$100+ Cheap flights from Massachusetts to Wisconsin
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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Wisconsin 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 Massachusetts to WisconsinExplore the most affordable flight options available from Massachusetts to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Massachusetts to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/214:15 pm -
1 stop7h 02m
Wed 10/288:36 am -
1 stop5h 51m
Deal found 9/14![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/214:15 pm -
1 stop5h 28m
Tue 10/275:27 am -
2 stops9h 00m
Deal found 9/14![Delta logo]()
$214
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:39 pm -
1 stop7h 06m
Sun 11/88:15 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$216
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Thu 10/17:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/17![JetBlue logo]()
$217
This Frontier deal was found by Cheapflights users on 9/16. 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.
Fri 12/119:35 am -
1 stop11h 41m
Sun 12/139:21 pm -
1 stop10h 19m
Deal found 9/16![Frontier logo]()
$218
This KAYAK deal was found by Cheapflights users on 9/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:10 pm -
Nonstop2h 56m
Wed 11/47:25 am -
Nonstop2h 35m
Deal found 9/16![Delta logo]()
$219
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:47 am -
1 stop21h 04m
Mon 10/268:24 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/59:10 am -
1 stop4h 49m
Wed 10/710:05 am -
1 stop7h 23m
Deal found 9/16![Delta logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Fri 10/211:36 am -
1 stop12h 23m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/16![Multiple Airlines logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Fri 10/3012:39 pm -
1 stop7h 06m
Sat 10/318:24 pm -
Nonstop2h 44m
Deal found 9/17![Multiple Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/227:40 pm -
Nonstop2h 51m
Mon 10/265:29 pm -
1 stop5h 30m
Deal found 9/14![Delta logo]()
$225
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Wed 10/76:55 am -
Nonstop2h 54m
Fri 10/98:11 pm -
1 stop13h 51m
Deal found 9/15![Multiple Airlines logo]()
$226
Best flights from Massachusetts to WisconsinDiscover carefully curated flight deals from Massachusetts to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Massachusetts to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:08 pm -
1 stop7h 05m
Sun 12/67:00 am -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:45 am -
1 stop4h 53m
Sat 10/109:24 pm -
Nonstop2h 30m
Deal found 9/15![United Airlines logo]()
$252
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/54:10 pm -
1 stop6h 50m
Tue 10/67:05 am -
1 stop6h 24m
Deal found 9/16![JetBlue logo]()
$253
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/212:50 pm -
2 stops8h 35m
Wed 10/283:10 pm -
1 stop4h 55m
Deal found 9/13![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:15 pm -
1 stop7h 02m
Wed 10/217:00 am -
2 stops6h 58m
Deal found 9/15![Delta logo]()
$214
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:15 am -
1 stop4h 55m
Wed 9/238:45 am -
1 stop4h 42m
Deal found 9/14![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/214:15 pm -
2 stops8h 42m
Mon 10/2610:05 am -
1 stop4h 22m
Deal found 9/14![Delta logo]()
$214
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/27:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/14![JetBlue logo]()
$256
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/74:55 pm -
1 stop7h 04m
Tue 11/101:34 pm -
1 stop8h 56m
Deal found 9/16![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:59 pm -
1 stop5h 16m
Mon 10/57:35 am -
Nonstop2h 33m
Deal found 9/15![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 9/15. 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 10/236:35 pm -
1 stop5h 00m
Mon 10/265:50 pm -
1 stop4h 45m
Deal found 9/15![Southwest logo]()
$310
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:40 pm -
1 stop4h 52m
Tue 10/2011:06 am -
Nonstop2h 23m
Deal found 9/15![United Airlines logo]()
$287
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/176:55 am -
Nonstop2h 52m
Mon 10/196:10 am -
1 stop7h 19m
Deal found 9/13![JetBlue logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/176:00 am -
Nonstop2h 45m
Mon 10/266:25 pm -
Nonstop2h 22m
Deal found 9/16![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 12/74:08 pm -
2 stops8h 44m
Thu 12/107:00 am -
1 stop7h 07m
Deal found 9/16![Delta logo]()
$267
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/165:12 pm -
Nonstop3h 02m
Wed 10/2112:38 pm -
1 stop7h 11m
Deal found 9/12![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/304:25 pm -
2 stops8h 55m
Mon 11/25:30 am -
1 stop4h 40m
Deal found 9/14![Southwest logo]()
$331
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 1/79:45 am -
1 stop6h 32m
Sat 1/92:20 pm -
Nonstop2h 29m
Deal found 9/14![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:10 am -
1 stop8h 40m
Tue 10/273:15 pm -
1 stop6h 46m
Deal found 9/15![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 10/267:50 pm -
1 stop5h 00m
Thu 10/2912:20 pm -
1 stop5h 55m
Deal found 9/15![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/18:30 pm -
Nonstop2h 59m
Sun 10/47:29 am -
Nonstop2h 31m
Deal found 9/16![United Airlines logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/15. 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.
