$136+ Cheap flights from Wisconsin 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Nov 7 — Nov 141
Round-trip
1 adult, Economy
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Cheapest flights from Wisconsin to MassachusettsExplore the most affordable flight options available from Wisconsin to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
Explore the most affordable flight options available from Wisconsin to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/94:05 pm -
1 stop6h 40m
Thu 11/124:20 pm -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 10/282:30 pm -
1 stop7h 15m
Sat 10/3112:15 pm -
1 stop4h 10m
Deal found 10/7![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/95:10 am -
1 stop5h 30m
Deal found 10/8![Southwest logo]()
$279
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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.
Fri 11/206:11 pm -
1 stop15h 00m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 10/4![Frontier logo]()
$284
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sat 10/315:35 am -
1 stop10h 30m
Mon 11/99:00 am -
Nonstop2h 55m
Deal found 10/6![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 10/7. 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 12/2312:36 pm -
1 stop8h 19m
Sat 12/265:30 am -
1 stop7h 26m
Deal found 10/7![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Wed 11/42:26 pm -
1 stop6h 04m
Sat 11/76:36 pm -
1 stop5h 55m
Deal found 10/7![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:30 pm -
1 stop5h 28m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/8![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Sat 12/1912:22 pm -
1 stop6h 07m
Sat 1/92:25 pm -
2 stops7h 52m
Deal found 10/7![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 10/7. 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 11/54:51 pm -
1 stop6h 29m
Mon 11/95:45 am -
1 stop6h 57m
Deal found 10/7![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:35 pm -
1 stop5h 45m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/8![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/77:02 am -
2 stops8h 55m
Mon 11/95:43 am -
1 stop6h 10m
Deal found 10/8![American Airlines logo]()
$340
Best flights from Wisconsin to MassachusettsDiscover carefully curated flight deals from Wisconsin to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
Discover carefully curated flight deals from Wisconsin to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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.
Thu 12/38:00 am -
1 stop7h 50m
Tue 12/82:35 pm -
2 stops8h 35m
Deal found 10/5![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 10/6. 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.
Wed 12/236:33 pm -
1 stop4h 26m
Sat 12/265:30 am -
1 stop7h 26m
Deal found 10/6![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Sat 12/1912:22 pm -
1 stop6h 07m
Sat 1/96:00 am -
1 stop6h 57m
Deal found 10/7![United Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/286:00 am -
1 stop5h 07m
Sun 11/17:13 am -
1 stop7h 46m
Deal found 10/3![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/96:25 pm -
1 stop4h 30m
Thu 11/122:25 pm -
2 stops9h 45m
Deal found 10/7![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 10/6. 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.
Sat 12/196:33 pm -
1 stop4h 26m
Sat 1/94:40 pm -
1 stop5h 02m
Deal found 10/6![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Wed 11/45:05 am -
1 stop6h 41m
Sat 11/74:56 pm -
1 stop7h 35m
Deal found 10/7![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Sat 11/212:37 pm -
1 stop7h 49m
Mon 11/235:20 pm -
2 stops7h 47m
Deal found 10/6![American Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 10/4. 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.
Sat 10/315:45 pm -
1 stop5h 14m
Sat 11/77:27 am -
1 stop5h 11m
Deal found 10/4![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/88:00 am -
2 stops8h 41m
Sat 12/124:45 pm -
1 stop5h 54m
Deal found 10/8![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 10/3. 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 10/304:42 pm -
1 stop4h 55m
Fri 11/65:43 am -
1 stop6h 18m
Deal found 10/3![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:30 pm -
1 stop5h 28m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/5![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Sat 11/215:55 pm -
1 stop5h 51m
Mon 11/233:01 pm -
1 stop5h 09m
Deal found 10/4![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/304:42 pm -
1 stop4h 55m
Thu 11/55:43 am -
1 stop6h 18m
Deal found 10/6![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/4. 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.
