$64+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Apr 6 — Apr 131
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 March 7, 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 March 7, 2026.
This CheapOair deal was found by Cheapflights users on 3/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Wed 4/157:15 pm
ORD
- BOS
1 stop14h 00m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:55 pm
BOS
- ORD
1 stop10h 44m
Frontier
Mon 5/114:28 pm
ORD
- BOS
1 stop7h 23m
Frontier
Deal found 3/3![Frontier logo]()
$130
This Expedia deal was found by Cheapflights users on 3/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Wed 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/3![JetBlue logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Wed 4/229:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/3![JetBlue logo]()
$132
This Super.com deal was found by Cheapflights users on 3/3. 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 4/86:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/3![JetBlue logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:20 am
BOS
- ORD
1 stop18h 19m
Frontier
Wed 4/1511:07 am
ORD
- BOS
1 stop13h 24m
Frontier
Deal found 3/3![Frontier logo]()
$134
This Delta deal was found by Cheapflights users on 3/4. 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 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 3/4![Delta logo]()
$136
This Priceline deal was found by Cheapflights users on 3/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:36 pm
BOS
- ORD
1 stop6h 57m
Multiple Airlines
Sun 4/58:55 am
ORD
- BOS
Nonstop2h 32m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Mon 5/114:28 pm
ORD
- BOS
1 stop7h 23m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:44 pm
ORH
- ORD
1 stop5h 20m
American Airlines
Sat 3/217:58 pm
ORD
- ORH
1 stop16h 21m
American Airlines
Deal found 3/2![American Airlines logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 3/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:00 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Mon 6/157:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 3/4![Sun Country Air logo]()
$168
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Sat 5/26:05 am
ORD
- ORH
2 stops7h 09m
American Airlines
Deal found 3/2![American Airlines logo]()
$175
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 March 7, 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 March 7, 2026.
This United Airlines deal was found by Cheapflights users on 3/4. 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 7/16:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 7/43:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 3/4![United Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Tue 5/197:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 3/6![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 3/4. 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 5/65:35 am
BOS
- ORD
1 stop10h 25m
Southwest
Fri 5/82:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 3/4![Southwest logo]()
$157
This Priceline deal was found by Cheapflights users on 3/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 6/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/6![JetBlue logo]()
$162
This American Airlines deal was found by Cheapflights users on 3/6. 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.
Sat 3/211:44 pm
ORH
- ORD
2 stops18h 41m
American Airlines
Wed 3/258:45 pm
ORD
- ORH
2 stops15h 34m
American Airlines
Deal found 3/6![American Airlines logo]()
$216
This Sun Country Air deal was found by Cheapflights users on 3/6. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1811:38 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Mon 7/276:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 3/6![Sun Country Air logo]()
$264
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Mon 6/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Fri 6/59:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/4![United Airlines logo]()
$137
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 3/6![United Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 3/4. 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.
Mon 5/45:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Thu 5/77:05 am
ORD
- ORH
1 stop7h 28m
Delta
Deal found 3/4![Delta logo]()
$192
This JetBlue deal was found by Cheapflights users on 3/5. 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.
Mon 5/46:52 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Wed 5/68:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Deal found 3/5![JetBlue logo]()
$207
This Southwest deal was found by Cheapflights users on 3/2. 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.
Thu 5/75:40 am
BOS
- MKE
1 stop5h 10m
Southwest
Mon 5/113:30 pm
MKE
- BOS
1 stop7h 25m
Southwest
Deal found 3/2![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Thu 7/27:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/27:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 3/4![United Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
BOS
- MKE
1 stop5h 18m
Delta
Mon 6/86:25 pm
MKE
- BOS
1 stop4h 07m
Delta
Deal found 3/6![Delta logo]()
$207
This JetBlue deal was found by Cheapflights users on 3/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:15 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Tue 6/239:41 am
MKE
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/2![JetBlue logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Sat 4/184:20 pm
ORD
- BOS
1 stop6h 39m
United Airlines
Deal found 3/3![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 3/4. 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 4/15:30 am
BOS
- MKE
1 stop5h 15m
Southwest
Wed 4/85:50 am
MKE
- BOS
2 stops9h 05m
Southwest
Deal found 3/4![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/2. 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 4/84:33 pm
ORH
- ORD
1 stop6h 39m
Delta
Thu 4/99:35 am
ORD
- ORH
1 stop5h 15m
Delta
Deal found 3/2![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 3/4. 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.
