$103+ Cheap flights from Massachusetts to Wisconsin
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Sep 20 — Sep 271
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Wisconsin
Cheapest
Best
Last-minute
One-way
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 August 21, 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 August 21, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/17![Frontier logo]()
$176
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 9/212:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$177
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$183
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.
Sat 9/512:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/17![Frontier logo]()
$184
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.
Thu 10/111:17 am -
1 stop12h 42m
Sun 10/43:50 pm -
1 stop18h 01m
Deal found 8/16![Frontier logo]()
$186
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 9/1212:54 pm -
1 stop6h 29m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$187
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.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$193
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:11 am -
1 stop9h 57m
Fri 10/308:03 pm -
1 stop13h 06m
Deal found 8/17![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.
Fri 10/93:16 pm -
1 stop26h 31m
Wed 10/2110:51 am -
1 stop26h 30m
Deal found 8/17![Frontier logo]()
$230
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.
Thu 10/2910:11 am -
1 stop9h 57m
Sun 11/18:03 pm -
1 stop12h 13m
Deal found 8/16![Frontier logo]()
$238
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:11 am -
1 stop9h 57m
Sun 11/18:03 pm -
1 stop12h 13m
Deal found 8/17![Frontier logo]()
$248
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.
Thu 10/153:16 pm -
1 stop19h 40m
Sun 10/1810:51 am -
1 stop26h 30m
Deal found 8/18![Frontier logo]()
$249
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 August 21, 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 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.
Thu 9/1710:38 am -
Nonstop2h 51m
Sun 9/207:30 am -
Nonstop2h 31m
Deal found 8/17![United Airlines logo]()
$255
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.
Thu 9/38:50 pm -
Nonstop2h 54m
Sun 9/67:55 am -
Nonstop2h 29m
Deal found 8/18![Delta logo]()
$255
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.
Tue 9/228:30 am -
1 stop5h 30m
Wed 9/234:20 pm -
1 stop4h 50m
Deal found 8/17![Southwest logo]()
$275
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
1 stop6h 22m
Sat 10/242:35 pm -
1 stop8h 20m
Deal found 8/16![JetBlue logo]()
$309
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.
Sat 9/59:00 am -
Nonstop2h 59m
Mon 9/77:20 am -
Nonstop2h 34m
Deal found 8/20![United Airlines logo]()
$255
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.
Tue 10/137:30 am -
Nonstop2h 54m
Wed 10/143:05 pm -
Nonstop2h 39m
Deal found 8/18![Delta logo]()
$255
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 9/269:23 am -
Nonstop2h 52m
Tue 9/2910:25 am -
Nonstop2h 42m
Deal found 8/17![United Airlines logo]()
$255
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.
Fri 10/27:30 am -
Nonstop2h 54m
Sun 10/47:35 am -
Nonstop2h 33m
Deal found 8/16![Delta logo]()
$255
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.
Sat 9/125:30 am -
2 stops6h 35m
Mon 9/144:50 pm -
1 stop4h 45m
Deal found 8/18![Southwest logo]()
$307
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.
Thu 9/39:00 am -
Nonstop2h 59m
Sat 9/56:15 am -
Nonstop2h 21m
Deal found 8/20![United Airlines 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.
Tue 10/207:40 pm -
Nonstop2h 51m
Fri 10/237:25 am -
Nonstop2h 35m
Deal found 8/20![Delta logo]()
$255
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 9/39:00 am -
Nonstop2h 59m
Tue 9/87:55 pm -
Nonstop2h 35m
Deal found 8/18![United Airlines logo]()
$255
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 9/306:00 am -
1 stop5h 04m
Wed 10/76:35 pm -
Nonstop2h 27m
Deal found 8/16![Delta logo]()
$267
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.
Fri 10/165:50 am -
1 stop5h 55m
Mon 10/196:50 pm -
1 stop4h 15m
Deal found 8/16![Southwest logo]()
$327
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 8/285:07 pm -
1 stop7h 37m
Mon 8/315:27 pm -
1 stop5h 53m
Deal found 8/20![JetBlue logo]()
$375
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:50 pm -
Nonstop2h 42m
Sat 9/264:35 pm -
Nonstop2h 45m
Deal found 8/19![Delta logo]()
$275
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.
Fri 10/25:35 pm -
1 stop7h 35m
Tue 10/65:30 am -
2 stops7h 40m
Deal found 8/16![Southwest logo]()
$350
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.
Thu 9/179:15 am -
Nonstop2h 46m
Tue 9/227:15 am -
Nonstop2h 19m
Deal found 8/16![United Airlines logo]()
$317
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.
Sun 9/67:00 am -
1 stop6h 36m
Sat 9/122:35 pm -
Nonstop2h 32m
Deal found 8/17![Delta logo]()
$292
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.
Wed 11/117:45 am -
2 stops9h 15m
Sat 11/1412:25 pm -
2 stops8h 20m
Deal found 8/16![Southwest logo]()
$355
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.
Wed 11/1112:37 pm -
1 stop6h 18m
Sat 11/1410:42 am -
1 stop6h 36m
Deal found 8/19![United Airlines logo]()
$319
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.
Mon 9/214:15 pm -
Nonstop2h 37m
Tue 9/226:00 am -
1 stop5h 21m
Deal found 8/20![Delta logo]()
$292
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.
Mon 11/163:05 pm -
1 stop8h 50m
Sat 11/2110:15 am -
2 stops9h 25m
Deal found 8/17![Southwest logo]()
$363
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.
Wed 10/146:00 am -
2 stops7h 12m
Wed 10/216:00 am -
1 stop7h 29m
Deal found 8/20![United Airlines logo]()
$324
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:07 am -
Nonstop2h 46m
Wed 10/1410:36 am -
1 stop5h 54m
Deal found 8/19![Delta logo]()
$297
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.