Thu 11/54:51 pm -
1 stop6h 29m
Mon 11/95:30 am -
1 stop5h 58m
Deal found 10/4![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/5. 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 10/294:47 pm -
1 stop6h 59m
Tue 11/310:25 am -
1 stop6h 21m
Deal found 10/5![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/234:55 pm -
1 stop5h 04m
Wed 12/305:51 am -
1 stop7h 25m
Deal found 10/5![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/7. 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 2/37:00 am -
1 stop4h 01m
Mon 2/154:40 pm -
1 stop4h 57m
Deal found 10/7![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/4. 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 1/209:55 am -
2 stops7h 35m
Thu 1/282:57 pm -
1 stop5h 20m
Deal found 10/4![United Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:46 am -
2 stops9h 51m
Tue 12/85:56 pm -
1 stop7h 31m
Deal found 10/5![American Airlines logo]()
$354
This United deal was found by Cheapflights users on 10/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:48 am -
2 stops9h 51m
Sat 11/73:24 pm -
2 stops8h 26m
Deal found 10/3![Multiple Airlines logo]()
$1,081
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:38 pm -
1 stop5h 06m
Tue 11/177:15 am -
1 stop5h 27m
Deal found 10/5![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/3. 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.
Fri 11/65:35 pm -
1 stop5h 45m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/3![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/3. 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 12/47:00 am -
2 stops6h 32m
Mon 12/71:35 pm -
1 stop4h 43m
Deal found 10/3![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 10/4. 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.
Sat 12/264:52 pm -
1 stop6h 03m
Fri 1/111:39 am -
1 stop5h 23m
Deal found 10/4![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/3. 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 11/72:40 pm -
2 stops7h 33m
Fri 11/137:40 pm -
1 stop5h 26m
Deal found 10/3![American Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 10/6. 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 11/277:00 pm -
1 stop4h 46m
Tue 12/227:40 pm -
1 stop5h 00m
Deal found 10/6![United Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/4. 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 12/254:52 pm -
1 stop5h 47m
Fri 1/111:39 am -
1 stop5h 23m
Deal found 10/4![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/3. 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 2/65:15 am -
1 stop7h 40m
Tue 2/94:54 pm -
1 stop7h 41m
Deal found 10/3![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:37 pm -
1 stop6h 43m
Sat 11/712:45 pm -
Nonstop2h 49m
Deal found 10/5![Delta logo]()
$373
Last-minute flights from Wisconsin to MassachusettsDiscover last-minute flight deals from Wisconsin to Massachusetts. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Massachusetts. Data last updated October 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 10/282:30 pm -
1 stop7h 15m
Sat 10/3112:15 pm -
1 stop4h 10m
Deal found 10/7![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sat 10/315:35 am -
1 stop10h 30m
Mon 11/99:00 am -
Nonstop2h 55m
Deal found 10/6![Southwest logo]()
$285
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Wed 11/45:05 am -
1 stop6h 41m
Sat 11/74:56 pm -
1 stop7h 35m
Deal found 10/7![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/7. 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 11/54:51 pm -
1 stop6h 29m
Mon 11/95:45 am -
1 stop6h 57m
Deal found 10/7![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/95:10 am -
1 stop5h 30m
Deal found 10/8![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:35 pm -
1 stop5h 45m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/8![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:30 pm -
1 stop5h 28m
Mon 11/95:45 am -
1 stop7h 07m
Deal found 10/8![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/77:02 am -
2 stops8h 55m
Mon 11/95:43 am -
1 stop6h 10m
Deal found 10/8![American Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/94:05 pm -
1 stop6h 40m
Thu 11/124:20 pm -
1 stop6h 55m
Deal found 10/7![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 10/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:35 pm -
1 stop5h 09m
Tue 11/175:45 am -
1 stop7h 07m
Deal found 10/5![Delta logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Sat 11/149:35 am -
2 stops8h 18m
Tue 11/173:01 pm -
1 stop5h 07m
Deal found 10/5![United Airlines logo]()
$336
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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.
