$70+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 19 — May 261
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Wisconsin with Cheapflights
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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 April 19, 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 April 19, 2026.
This Expedia deal was found by Cheapflights users on 4/16. 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.
Mon 5/116:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Wed 5/1312:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/16![Frontier logo]()
$140
This SmartFares deal was found by Cheapflights users on 4/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 16m
JetBlue
Deal found 4/17![JetBlue logo]()
$150
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/15. 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 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/81:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$151
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/96:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/128:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 4/18![American Airlines logo]()
$153
This Priceline deal was found by Cheapflights users on 4/16. 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.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/268:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$154
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/131:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/15![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/15![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Sat 5/29:16 am
ORD
- BOS
1 stop15h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$163
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 April 19, 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 April 19, 2026.
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/233:08 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Wed 5/279:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/15![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 4/17. 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 6/27:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Tue 6/97:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/17![Delta logo]()
$167
This JetBlue deal was found by Cheapflights users on 4/17. 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 5/22:44 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Wed 5/64:58 pm
MKE
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/17![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/14. 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 7/167:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 7/226:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/14![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 4/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:18 pm
BOS
- GRB
2 stops7h 13m
American Airlines
Sat 5/27:30 am
GRB
- BOS
1 stop6h 48m
American Airlines
Deal found 4/19![American Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 6/167:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 6/207:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/18![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 4/14. 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.
Sat 5/95:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/107:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/14![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 4/14. 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 5/1912:50 pm
BDL
- MKE
2 stops9h 55m
Southwest
Fri 5/224:50 pm
MKE
- BDL
1 stop4h 15m
Southwest
Deal found 4/14![Southwest logo]()
$392
This Sun Country Air deal was found by Cheapflights users on 4/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:35 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Wed 6/106:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 4/19![Sun Country Air logo]()
$394
This Delta deal was found by Cheapflights users on 4/16. 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.
Sat 5/27:00 am
BOS
- MKE
1 stop5h 10m
Delta
Wed 5/67:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/16![Delta logo]()
$197
This JetBlue deal was found by Cheapflights users on 4/17. 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 4/287:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Wed 4/299:41 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/17![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/16. 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 7/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sat 7/113:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/16![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 4/17. 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.
Fri 4/244:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Tue 5/56:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 4/17![Delta logo]()
$202
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Fri 5/88:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Sun 5/107:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/18![United Airlines logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Tue 5/56:39 pm
BOS
- ORD
Nonstop3h 01m
United Airlines
Sun 5/105:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Deal found 4/18![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 4/14. 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.
Fri 5/14:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Sun 5/36:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 4/14![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/215:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 5/256:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/14![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 4/15. 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.
Fri 7/179:10 am
BOS
- MKE
Nonstop2h 44m
Delta
Mon 7/206:40 pm
MKE
- BOS
1 stop4h 19m
Delta
Deal found 4/15![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 4/18. 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.
Fri 6/125:30 am
BOS
- MKE
1 stop4h 21m
Delta
Wed 6/245:56 pm
MKE
- BOS
1 stop4h 31m
Delta
Deal found 4/18![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 4/19. 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.
Thu 8/1310:15 am
ALB
- MSP
1 stop5h 45m
Southwest
Mon 8/175:45 am
MSP
- ALB
1 stop4h 25m
Southwest
Deal found 4/19![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 4/14. 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.
Thu 6/412:40 pm
BDL
- MKE
2 stops10h 05m
Southwest
Fri 6/55:50 am
MKE
- BDL
2 stops7h 20m
Southwest
Deal found 4/14![Southwest logo]()
$411
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sun 7/126:00 am
BOS
- MKE
1 stop6h 14m
United Airlines
Wed 7/1510:39 am
MKE
- BOS
1 stop4h 50m
United Airlines
Deal found 4/16![United Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 4/14. 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 4/309:06 am
BOS
- MKE
1 stop5h 28m
Delta
Sun 5/37:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/14![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 4/17. 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 6/75:35 am
BDL
- MKE
2 stops6h 10m
Southwest
Wed 6/106:45 am
MKE
- BDL
1 stop6h 15m
Southwest
Deal found 4/17![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Fri 5/227:19 am
BOS
- MKE
1 stop4h 49m
United Airlines
Sun 5/247:00 pm
MKE
- BOS
1 stop4h 59m
United Airlines
Deal found 4/15![United Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 4/18. 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 7/33:00 pm
ALB
- MSP
2 stops9h 15m
Southwest
Wed 7/85:25 am
MSP
- ALB
2 stops8h 00m
Southwest
Deal found 4/18![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 4/16. 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 4/307:30 am
BOS
- MKE
1 stop6h 41m
United Airlines
Sun 5/36:56 pm
MKE
- BOS
1 stop5h 03m
United Airlines
Deal found 4/16![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 4/15. 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 5/185:40 am
BOS
- MSP
1 stop5h 20m
Southwest
Fri 5/224:55 pm
MSP
- BOS
1 stop5h 20m
Southwest
Deal found 4/15![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 4/18. 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.
