$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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Touko 31 — kesä 71
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 toukokuu 1, 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 toukokuu 1, 2026.
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ma 5/1810:17 am
BOS
- ORD
1 stop13h 56m
Multiple Airlines
la 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ke 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
ti 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 7/155:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
ti 7/2110:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 4/30![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ti 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
ti 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$164
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ti 7/78:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
ti 7/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/29![JetBlue logo]()
$165
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ti 6/167:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
ke 6/177:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/29![American Airlines logo]()
$166
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ke 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
la 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/28![Delta logo]()
$167
This SmartFares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
la 5/2311:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
su 5/248:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/28![JetBlue logo]()
$168
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ke 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
ke 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$169
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
to 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/30![JetBlue logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ke 5/275:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
ke 6/31:29 pm
ORD
- BOS
1 stop10h 55m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
la 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
pe 5/2910:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 4/27![Delta logo]()
$172
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 toukokuu 1, 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 toukokuu 1, 2026.
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 5/207:35 am
BOS
- ORD
Nonstop2h 52m
Delta
to 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 4/30![Delta logo]()
$182
This JetBlue deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 5/162:51 pm
BOS
- MKE
Nonstop2h 38m
JetBlue
ti 5/194:58 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/30![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ma 5/256:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
to 5/286:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 4/28![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ti 6/165:25 am
BOS
- ORD
2 stops8h 50m
Southwest
ke 6/172:40 pm
ORD
- BOS
2 stops7h 40m
Southwest
Deal found 4/30![Southwest logo]()
$197
This Sun Country Air deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
to 8/611:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
la 8/155:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 4/27![Sun Country Air logo]()
$374
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
su 6/77:30 am
BOS
- ORD
Nonstop2h 58m
Delta
pe 6/127:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/28![Delta logo]()
$201
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
su 5/315:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
ma 6/19:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/29![United Airlines logo]()
$209
This JetBlue deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
pe 5/226:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
to 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 4/30![JetBlue logo]()
$232
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ke 7/15:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
ma 7/69:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/27![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
pe 6/267:30 am
BOS
- ORD
Nonstop2h 58m
Delta
ma 6/297:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/26![Delta logo]()
$236
This JetBlue deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
su 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
ti 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/30![JetBlue logo]()
$257
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 5/236:40 pm
BOS
- MKE
1 stop4h 54m
United Airlines
ti 5/267:15 pm
MKE
- BOS
1 stop4h 59m
United Airlines
Deal found 4/30![United Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ke 6/109:15 am
BOS
- ORD
1 stop4h 49m
Delta
ke 6/107:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/28![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 6/135:50 am
BOS
- MKE
1 stop6h 40m
Southwest
to 6/185:50 pm
MKE
- BOS
1 stop4h 35m
Southwest
Deal found 4/30![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
pe 6/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
su 6/289:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/26![United Airlines logo]()
$241
This JetBlue deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
su 7/267:10 am
BOS
- MKE
Nonstop2h 35m
JetBlue
to 7/309:36 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 4/27![JetBlue logo]()
$293
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ke 7/16:00 pm
BOS
- MKE
1 stop6h 06m
Delta
su 7/56:00 am
MKE
- BOS
1 stop5h 23m
Delta
Deal found 4/26![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ma 5/185:40 am
BOS
- MKE
1 stop5h 10m
Southwest
pe 5/2212:40 pm
MKE
- BOS
2 stops10h 15m
Southwest
Deal found 4/26![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ma 5/48:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
to 5/76:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/30![United Airlines logo]()
$257
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ke 5/276:00 am
BOS
- MKE
1 stop5h 09m
United Airlines
ke 6/31:30 pm
MKE
- BOS
2 stops9h 29m
United Airlines
Deal found 4/29![United Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 6/2011:35 am
BOS
- MKE
Nonstop2h 41m
Delta
ti 6/236:49 pm
MKE
- BOS
1 stop4h 05m
Delta
Deal found 4/30![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
ke 8/126:20 pm
ALB
- MSP
1 stop4h 40m
Southwest
ma 8/177:55 am
MSP
- ALB
2 stops8h 30m
Southwest
Deal found 4/26![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 6/177:15 am
BOS
- GRB
1 stop5h 08m
Delta
la 6/206:00 pm
GRB
- BOS
1 stop4h 54m
Delta
Deal found 4/30![Delta logo]()
$309
This JetBlue deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
to 5/217:25 am
BDL
- ORD
1 stop8h 20m
JetBlue
pe 5/223:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 4/27![JetBlue logo]()
$380
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
to 5/287:20 pm
BDL
- MKE
1 stop3h 55m
Southwest
su 5/315:50 am
MKE
- BDL
1 stop3h 45m
Southwest
Deal found 4/26![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
pe 6/197:00 pm
BOS
- MKE
1 stop5h 34m
United Airlines
ti 6/231:30 pm
MKE
- BOS
2 stops9h 29m
United Airlines
Deal found 4/30![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
la 6/135:55 am
BOS
- GRB
1 stop6h 28m
Delta
ti 6/166:00 pm
GRB
- BOS
1 stop4h 54m
Delta
Deal found 4/27![Delta logo]()
$311
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.
