$90+ Cheap flights from Wisconsin 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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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 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 August 21, 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 August 21, 2026.
This Frontier deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/16![Frontier logo]()
$176
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/18![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Wed 10/2812:39 pm -
1 stop8h 05m
Deal found 8/19![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$187
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/610:04 am -
1 stop14h 04m
Deal found 8/16![Frontier logo]()
$197
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:03 pm -
1 stop12h 13m
Mon 11/1610:11 am -
1 stop9h 57m
Deal found 8/19![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:51 am -
1 stop26h 30m
Sun 10/113:16 pm -
1 stop19h 40m
Deal found 8/17![Frontier logo]()
$230
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:15 am -
1 stop23h 47m
Thu 11/510:11 am -
1 stop9h 57m
Deal found 8/17![Frontier logo]()
$248
This CheapOair deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:51 am -
1 stop26h 30m
Sun 10/253:16 pm -
1 stop19h 40m
Deal found 8/15![Frontier logo]()
$250
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:55 am -
Nonstop2h 14m
Sat 10/311:26 am -
1 stop22h 56m
Deal found 8/16![Multiple Airlines logo]()
$253
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 August 21, 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 August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:30 am -
Nonstop2h 31m
Sun 9/206:00 am -
Nonstop2h 59m
Deal found 8/17![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:38 am -
Nonstop2h 28m
Sun 10/186:55 am -
Nonstop2h 51m
Deal found 8/15![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:19 pm -
Nonstop2h 40m
Sun 9/67:30 am -
Nonstop2h 56m
Deal found 8/20![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:00 pm -
2 stops7h 45m
Tue 9/294:55 pm -
1 stop5h 05m
Deal found 8/19![Southwest logo]()
$332
This KAYAK deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:48 am -
Nonstop2h 20m
Tue 9/18:13 pm -
Nonstop2h 47m
Deal found 8/20![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:15 am -
Nonstop2h 09m
Mon 9/214:53 pm -
Nonstop2h 37m
Deal found 8/18![United Airlines logo]()
$257
This JetBlue deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:24 pm -
Nonstop2h 59m
Wed 10/143:55 pm -
1 stop8h 49m
Deal found 8/17![JetBlue logo]()
$258
This KAYAK deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:29 am -
Nonstop2h 36m
Thu 9/108:50 pm -
Nonstop2h 42m
Deal found 8/15![Delta logo]()
$271
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:35 pm -
1 stop8h 50m
Fri 10/235:35 am -
1 stop9h 04m
Deal found 8/15![JetBlue logo]()
$261
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:59 am -
Nonstop2h 05m
Mon 9/287:35 pm -
1 stop4h 57m
Deal found 8/20![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:30 am -
Nonstop2h 29m
Sun 9/65:51 am -
1 stop6h 46m
Deal found 8/20![Delta logo]()
$285
This JetBlue deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:00 pm -
1 stop7h 39m
Thu 10/224:00 pm -
1 stop6h 56m
Deal found 8/17![JetBlue logo]()
$265
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:05 pm -
2 stops7h 00m
Tue 11/32:35 pm -
2 stops8h 45m
Deal found 8/15![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:55 am -
Nonstop2h 29m
Wed 9/24:16 pm -
Nonstop3h 04m
Deal found 8/18![Delta logo]()
$296
This JetBlue deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:38 am -
Nonstop2h 28m
Sun 10/2511:15 am -
Nonstop3h 05m
Deal found 8/20![JetBlue logo]()
$275
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:55 am -
1 stop4h 15m
Thu 10/225:35 am -
1 stop6h 05m
Deal found 8/17![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:05 am -
1 stop7h 16m
Wed 10/217:55 am -
1 stop6h 44m
Deal found 8/18![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:30 am -
Nonstop2h 29m
Sun 9/67:30 am -
Nonstop2h 56m
Deal found 8/20![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:55 pm -
1 stop6h 04m
Sat 9/193:16 pm -
1 stop4h 49m
Deal found 8/16![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:55 pm -
1 stop7h 20m
Thu 9/105:25 am -
1 stop5h 50m
Deal found 8/16![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:15 am -
Nonstop2h 38m
Sat 11/142:45 pm -
Nonstop3h 07m
Deal found 8/17![Delta logo]()
$299
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:00 pm -
1 stop7h 14m
Fri 10/27:00 am -
1 stop7h 45m
Deal found 8/19![JetBlue logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:00 am -
Nonstop2h 18m
Sat 10/315:02 pm -
Nonstop2h 48m
Deal found 8/16![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/87:00 am -
1 stop6h 38m
Deal found 8/18![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
2 stops8h 55m
Sat 9/512:10 pm -
2 stops7h 55m
Deal found 8/19![Southwest logo]()
$372
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:00 pm -
1 stop7h 14m
Fri 10/27:00 am -
1 stop7h 45m
Deal found 8/19![JetBlue logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:06 am -
Nonstop2h 23m
Tue 10/279:37 am -
Nonstop2h 52m
Deal found 8/16![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:05 am -
1 stop4h 36m
Sun 9/277:00 am -
Nonstop2h 56m
Deal found 8/16![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:30 am -
Nonstop2h 09m
Sun 10/186:20 am -
Nonstop2h 33m
Deal found 8/19![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:00 am -
2 stops8h 05m
Sun 11/15:30 am -
2 stops11h 00m
Deal found 8/18![Southwest logo]()
$401