Wed 12/97:00 am -
2 stops10h 00m
Mon 12/219:55 am -
1 stop4h 45m
Deal found 8/18![Southwest logo]()
$363
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.
Tue 9/156:10 am -
2 stops6h 53m
Sun 9/205:00 am -
1 stop4h 34m
Deal found 8/20![United Airlines logo]()
$324
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.
Tue 9/297:00 am -
Nonstop2h 56m
Tue 10/137:06 am -
Nonstop2h 44m
Deal found 8/16![Delta logo]()
$299
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 9/910:50 am -
2 stops8h 55m
Sat 9/125:30 am -
2 stops9h 20m
Deal found 8/19![Southwest logo]()
$367
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 9/166:00 am -
1 stop5h 24m
Wed 9/231:16 pm -
1 stop7h 14m
Deal found 8/17![United Airlines logo]()
$325
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated August 21, 2026 and is based on user searches.
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.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$193
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
1 stop8h 23m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/17![Frontier logo]()
$176
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$188
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 9/212:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$177
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$183
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.
Sat 9/512:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/17![Frontier logo]()
$184
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.
Sat 9/510:04 am -
1 stop26h 09m
Sat 9/1210:55 am -
Nonstop2h 14m
Deal found 8/18![Multiple Airlines logo]()
$263
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:30 am -
Nonstop2h 32m
Sat 9/1210:55 am -
Nonstop2h 14m
Deal found 8/17![JetBlue logo]()
$255
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:30 am -
Nonstop2h 32m
Wed 9/1610:55 am -
Nonstop2h 14m
Deal found 8/18![JetBlue logo]()
$264
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.
Sat 9/1212:54 pm -
1 stop6h 29m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/17![Frontier logo]()
$190
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.
Sat 9/198:30 am -
Nonstop2h 32m
Tue 9/2910:55 am -
Nonstop2h 14m
Deal found 8/18![JetBlue logo]()
$253
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.
Wed 9/309:15 am -
Nonstop2h 40m
Sat 10/32:35 pm -
Nonstop2h 32m
Deal found 8/17![Delta logo]()
$257
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 August 21, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. 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 8/20. 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 10/2112:57 pm -
1 stop6h 34m
Deal found 8/20![Frontier logo]()
$103
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.
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/19![Frontier logo]()
$104
This Faresmojo deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 pm -
Nonstop2h 54m
Deal found 8/21![JetBlue logo]()
$105
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:11 am -
1 stop14h 39m
Deal found 8/16![Frontier logo]()
$106
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/20![Frontier logo]()
$107
This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/21![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.
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$110
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.
Thu 9/1711:15 am -
1 stop28h 30m
Deal found 8/16![Multiple Airlines logo]()
$111
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:11 am -
1 stop9h 57m
Deal found 8/17![Frontier logo]()
$114
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:40 pm -
Nonstop2h 51m
Deal found 8/20![Delta logo]()
$114
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:04 am -
1 stop14h 04m
Deal found 8/17![Frontier logo]()
$115
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.
Fri 10/239:15 am -
1 stop10h 47m
Deal found 8/18![Frontier logo]()
$116
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Frontier) |
One-way from | $103 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $274 |
Good round-trip deal | $150 or less |
Good one-way deal | $198 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 August 21, 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
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 9/17
10:38 am-12:29 pm
Nonstop2h 51m
Chicago O'Hare Intl
Sun 9/20
7:30 am-11:01 am
Nonstop2h 31m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 9/3
8:50 pm-10:44 pm
Nonstop2h 54m
Chicago O'Hare Intl
Sun 9/6
7:55 am-11:24 am
Nonstop2h 29m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 9/5
9:00 am-10:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Mon 9/7
7:20 am-10:54 am
Nonstop2h 34m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/13
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 10/14
3:05 pm-6:44 pm
Nonstop2h 39m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 9/26
9:23 am-11:15 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 9/29
10:25 am-2:07 pm
Nonstop2h 42m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 10/2
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Sun 10/4
7:35 am-11:08 am
Nonstop2h 33m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 9/3
9:00 am-10:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Sat 9/5
6:15 am-9:36 am
Nonstop2h 21m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/20
7:40 pm-9:31 pm
Nonstop2h 51m
Chicago O'Hare Intl
Fri 10/23
7:25 am-11:00 am
Nonstop2h 35m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 9/3
9:00 am-10:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Tue 9/8
7:55 pm-11:30 pm
Nonstop2h 35m
$255
BostonMilwaukee
BOS Boston Logan Intl - MKE Milwaukee-Mitchell
BOSMKE
Boston Logan Intl
Wed 9/30
6:00 am-10:04 am
1 stop5h 04m
Milwaukee-Mitchell
Wed 10/7
6:35 pm-10:02 pm
Nonstop2h 27m
$267
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.
BOS-ORD
ALB-MSP
BDL-MKE
BOS-MKE
BDL-MSN
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
BOS-ORD
ALB-MSP
BDL-MKE
BOS-MKE
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 August 21, 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 at noon, which can drop the price by up to 5% versus a flight in the morning.
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 August 21, 2026.
The most flights from USMA to USWI are scheduled on a Monday (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 $204 and $378 in October.The cheapest round-trip price found within the last 5 days was $228 on Frontier (Oct 29-Oct 30).
How far ahead should I book a flight from Massachusetts to Wisconsin?
Booking 33 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 August 15, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Wednesday 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 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 August 21, 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.
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
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 August 21, 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$253 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$426 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$457 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$296 | FlexibilityNo cancel fee | On-time63% |