ke 6/179:15 am
ALB
- MSP
2 stops8h 05m
Southwest
ti 6/235:25 am
MSP
- ALB
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$403
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
la 6/136:00 am
BOS
- GRB
1 stop5h 01m
United Airlines
ti 6/162:35 pm
GRB
- BOS
1 stop6h 21m
United Airlines
Deal found 4/28![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 6/65:51 am
BOS
- GRB
1 stop6h 22m
Delta
ma 6/86:00 pm
GRB
- BOS
1 stop4h 54m
Delta
Deal found 4/30![Delta logo]()
$334
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated toukokuu 1, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated toukokuu 1, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ma 5/1112:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
ti 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$180
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ma 5/116:00 am
BOS
- MKE
1 stop6h 14m
Multiple Airlines
ke 5/134:58 pm
MKE
- BOS
Nonstop2h 17m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$184
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ma 5/1112:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
ke 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ma 5/117:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
ke 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/27![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ma 5/118:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
ke 5/136:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/27![United Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
ti 5/125:45 am
BOS
- MKE
2 stops6h 46m
United Airlines
ke 5/135:15 am
MKE
- BOS
1 stop4h 46m
United Airlines
Deal found 4/27![United Airlines logo]()
$192
This Expedia deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 5/132:25 pm
BOS
- MKE
Nonstop2h 38m
Multiple Airlines
pe 5/1512:09 pm
MKE
- BOS
1 stop12h 15m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$189
This JetBlue deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
la 5/162:51 pm
BOS
- MKE
Nonstop2h 38m
JetBlue
ti 5/194:58 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/26![JetBlue logo]()
$187
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 5/186:00 am
BOS
- MKE
1 stop6h 14m
Frontier
ti 5/199:56 am
MKE
- BOS
1 stop22h 16m
Frontier
Deal found 5/1![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
la 5/236:00 am
BOS
- MKE
1 stop6h 34m
Multiple Airlines
ti 6/28:41 am
MKE
- BOS
Nonstop2h 19m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ma 5/256:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
pe 5/298:41 am
MKE
- BOS
Nonstop2h 19m
JetBlue
Deal found 4/29![JetBlue logo]()
$182
This Expedia deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ke 5/276:00 am
BOS
- MKE
1 stop6h 14m
Frontier
ke 6/312:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/29![Frontier logo]()
$180
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 toukokuu 1, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated toukokuu 1, 2026.
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 5/236:00 am
BOS
- MKE
1 stop6h 34m
Frontier
Deal found 4/30![Frontier logo]()
$70
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ti 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/29![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/30![JetBlue logo]()
$83
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
ke 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 4/28![JetBlue logo]()
$84
This Super.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
to 6/115:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 4/28![JetBlue logo]()
$87
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ma 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/30![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.
pe 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 4/27. Clicking the “Pick Dates” 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.
ke 5/136:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/27![Frontier logo]()
$89
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ma 6/227:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/29![Delta logo]()
$89
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
ke 5/276:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/30![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
la 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Deal found 4/30![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
ma 5/256:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 4/29![JetBlue logo]()
$93
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 toukokuu 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Expedia) |
One-way from | $70 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $277 |
Good round-trip deal | $154 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 toukokuu 1, 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
ke 5/20
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
to 5/28
10:25 am-1:49 pm
Nonstop2h 24m
$182
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
la 5/16
2:51 pm-4:29 pm
Nonstop2h 38m
Milwaukee-Mitchell
ti 5/19
4:58 pm-8:13 pm
Nonstop2h 15m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ma 5/25
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
to 5/28
6:00 am-11:16 am
1 stop4h 16m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ti 6/16
5:25 am-1:15 pm
2 stops8h 50m
Chicago O'Hare Intl
ke 6/17
2:40 pm-11:20 pm
2 stops7h 40m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
su 6/7
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
pe 6/12
7:25 pm-11:02 pm
Nonstop2h 37m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
su 5/31
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
ma 6/1
9:26 pm-12:59 am
Nonstop2h 33m
$209
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ke 7/1
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
ma 7/6
9:35 pm-1:08 am
Nonstop2h 33m
$219
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
pe 5/22
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
to 5/28
8:30 pm-11:59 pm
Nonstop2h 29m
$232
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
pe 6/26
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
ma 6/29
7:10 am-10:46 am
Nonstop2h 36m
$236
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
la 5/23
6:40 pm-10:34 pm
1 stop4h 54m
Milwaukee-Mitchell
ti 5/26
7:15 pm-1:14 am
1 stop4h 59m
$238
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-MKE
BOS-ORD
BDL-MSP
BOS-MSP
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-MKE
BOS-ORD
BDL-MSP
BOS-MSP
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 toukokuu 1, 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 34% 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 25, 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 toukokuu 1, 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.
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
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 toukokuu 1, 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 toukokuu 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$271 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$443 | FlexibilityNo cancel fee | On-time71% |