$83+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jun 5 — Jun 121
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 May 6, 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 May 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 5/1![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/215:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Wed 7/2210:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/2![JetBlue logo]()
$165
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/178:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 6/239:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$167
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/4![JetBlue logo]()
$169
This Super.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/158:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Mon 7/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/1![JetBlue logo]()
$170
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/307:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/177:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Sat 6/206:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 5/6![American Airlines logo]()
$173
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/2![Delta logo]()
$174
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/2![JetBlue logo]()
$175
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/298:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Fri 6/57:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/1![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/155:00 am
BOS
- ORD
Nonstop2h 58m
American Airlines
Mon 6/226:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 5/1![American Airlines logo]()
$178
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 May 6, 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 May 6, 2026.
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/27:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/36:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/2![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/2![Delta logo]()
$172
This JetBlue deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/5![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/155:25 am
BOS
- MKE
2 stops6h 30m
Southwest
Wed 7/155:05 pm
MKE
- BOS
1 stop4h 35m
Southwest
Deal found 5/2![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/27:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 6/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/2![United Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/2811:44 am
ALB
- ORD
1 stop5h 59m
American Airlines
Mon 6/15:10 am
ORD
- ALB
1 stop4h 43m
American Airlines
Deal found 5/1![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 5/307:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/4![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/247:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Wed 6/247:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 5/2![Delta logo]()
$202
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/298:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 6/309:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/5![United Airlines logo]()
$172
This Sun Country Air deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/911:04 am
BDL
- ORD
1 stop7h 15m
Sun Country Air
Sat 7/116:19 pm
ORD
- BDL
1 stop15h 38m
Sun Country Air
Deal found 5/2![Sun Country Air logo]()
$425
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/211:00 am
BOS
- MKE
1 stop7h 04m
Delta
Wed 6/105:56 pm
MKE
- BOS
1 stop4h 31m
Delta
Deal found 5/4![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/106:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 6/176:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/4![United Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/136:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 7/156:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/2![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/45:40 am
BOS
- MKE
1 stop4h 09m
Delta
Fri 6/125:56 pm
MKE
- BOS
1 stop4h 31m
Delta
Deal found 5/4![Delta logo]()
$252
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/35:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Wed 7/87:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/1![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/295:00 pm
BOS
- MKE
2 stops7h 10m
Southwest
Mon 8/37:00 am
MKE
- BOS
1 stop7h 15m
Southwest
Deal found 5/3![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/105:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 6/146:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/269:10 am
BOS
- MKE
Nonstop2h 40m
Delta
Mon 6/296:00 am
MKE
- BOS
1 stop6h 20m
Delta
Deal found 5/1![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 9/96:50 am
BDL
- MKE
1 stop7h 35m
Southwest
Wed 9/167:40 am
MKE
- BDL
1 stop5h 40m
Southwest
Deal found 5/2![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/25:30 am
BOS
- MKE
1 stop4h 21m
Delta
Mon 7/611:30 am
MKE
- BOS
Nonstop2h 29m
Delta
Deal found 5/2![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/285:00 am
ALB
- ORD
1 stop10h 20m
Southwest
Mon 6/12:40 pm
ORD
- ALB
2 stops7h 35m
Southwest
Deal found 5/1![Southwest logo]()
$350
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Fri 8/2810:57 am
ALB
- MSP
1 stop7h 06m
American Airlines
Mon 8/314:29 pm
MSP
- ALB
1 stop6h 02m
American Airlines
Deal found 5/1![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/1811:40 am
BOS
- MKE
Nonstop2h 35m
Delta
Wed 7/226:59 pm
MKE
- BOS
Nonstop2h 27m
Delta
Deal found 5/3![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/306:25 am
BDL
- MKE
1 stop8h 55m
Southwest
Tue 6/211:30 am
MKE
- BDL
2 stops8h 35m
Southwest
Deal found 5/6![Southwest logo]()
$370
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/205:38 am
ALB
- MSP
1 stop5h 26m
American Airlines
Fri 7/244:14 pm
MSP
- ALB
1 stop6h 09m
American Airlines
Deal found 5/1![American Airlines logo]()
$448
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/316:43 pm
BOS
- MKE
1 stop4h 46m
United Airlines
Tue 8/46:14 am
MKE
- BOS
1 stop6h 02m
United Airlines