Sun 5/105:40 am
BOS
- MKE
1 stop4h 09m
Delta
Sun 5/246:00 am
MKE
- BOS
1 stop5h 20m
Delta
Deal found 3/4![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 3/1. 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 3/191:44 pm
ORH
- ORD
2 stops18h 41m
American Airlines
Sat 3/218:55 pm
ORD
- ORH
1 stop15h 24m
American Airlines
Deal found 3/1![American Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/216:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/246:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 3/6![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:40 am
BOS
- MKE
1 stop4h 09m
Delta
Mon 5/256:00 am
MKE
- BOS
1 stop7h 15m
Delta
Deal found 3/6![Delta logo]()
$217
This Sun Country Air deal was found by Cheapflights users on 3/1. 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.
Thu 7/911:40 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Mon 7/136:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 3/1![Sun Country Air logo]()
$319
This United Airlines deal was found by Cheapflights users on 3/1. 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 6/258:00 am
BOS
- ORD
1 stop5h 06m
United Airlines
Fri 6/269:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/1![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 3/5. 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.
Sat 5/2312:50 pm
BOS
- MKE
2 stops8h 20m
Southwest
Tue 6/22:45 pm
MKE
- BOS
1 stop6h 55m
Southwest
Deal found 3/5![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Tue 6/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Fri 7/39:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/4![United Airlines logo]()
$221
This JetBlue deal was found by Cheapflights users on 3/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/102:09 pm
BOS
- MKE
Nonstop2h 30m
JetBlue
Sun 5/248:26 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 3/4![JetBlue logo]()
$342
This Delta deal was found by Cheapflights users on 3/4. 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.
Fri 6/193:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Mon 6/227:00 am
ORD
- ORH
1 stop6h 39m
Delta
Deal found 3/4![Delta logo]()
$273
This Sun Country Air deal was found by Cheapflights users on 3/4. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2511:52 am
BDL
- ORD
1 stop8h 52m
Sun Country Air
Sun 6/288:24 pm
ORD
- BDL
1 stop13h 23m
Sun Country Air
Deal found 3/4![Sun Country Air logo]()
$447
This Delta deal was found by Cheapflights users on 3/1. 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.
Wed 5/134:15 pm
ORH
- ORD
1 stop7h 21m
Delta
Sat 5/162:40 pm
ORD
- ORH
1 stop23h 53m
Delta
Deal found 3/1![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 3/2. 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.
Fri 6/51:10 pm
BOS
- MSP
1 stop4h 50m
Southwest
Tue 6/95:25 am
MSP
- BOS
2 stops7h 25m
Southwest
Deal found 3/2![Southwest logo]()
$384
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 7, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:44 pm
ORH
- ORD
1 stop5h 20m
American Airlines
Sat 3/217:58 pm
ORD
- ORH
1 stop16h 21m
American Airlines
Deal found 3/2![American Airlines logo]()
$160
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Sun 3/226:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 3/244:20 pm
ORD
- BOS
Nonstop2h 22m
United Airlines
Deal found 3/2![United Airlines logo]()
$141
This Priceline deal was found by Cheapflights users on 3/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:36 pm
BOS
- ORD
1 stop6h 57m
Multiple Airlines
Sun 4/58:55 am
ORD
- BOS
Nonstop2h 32m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$139
This Expedia deal was found by Cheapflights users on 3/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Wed 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/3![JetBlue logo]()
$131
This Delta deal was found by Cheapflights users on 3/4. 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 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 3/4![Delta logo]()
$136
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Sat 4/118:05 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/2![American Airlines logo]()
$142
This CheapOair deal was found by Cheapflights users on 3/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Wed 4/157:15 pm
ORD
- BOS
1 stop14h 00m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$129
This Super.com deal was found by Cheapflights users on 3/3. 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 4/86:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/3![JetBlue logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:20 am
BOS
- ORD
1 stop18h 19m
Frontier
Wed 4/1511:07 am
ORD
- BOS
1 stop13h 24m
Frontier
Deal found 3/3![Frontier logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Wed 4/229:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/3![JetBlue logo]()
$132
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Sat 5/26:05 am
ORD
- ORH
2 stops7h 09m
American Airlines
Deal found 3/2![American Airlines logo]()
$175
This JetBlue deal was found by Cheapflights users on 3/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:04 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Tue 5/54:34 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/3![JetBlue logo]()
$197
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 March 7, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 7, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/3![JetBlue logo]()
$64
This Southwest deal was found by Cheapflights users on 3/2. 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.
