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![United Airlines logo]()
$136
This JetBlue deal was found by Cheapflights users on 9/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:55 am -
Nonstop2h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![JetBlue logo]()
$139
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Thu 10/810:15 am -
1 stop27h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$140
This CheapOair deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/2010:10 am -
1 stop27h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$141
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Thu 9/2410:10 am -
1 stop23h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Thu 12/35:33 pm -
1 stop16h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$145
This Super.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/2210:55 am -
Nonstop2h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![JetBlue logo]()
$146
This KAYAK deal was found by Cheapflights users on 9/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:55 am -
Nonstop2h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![JetBlue logo]()
$148
Find flight deals from Milwaukee to Massachusetts
Keep the following information in mind while searching for Milwaukee to Massachusetts flight deals. Data was last updated September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (CheapOair) |
One-way from | $126 (Super.com) |
Popular in | November |
Cheapest in | May |
Average price | $278 |
Good round-trip deal | $257 or less |
Good one-way deal | $151 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 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
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Sun 9/20
10:10 am-2:18 pm
1 stop27h 08m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 9/29
11:35 am-3:08 pm
Nonstop2h 33m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 9/29
3:10 pm-9:25 pm
1 stop5h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 10/11
5:00 am-11:00 am
1 stop5h 00m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Quickest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 10/5
6:35 pm-10:06 pm
Nonstop2h 31m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 11/4
10:48 am-5:24 pm
1 stop5h 36m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Mon 11/2
6:00 am-1:00 pm
1 stop6h 00m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Mon 11/2
10:20 am-7:30 pm
2 stops8h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
MilwaukeeAlbany
MKE Milwaukee-Mitchell - ALB Albany Intl
MKEALB
Milwaukee-Mitchell
Sun 10/11
5:00 am-11:46 am
1 stop5h 46m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
MilwaukeeHartford
MKE Milwaukee-Mitchell - BDL Hartford Bradley Intl
MKEBDL
Milwaukee-Mitchell
Fri 10/2
2:20 pm-11:59 pm
2 stops8h 39m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
Showing 1-10 of 56 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-ALB
MKE-BDL
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-ALB
MKE-BDL
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 $233). Flying from Milwaukee to Massachusetts in November is currently the most expensive (average of $420). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MKE to MA?
Find hourly flight availability from Milwaukee to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 7, 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 44% 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 typical for this route at the moment.
Milwaukee to Massachusetts flights typically cost between $215 and $356 in December.The cheapest round-trip price found within the last 5 days was $258 on Frontier (Dec 10-Dec 13).
How far ahead should I book a flight from Milwaukee to Massachusetts?
To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Milwaukee to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Massachusetts. Price data was last updated on September 5, 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. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated September 7, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 7, 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 September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$364 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$313 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$314 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$338 | FlexibilityNo cancel fee | On-time63% |