Sat 6/65:51 am
BOS
- GRB
1 stop6h 22m
Delta
Mon 6/86:00 pm
GRB
- BOS
1 stop4h 54m
Delta
Deal found 4/18![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 4/18. 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 5/96:00 am
BOS
- MKE
1 stop4h 45m
United Airlines
Tue 5/121:46 pm
MKE
- BOS
1 stop7h 13m
United Airlines
Deal found 4/18![United Airlines logo]()
$267
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Sat 5/29:16 am
ORD
- BOS
1 stop15h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$163
This Expedia deal was found by Cheapflights users on 4/16. 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.
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/16![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/15. 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 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/81:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$151
This SmartFares deal was found by Cheapflights users on 4/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 16m
JetBlue
Deal found 4/17![JetBlue logo]()
$150
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 5/96:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/128:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 4/18![American Airlines logo]()
$153
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/131:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/16. 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.
Mon 5/116:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Wed 5/1312:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/16![Frontier logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/15![JetBlue logo]()
$162
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$151
This Priceline deal was found by Cheapflights users on 4/16. 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.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/268:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$154
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 April 19, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 19, 2026.
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/14![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/14![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$79
This Orbitz deal was found by Cheapflights users on 4/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/17![Frontier logo]()
$80
This CheapOair deal was found by Cheapflights users on 4/15. 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.
Sat 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Deal found 4/15![Frontier logo]()
$82
This KAYAK deal was found by Cheapflights users on 4/14. 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.
Tue 7/145:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 4/14![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 4/16![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 4/17. 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.
Sat 5/165:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 4/17![Delta logo]()
$84
This Super.com deal was found by Cheapflights users on 4/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/14![JetBlue logo]()
$86
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:25 am
BOS
- ORD
1 stop13h 14m
Frontier
Deal found 4/15![Frontier logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/16![JetBlue logo]()
$88
This Super.com deal was found by Cheapflights users on 4/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/17![Frontier logo]()
$89
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 April 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Expedia) |
One-way from | $70 (Priceline) |
Popular in | November |
Cheapest in | September |
Average price | $439 |
Good round-trip deal | $158 or less |
Good one-way deal | $128 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 2,558,603 searches. Data last updated April 19, 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 - ORD
BOSORD
Boston Logan Intl
Sat 5/23
3:08 pm-5:00 pm
Nonstop2h 52m
Chicago O'Hare Intl
Wed 5/27
9:26 pm-12:59 am
Nonstop2h 33m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 6/9
7:10 am-10:46 am
Nonstop2h 36m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/16
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 7/22
6:15 am-9:39 am
Nonstop2h 24m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/16
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 6/20
7:40 pm-11:16 pm
Nonstop2h 36m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sat 7/11
3:55 pm-7:30 pm
Nonstop2h 35m
$182
Quickest round-trip
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Sat 5/2
2:44 pm-4:20 pm
Nonstop2h 36m
Milwaukee-Mitchell
Wed 5/6
4:58 pm-8:15 pm
Nonstop2h 17m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/8
8:25 pm-10:20 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sun 5/10
7:30 am-11:01 am
Nonstop2h 31m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/9
5:30 pm-7:33 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 5/10
7:00 am-10:35 am
Nonstop2h 35m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/5
6:39 pm-8:40 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sun 5/10
5:00 am-10:20 am
1 stop4h 20m
$192
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Sat 5/2
7:00 am-11:10 am
1 stop5h 10m
Milwaukee-Mitchell
Wed 5/6
7:58 pm-11:21 pm
Nonstop2h 23m
$197
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
BOS-MKE
BDL-MSP
BOS-GRB
ALB-MSP
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
BOS-MKE
BDL-MSP
BOS-GRB
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, August is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $78). Flying from Massachusetts to Wisconsin in March is currently the most expensive (average of $207). 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 April 19, 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 37% versus a flight in the morning.
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 April 18, 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. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Massachusetts to Wisconsin?
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 April 19, 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
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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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 April 19, 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 2,558,603 searches. Data last updated April 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$270 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$271 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$455 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$440 | FlexibilityNo cancel fee | On-time71% |