Fri 11/206:11 pm -
1 stop15h 00m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 10/4![Frontier logo]()
$284
One-way flights from Wisconsin to MassachusettsSearch for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
Search for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/7. 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.
Tue 11/1012:45 pm -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$136
This Southwest deal was found by Cheapflights users on 10/5. 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 10/266:50 pm -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$141
This Cheapflightsfares deal was found by Cheapflights users on 10/4. 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.
Wed 11/256:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$143
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/62:30 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 10/6. 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.
Tue 10/272:20 pm -
2 stops7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 10/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:38 am -
2 stops22h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:24 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:10 pm -
1 stop15h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:30 am -
3 stops46h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$219
Find flight deals from Wisconsin to Massachusetts
Keep the following information in mind while searching for Wisconsin to Massachusetts flight deals. Data was last updated October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $272 (Southwest) |
One-way from | $136 (Southwest) |
Popular in | November |
Cheapest in | May |
Average price | $385 |
Good round-trip deal | $375 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 8, 2026.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 1/6
3:05 pm-8:50 pm
1 stop4h 45m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Thu 10/29
11:06 am-6:34 pm
1 stop6h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 11/1
6:25 pm-10:47 am
1 stop15h 22m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 4/6
6:00 am-10:13 am
1 stop27h 13m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$198
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 1/5
7:00 am-8:41 pm
2 stops12h 41m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 12/16
7:35 am-11:02 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
Quickest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 4/4
7:35 pm-10:58 pm
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
Green BayBoston
GRB Green Bay Austin-Straubel - BOS Boston Logan Intl
GRBBOS
Green Bay Austin-Straubel
Mon 11/9
1:30 pm-4:56 pm
Nonstop2h 26m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
Green BayBoston
GRB Green Bay Austin-Straubel - BOS Boston Logan Intl
GRBBOS
Green Bay Austin-Straubel
Sat 11/7
1:00 pm-4:30 pm
Nonstop2h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 4/5
5:55 am-3:03 pm
1 stop8h 08m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Wisconsin with our price prediction graph.
MKE-BOS
ATW-BOS
EAU-BOS
GRB-BOS
MSN-BOS
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 Wisconsin to Massachusetts
USWI-USMA
MKE-BOS
ATW-BOS
EAU-BOS
GRB-BOS
What is the cheapest month to book a flight from Wisconsin to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $307). Flying from Wisconsin to Massachusetts in February is currently the most expensive (average of $427). 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 WI to MA?
Find hourly flight availability from Wisconsin to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 8, 2026.
A simple way to save on the total cost of your ticket is to fly from Wisconsin to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Wisconsin to Massachusetts?
Airfare is below average for this route at the moment.
Wisconsin to Massachusetts flights typically cost between $291 and $478 in November.The cheapest round-trip price found within the last 5 days was $272 on Southwest (Nov 9-Nov 12).
How far ahead should I book a flight from Wisconsin to Massachusetts?
The best time to book flights from Wisconsin to Massachusetts is 88 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Wisconsin to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Massachusetts. Price data was last updated on October 3, 2026.
Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated October 8, 2026.
Read through reviews of airlines operating flights from Wisconsin to Massachusetts, such as Southwest,Delta, andUnited Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Wisconsin 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 Wisconsin 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 Wisconsin to Massachusetts by cabin class
Find flights from Wisconsin to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Massachusetts flights
Browse other Wisconsin and Massachusetts flight options. Last updated on October 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Wisconsin after your stay in Massachusetts
Wisconsin to Massachusetts flights
Consider these flights traveling from Wisconsin to Massachusetts.
Top 5 airlines flying from Wisconsin to Massachusetts
Discover the top 5 airlines that operate flights from Wisconsin to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$115 | Average$249 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$410 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$377 | FlexibilityNo cancel fee | On-time63% |