Deal found 5/1![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/159:10 am
BOS
- MKE
Nonstop2h 44m
Delta
Wed 7/155:50 pm
MKE
- BOS
1 stop4h 41m
Delta
Deal found 5/2![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 8/126:20 pm
ALB
- MSP
1 stop4h 40m
Southwest
Mon 8/175:45 am
MSP
- ALB
1 stop4h 25m
Southwest
Deal found 5/4![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/175:03 pm
ALB
- ORD
1 stop4h 28m
Delta
Wed 6/243:22 pm
ORD
- ALB
1 stop7h 37m
Delta
Deal found 5/3![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/54:45 pm
BDL
- MKE
1 stop4h 45m
Southwest
Fri 8/78:00 am
MKE
- BDL
2 stops6h 05m
Southwest
Deal found 5/5![Southwest logo]()
$396
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated May 6, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/2![JetBlue logo]()
$175
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/2![Delta logo]()
$174
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 5/298:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$170
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/266:00 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Thu 5/281:50 pm
ORD
- BOS
1 stop10h 34m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$179
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/298:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/319:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/307:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$172
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/16:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Fri 6/512:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 5/4![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/210:35 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sat 6/63:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 5/5![United Airlines logo]()
$167
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/4![JetBlue logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Tue 6/1610:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 5/1![JetBlue logo]()
$162
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/177:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Sat 6/206:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 5/6![American Airlines logo]()
$173
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 May 6, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 8/58:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/4![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/2![Delta logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/2712:01 pm
BOS
- ORD
1 stop8h 40m
Frontier
Deal found 5/6![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/5![JetBlue logo]()
$88
This Sun Country Air deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/291:12 pm
BDL
- MSP
Nonstop2h 58m
Sun Country Air
Deal found 5/1![Sun Country Air logo]()
$89
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/206:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 5/3![Frontier logo]()
$89
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/410:35 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/1![United Airlines logo]()
$89
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Sat 6/66:00 am
BOS
- MKE
1 stop6h 34m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/812:01 pm
BOS
- ORD
1 stop8h 28m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Thu 6/46:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 5/5![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/2311:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 5/5![JetBlue logo]()
$92
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $83 (Super.com) |
Popular in | November |
Cheapest in | September |
Average price | $277 |
Good round-trip deal | $185 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 May 6, 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
Tue 6/2
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 6/3
6:05 am-9:29 am
Nonstop2h 24m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 6/9
9:41 pm-1:14 am
Nonstop2h 33m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/23
5:30 pm-7:33 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 5/24
7:00 am-10:35 am
Nonstop2h 35m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 5/30
7:45 pm-11:21 pm
Nonstop2h 36m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
8:20 pm-10:20 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 6/30
9:41 pm-1:14 am
Nonstop2h 33m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/10
6:40 pm-8:40 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 6/17
6:00 am-11:16 am
1 stop4h 16m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 6/8
8:30 pm-11:59 pm
Nonstop2h 29m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/13
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 7/15
6:00 am-11:16 am
1 stop4h 16m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/3
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Wed 7/8
7:45 pm-11:21 pm
Nonstop2h 36m
$196
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/10
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sun 6/14
6:05 am-9:29 am
Nonstop2h 24m
$196
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
BDL-MSP
BOS-MKE
BDL-MSN
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
BDL-MSP
BOS-MKE
BDL-MSN
How far ahead should I book a flight from Massachusetts to Wisconsin?
Booking 89 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 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 May 6, 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 19% 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 May 2, 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. Wednesday 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 May 6, 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
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
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
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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 May 6, 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$456 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$442 | FlexibilityNo cancel fee | On-time71% |