Sat 5/95:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 3/2![Southwest logo]()
$65
This Trip.com deal was found by Cheapflights users on 3/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 3/3![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:35 pm
BOS
- ORD
1 stop23h 09m
Frontier
Deal found 3/3![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/3![Frontier logo]()
$67
This Super.com deal was found by Cheapflights users on 3/4. 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.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/4![JetBlue logo]()
$68
This Southwest deal was found by Cheapflights users on 3/2. 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.
Tue 4/78:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Deal found 3/2![Southwest logo]()
$69
This Trip.com deal was found by Cheapflights users on 3/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 3/2![Frontier logo]()
$70
This Cheapflightsfares deal was found by Cheapflights users on 3/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:45 am
BOS
- ORD
1 stop11h 18m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$70
This Priceline deal was found by Cheapflights users on 3/4. 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 4/145:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$71
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 5/86:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/2![United Airlines logo]()
$72
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:15 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 3/3![United Airlines logo]()
$73
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 March 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $128 (Southwest) |
One-way from | $64 (Cheapflightsfares) |
Popular in | November |
Cheapest in | September |
Average price | $369 |
Good round-trip deal | $287 or less |
Good one-way deal | $158 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 March 7, 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
Wed 7/1
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sat 7/4
3:55 pm-7:30 pm
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/13
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 5/19
7:00 am-10:35 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/1
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Fri 6/5
9:26 pm-12:59 am
Nonstop2h 33m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/31
7:15 am-9:14 am
Nonstop2h 59m
Chicago O'Hare Intl
Sun 4/5
6:00 am-9:25 am
Nonstop2h 25m
$147
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/6
5:35 am-3:00 pm
1 stop10h 25m
Chicago O'Hare Intl
Fri 5/8
2:40 pm-11:15 pm
1 stop7h 35m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 6/21
8:00 am-9:56 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 6/24
8:20 pm-11:51 pm
Nonstop2h 31m
$162
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/2
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/2
7:40 pm-11:16 pm
Nonstop2h 36m
$181
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/16
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Sat 4/18
4:20 pm-11:59 pm
1 stop6h 39m
$185
WorcesterChicago
ORH - ORD
ORHORD
Worcester
Mon 5/4
5:24 pm-10:15 pm
1 stop5h 51m
Chicago O'Hare Intl
Thu 5/7
7:05 am-3:33 pm
1 stop7h 28m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/4
6:52 am-8:51 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 5/6
8:31 am-2:16 pm
1 stop4h 45m
$207
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
ORH-ORD
BOS-MSP
BOS-MKE
BDL-ORD
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
ORH-ORD
BOS-MSP
BOS-MKE
What is the cheapest month to book a flight from Massachusetts to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in December is currently the most expensive (average of $254). 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 March 7, 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 50% versus a flight in the evening.
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 February 21, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 7, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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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 March 7, 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 March 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$277 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$206 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$218 | Average$442 | FlexibilityNo cancel fee | On-time69% |