Thu 10/16:25 am -
1 stop4h 33m
Mon 10/53:00 pm -
1 stop7h 14m
Deal found 9/15![JetBlue logo]()
$335
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/304:10 pm -
1 stop5h 33m
Mon 11/210:05 am -
1 stop4h 22m
Deal found 9/16![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 11/55:00 am -
1 stop9h 55m
Sun 11/85:30 am -
1 stop4h 40m
Deal found 9/15![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/304:10 pm -
1 stop5h 33m
Tue 11/310:05 am -
1 stop4h 22m
Deal found 9/16![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/107:55 am -
1 stop7h 55m
Sun 11/1512:45 pm -
1 stop9h 25m
Deal found 9/14![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/56:20 am -
Nonstop2h 33m
Thu 10/87:30 am -
Nonstop2h 09m
Deal found 9/17![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/25:25 am -
1 stop5h 20m
Tue 10/62:20 pm -
2 stops7h 25m
Deal found 9/14![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 9/16. 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.
Sun 10/117:30 am -
Nonstop2h 54m
Tue 10/206:00 am -
1 stop4h 23m
Deal found 9/16![Delta logo]()
$293
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:23 am -
Nonstop2h 32m
Sun 10/1810:46 am -
Nonstop2h 13m
Deal found 9/14![JetBlue logo]()
$397
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated September 17, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Thu 10/17:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/17![JetBlue logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Fri 10/211:36 am -
1 stop12h 23m
Tue 10/68:24 pm -
Nonstop2h 59m
Deal found 9/16![Multiple Airlines logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Fri 10/211:36 am -
1 stop12h 23m
Mon 10/59:38 am -
Nonstop2h 28m
Deal found 9/15![Multiple Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/59:10 am -
1 stop4h 49m
Wed 10/710:05 am -
1 stop7h 23m
Deal found 9/16![Delta logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Wed 10/76:55 am -
Nonstop2h 54m
Fri 10/98:11 pm -
1 stop13h 51m
Deal found 9/15![Multiple Airlines logo]()
$226
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/165:12 pm -
Nonstop3h 02m
Mon 10/196:10 am -
1 stop7h 19m
Deal found 9/14![JetBlue logo]()
$229
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/209:23 am -
Nonstop2h 52m
Tue 10/279:13 am -
Nonstop2h 33m
Deal found 9/17![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/214:15 pm -
1 stop7h 02m
Wed 10/288:36 am -
1 stop5h 51m
Deal found 9/14![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/214:15 pm -
1 stop5h 28m
Tue 10/275:27 am -
2 stops9h 00m
Deal found 9/14![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/227:40 pm -
Nonstop2h 51m
Mon 10/265:29 pm -
1 stop5h 30m
Deal found 9/14![Delta logo]()
$225
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:47 am -
1 stop21h 04m
Mon 10/268:24 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$221
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Fri 10/3012:39 pm -
1 stop7h 06m
Sat 10/318:24 pm -
Nonstop2h 44m
Deal found 9/17![Multiple Airlines logo]()
$224
One-way flights from Massachusetts to WisconsinSearch for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/264:10 pm -
1 stop7h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$100
This Frontier deal was found by Cheapflights users on 9/16. 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.