Last-minute flights from Wisconsin to MassachusettsDiscover last-minute flight deals from Wisconsin to Massachusetts. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Massachusetts. Data last updated August 21, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/16![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/610:04 am -
1 stop14h 04m
Deal found 8/16![Frontier logo]()
$197
This Super.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/18![Frontier logo]()
$183
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:59 am -
Nonstop2h 05m
Tue 9/158:10 am -
Nonstop2h 34m
Deal found 8/17![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:00 pm -
Nonstop2h 18m
Mon 9/146:36 pm -
Nonstop2h 54m
Deal found 8/18![American Airlines logo]()
$258
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$198
This Trip.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:11 am -
1 stop26h 14m
Sun 9/2011:15 am -
1 stop28h 30m
Deal found 8/20![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:11 am -
1 stop26h 14m
Mon 9/288:18 pm -
2 stops27h 41m
Deal found 8/17![Multiple Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:10 pm -
Nonstop2h 12m
Tue 10/610:00 am -
1 stop5h 26m
Deal found 8/17![United Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:10 am -
Nonstop2h 20m
Mon 9/286:36 pm -
Nonstop2h 54m
Deal found 8/16![American Airlines logo]()
$268
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 August 21, 2026.
Search for one-way flight options from Wisconsin to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 am -
1 stop26h 16m
Deal found 8/17![Multiple Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:11 am -
1 stop26h 14m
Deal found 8/17![Multiple Airlines logo]()
$93
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop14h 10m
Deal found 8/16![Frontier logo]()
$97
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/19![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/19![Frontier logo]()
$102
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/43:50 pm -
1 stop18h 01m
Deal found 8/19![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
1 stop25h 18m
Deal found 8/16![Multiple Airlines logo]()
$106
This CheapOair deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/17![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:56 pm -
2 stops21h 02m
Deal found 8/18![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
1 stop26h 01m
Deal found 8/19![Multiple Airlines logo]()
$108
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:44 pm -
1 stop16h 25m
Deal found 8/18![Frontier logo]()
$109
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Frontier) |
One-way from | $90 (Kiwi.com) |
Popular in | February |
Cheapest in | May |
Average price | $269 |
Good round-trip deal | $176 or less |
Good one-way deal | $134 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 August 21, 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
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/19
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sun 9/20
6:00 am-7:59 am
Nonstop2h 59m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 10/14
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Sun 10/18
6:55 am-8:46 am
Nonstop2h 51m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 9/3
3:19 pm-6:59 pm
Nonstop2h 40m
Boston Logan Intl
Sun 9/6
7:30 am-9:26 am
Nonstop2h 56m
$256
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Thu 9/17
7:15 am-10:24 am
Nonstop2h 09m
Albany Intl
Mon 9/21
4:53 pm-6:30 pm
Nonstop2h 37m
$257
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/6
8:24 pm-12:23 am
Nonstop2h 59m
Boston Logan Intl
Wed 10/14
3:55 pm-11:44 pm
1 stop8h 49m
$258
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/17
2:35 pm-12:25 am
1 stop8h 50m
Boston Logan Intl
Fri 10/23
5:35 am-1:39 pm
1 stop9h 04m
$261
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/19
3:00 pm-11:39 pm
1 stop7h 39m
Boston Logan Intl
Thu 10/22
4:00 pm-9:56 pm
1 stop6h 56m
$265
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Mon 9/21
11:59 am-3:04 pm
Nonstop2h 05m
Albany Intl
Mon 9/28
7:35 pm-11:32 pm
1 stop4h 57m
$267
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 9/9
10:29 am-2:05 pm
Nonstop2h 36m
Boston Logan Intl
Thu 9/10
8:50 pm-10:32 pm
Nonstop2h 42m
$271
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 10/16
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Sun 10/25
11:15 am-1:20 pm
Nonstop3h 05m
$275
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.
ORD-BOS
MSP-ALB
ORD-ALB
MSP-BOS
MSN-BDL
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
ORD-BOS
MSP-ALB
ORD-ALB
MSP-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 $306). 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 August 21, 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 23% on your trip compared to booking a flight at noon.
Weekly flight availability from Wisconsin to Massachusetts
Explore weekly flight availability from Wisconsin 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 August 21, 2026.
The most flights from USWI to USMA are scheduled on a Wednesday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Wisconsin to Massachusetts?
Airfare is typical for this route at the moment.
Wisconsin to Massachusetts flights typically cost between $218 and $339 in November.The cheapest round-trip price found within the last 5 days was $228 on Frontier (Nov 12-Nov 16).
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 August 15, 2026.
Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated August 21, 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
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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 August 21, 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$244 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$110 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$409 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$332 | FlexibilityNo cancel fee | On-time63% |