$88+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jul 21 — Jul 281
Round-trip
1 adult, Economy
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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 June 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 June 21, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 6/20![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 7/83:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Thu 7/97:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/18![United Airlines logo]()
$178
This Delta deal was found by Cheapflights users on 6/19. 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.
Thu 7/97:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Sat 7/116:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/19![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 6/17. 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 7/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Wed 7/156:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/17![Delta logo]()
$180
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Thu 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/20![JetBlue logo]()
$181
This Delta deal was found by Cheapflights users on 6/19. 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.
Wed 8/264:16 pm
BOS
- ORD
Nonstop3h 04m
Delta
Fri 9/47:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/19![Delta logo]()
$182
This Delta deal was found by Cheapflights users on 6/19. 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.
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 7/303:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 6/19![Delta logo]()
$183
This Super.com deal was found by Cheapflights users on 6/16. 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.
Tue 7/75:25 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 7/86:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 6/16![JetBlue logo]()
$184
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Fri 8/215:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/236:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 6/17![United Airlines logo]()
$185
This Super.com deal was found by Cheapflights users on 6/17. 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.
Sat 7/44:43 pm
BOS
- ORD
1 stop5h 47m
JetBlue
Thu 7/96:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/17![JetBlue logo]()
$186
This Delta deal was found by Cheapflights users on 6/19. 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.
Thu 7/97:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Fri 7/107:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 6/19![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 6/17. 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 7/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Fri 7/1010:28 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/17![Delta logo]()
$188
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 June 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 June 21, 2026.
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Tue 7/216:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 6/20![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 6/16. 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 8/107:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Wed 8/1210:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/16![Delta logo]()
$188
This JetBlue deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Mon 9/286:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 6/19![JetBlue logo]()
$201
This KAYAK deal was found by Cheapflights users on 6/16. 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.
Mon 7/136:30 pm
BOS
- ORD
Nonstop3h 29m
American Airlines
Wed 7/1511:00 am
ORD
- BOS
Nonstop2h 38m
American Airlines
Deal found 6/16![American Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 6/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:30 am
ALB
- MSP
1 stop6h 55m
Southwest
Tue 8/256:15 am
MSP
- ALB
2 stops7h 05m
Southwest
Deal found 6/20![Southwest logo]()
$322
This Sun Country Air deal was found by Cheapflights users on 6/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2111:40 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Fri 7/245:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$358
This United Airlines deal was found by Cheapflights users on 6/18. 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 8/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/239:40 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 6/18![United Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 6/19. 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.
Thu 7/308:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 8/137:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/19![Delta logo]()
$191
This JetBlue deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:43 pm
BOS
- ORD
1 stop5h 47m
JetBlue
Thu 7/96:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/19![JetBlue logo]()
$220
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:30 am
BOS
- ORD
Nonstop3h 03m
Delta
Fri 11/63:00 pm
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/20![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/18. 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 10/296:00 am
BOS
- ORD
1 stop4h 37m
United Airlines
Sun 11/19:30 pm
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 6/18![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Sat 9/121:19 pm
MKE
- BOS
1 stop5h 04m
Delta
Deal found 6/18![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/306:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 6/16![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 6/18. 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 7/1712:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Mon 7/203:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 6/18![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 6/16. 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 7/138:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 7/156:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/16![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 6/15. 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 8/275:05 pm
ALB
- MSP
1 stop5h 15m
Southwest
Wed 9/26:15 am
MSP
- ALB
2 stops7h 05m
Southwest
Deal found 6/15![Southwest logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:56 pm
ALB
- MSP
1 stop5h 26m
American Airlines
Tue 8/116:00 am
MSP
- ALB
1 stop7h 44m
American Airlines
Deal found 6/15![American Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 6/18. 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.