Fri 12/119:35 am -
1 stop11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/271:25 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$118
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 12/1710:00 am -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 12/154:45 pm -
Nonstop2h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$119
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 12/112:40 pm -
Nonstop3h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$119
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:30 am -
Nonstop2h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$120
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/166:43 pm -
Nonstop2h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$121
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/135:35 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$123
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/265:15 am -
1 stop5h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$124
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/206:45 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$126
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:54 pm -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$127
Find flight deals from Massachusetts to Wisconsin
Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Delta) |
One-way from | $100 (Delta) |
Popular in | November |
Cheapest in | May |
Average price | $317 |
Good round-trip deal | $257 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Wisconsin 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 17, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Sun 12/6
4:08 pm-10:13 pm
1 stop7h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Thu 10/22
4:15 pm-10:17 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
HartfordMinneapolis
BDL Hartford Bradley Intl - MSP Minneapolis St Paul
BDLMSP
Hartford Bradley Intl
Sat 10/31
8:10 am-2:25 pm
1 stop7h 15m
Minneapolis St Paul
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 11/12
7:00 am-1:08 pm
1 stop7h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
HartfordMinneapolis
BDL Hartford Bradley Intl - MSP Minneapolis St Paul
BDLMSP
Hartford Bradley Intl
Sat 11/14
8:40 am-4:35 pm
2 stops8h 55m
Minneapolis St Paul
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
AlbanyChicago
ALB Albany Intl - ORD Chicago O'Hare Intl
ALBORD
Albany Intl
Tue 10/13
7:06 pm-11:57 pm
1 stop5h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
HartfordMinneapolis
BDL Hartford Bradley Intl - MSP Minneapolis St Paul
BDLMSP
Hartford Bradley Intl
Thu 10/29
5:50 am-12:00 pm
1 stop7h 10m
Minneapolis St Paul
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 12/16
7:55 am-12:00 pm
1 stop5h 05m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
HartfordMilwaukee
BDL Hartford Bradley Intl - MKE Milwaukee-Mitchell
BDLMKE
Hartford Bradley Intl
Sat 10/10
5:14 pm-8:06 pm
1 stop3h 52m
Milwaukee-Mitchell
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
BostonMinneapolis
BOS Boston Logan Intl - MSP Minneapolis St Paul
BOSMSP
Boston Logan Intl
Mon 11/9
7:30 pm-12:45 am
1 stop6h 15m
Minneapolis St Paul
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Massachusetts with our price prediction graph.
ORH-ORD
BDL-MSP
BOS-ORD
BOS-MSP
ALB-ORD
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 Massachusetts to Wisconsin
USMA-USWI
ORH-ORD
BDL-MSP
BOS-ORD
BOS-MSP
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $314). Flying from Massachusetts to Wisconsin in April is currently the most expensive (average of $451). 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 MA to WI?
Find hourly flight availability from Massachusetts to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2026.
When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 7% versus a flight in the afternoon.
Weekly flight availability from Massachusetts to Wisconsin
Explore weekly flight availability from Massachusetts to Wisconsin. 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 September 17, 2026.
The most flights from USMA to USWI are scheduled on a Wednesday (8 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 Massachusetts to Wisconsin?
Airfare is typical for this route at the moment.
Massachusetts to Wisconsin flights typically cost between $203 and $437 in October.The cheapest round-trip price found within the last 5 days was $252 on Southwest (Oct 14-Nov 4).
How far ahead should I book a flight from Massachusetts to Wisconsin?
Booking 66 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Wisconsin. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Massachusetts to Wisconsin?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Wisconsin. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated September 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Wisconsin. 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 Massachusetts to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Wisconsin by cabin class
Find flights from Massachusetts to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Wisconsin flights
Browse other Massachusetts and Wisconsin flight options. Last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Wisconsin
Find the right flight back to Massachusetts after your stay in Wisconsin
Massachusetts to Wisconsin flights
Consider these flights traveling from Massachusetts to Wisconsin.
Top 5 airlines flying from Massachusetts to Wisconsin
Discover the top 5 airlines that operate flights from Massachusetts to Wisconsin. 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$263 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$124 | Average$431 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$457 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$311 | FlexibilityNo cancel fee | On-time63% |