Mon 7/135:30 am
BOS
- MKE
1 stop4h 09m
Delta
Tue 7/146:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 6/18![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/20. 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 8/296:00 am
BOS
- MKE
3 stops12h 25m
United Airlines
Tue 9/16:15 am
MKE
- BOS
2 stops7h 35m
United Airlines
Deal found 6/20![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:56 pm
ALB
- MSP
1 stop5h 26m
American Airlines
Mon 8/36:30 am
MSP
- ALB
1 stop7h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 6/17. 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.
Wed 7/294:15 pm
ALB
- MSP
2 stops8h 40m
Southwest
Wed 8/56:15 am
MSP
- ALB
1 stop4h 20m
Southwest
Deal found 6/17![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 6/19. 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.
Sat 7/1111:40 am
BOS
- MKE
Nonstop2h 35m
Delta
Sat 7/184:57 pm
MKE
- BOS
1 stop6h 02m
Delta
Deal found 6/19![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am
BOS
- MKE
1 stop5h 00m
United Airlines
Sat 10/36:32 pm
MKE
- BOS
1 stop5h 27m
United Airlines
Deal found 6/16![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:15 am
BOS
- MKE
Nonstop2h 40m
Delta
Sun 9/208:11 am
MKE
- BOS
1 stop5h 41m
Delta
Deal found 6/18![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 6/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:25 am
BOS
- MSP
2 stops7h 20m
Southwest
Fri 7/245:40 pm
MSP
- BOS
1 stop4h 50m
Southwest
Deal found 6/20![Southwest logo]()
$373
This JetBlue deal was found by Cheapflights users on 6/20. 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.
Sat 8/294:45 pm
ORH
- ORD
1 stop7h 59m
JetBlue
Tue 9/17:00 am
ORD
- ORH
1 stop7h 50m
JetBlue
Deal found 6/20![JetBlue logo]()
$412
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:24 pm
BDL
- MSN
1 stop5h 00m
American Airlines
Sun 9/205:00 am
MSN
- BDL
1 stop6h 08m
American Airlines
Deal found 6/20![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:18 pm
ORH
- ORD
1 stop4h 57m
Delta
Sun 10/257:00 am
ORD
- ORH
1 stop6h 37m
Delta
Deal found 6/20![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 6/18. 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 8/213:36 pm
BDL
- MSP
1 stop9h 22m
United Airlines
Sat 8/228:00 am
MSP
- BDL
1 stop5h 29m
United Airlines
Deal found 6/18![United Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 8/46:20 pm
ALB
- MSP
1 stop4h 40m
Southwest
Tue 8/1112:25 pm
MSP
- ALB
2 stops7h 35m
Southwest
Deal found 6/15![Southwest logo]()
$387
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated June 21, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/19. 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 6/2611:18 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 6/286:40 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 6/19![Sun Country Air logo]()
$196
This JetBlue deal was found by Cheapflights users on 6/15. 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.
Mon 6/298:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 7/89:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Deal found 6/15![JetBlue logo]()
$199
This Super.com deal was found by Cheapflights users on 6/16. 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.
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 7/79:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Deal found 6/16![JetBlue logo]()
$183
This JetBlue deal was found by Cheapflights users on 6/15. 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.
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 7/89:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 6/15![JetBlue logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Fri 7/38:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/16![JetBlue logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/87:19 am
BOS
- MKE
1 stop6h 29m
United Airlines
Wed 7/157:23 pm
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 6/20![United Airlines logo]()
$197
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:16 pm
ORH
- ORD
1 stop8h 25m
American Airlines
Mon 7/136:37 am
ORD
- ORH
1 stop9h 14m
American Airlines
Deal found 6/20![American Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/167:19 am
BOS
- MKE
1 stop6h 29m
United Airlines
Sat 7/185:29 pm
MKE
- BOS
1 stop4h 52m
United Airlines
Deal found 6/19![United Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:16 pm
ORH
- ORD
1 stop16h 54m
American Airlines
Mon 7/276:37 am
ORD
- ORH
1 stop9h 14m
American Airlines
Deal found 6/20![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 6/17. 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 7/215:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Tue 7/289:30 am
ORD
- ORH
1 stop6h 30m
Delta
Deal found 6/17![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/2210:49 am
BOS
- MKE
1 stop7h 28m
American Airlines
Wed 7/2912:52 pm
MKE
- BOS
1 stop7h 18m
American Airlines
Deal found 6/19![American Airlines logo]()
$196
This Sun Country Air deal was found by Cheapflights users on 6/19. 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.
Fri 7/246:31 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 8/26:55 am
MSP
- BDL
Nonstop2h 34m
Sun Country Air
Deal found 6/19![Sun Country Air logo]()
$198
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 June 21, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This Super.com deal was found by Cheapflights users on 6/19. 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 7/36:41 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 6/19![Sun Country Air logo]()
$88
This Sun Country Air deal was found by Cheapflights users on 6/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:22 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 8/148:02 pm
ALB
- ORD
1 stop17h 13m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:53 pm
ALB
- ORD
1 stop17h 22m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$94
This Delta deal was found by Cheapflights users on 6/17. 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 7/145:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 6/17![Delta logo]()
$94
This Super.com deal was found by Cheapflights users on 6/16. 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.
Mon 9/75:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
Deal found 6/16![JetBlue logo]()
$95
This Delta deal was found by Cheapflights users on 6/17. 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 7/17:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 6/17![Delta logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/16![JetBlue logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 6/2611:18 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 6/20![Sun Country Air logo]()
$98
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:16 pm
ORH
- ORD
1 stop7h 14m
American Airlines
Deal found 6/17![American Airlines logo]()
$98
This United Airlines deal was found by Cheapflights users on 6/17. 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 8/156:00 pm
BOS
- ORD
1 stop6h 22m
United Airlines
Deal found 6/17![United Airlines logo]()
$98
This Sun Country Air deal was found by Cheapflights users on 6/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:41 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$99
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Cheapflightsfares) |
One-way from | $88 (Super.com) |
Popular in | November |
Cheapest in | September |
Average price | $286 |
Good round-trip deal | $179 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 June 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 - ORD
BOSORD
Boston Logan Intl
Mon 7/20
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Tue 7/21
6:00 am-11:16 am
1 stop4h 16m
$180
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/20
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 8/23
9:40 pm-1:15 am
Nonstop2h 35m
$181
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 8/10
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 8/12
10:30 am-1:59 pm
Nonstop2h 29m
$188
Quickest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/30
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Thu 8/13
7:30 pm-11:00 pm
Nonstop2h 30m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/26
4:00 pm-10:06 pm
1 stop7h 06m
Chicago O'Hare Intl
Mon 9/28
6:30 am-2:40 pm
1 stop7h 10m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 11/5
7:30 am-9:33 am
Nonstop3h 03m
Chicago O'Hare Intl
Fri 11/6
3:00 pm-6:31 pm
Nonstop2h 31m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 10/29
6:00 am-9:37 am
1 stop4h 37m
Chicago O'Hare Intl
Sun 11/1
9:30 pm-1:02 am
Nonstop2h 32m
$217
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 9/9
9:15 am-10:55 am
Nonstop2h 40m
Milwaukee-Mitchell
Sat 9/12
1:19 pm-7:23 pm
1 stop5h 04m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/17
12:25 pm-2:19 pm
Nonstop2h 54m
Chicago O'Hare Intl
Mon 7/20
3:19 pm-6:59 pm
Nonstop2h 40m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/28
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 8/30
6:15 am-9:36 am
Nonstop2h 21m
$219
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.
BDL-MSP
ALB-ORD
ORH-ORD
BOS-ORD
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
BDL-MSP
ALB-ORD
ORH-ORD
BOS-ORD
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, April is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $68). 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 June 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 15% 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 June 21, 2026.
The most flights from USMA to USWI are scheduled on a Friday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Massachusetts to Wisconsin?
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 June 20, 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 afternoons 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 June 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
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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 June 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 2,558,603 searches. Data last updated June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$409 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$275 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$440 | FlexibilityNo cancel fee | On-time71% |