$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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Apr 22 — Apr 291
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 23, 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 23, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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
Wed 4/156:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 6/238:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/20![JetBlue logo]()
$152
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/116:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/148:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Tue 4/142:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 3/22![Southwest logo]()
$155
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/16:39 pm
BOS
- ORD
Nonstop3h 01m
United Airlines
Sun 5/39:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 3/22![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/20![American Airlines logo]()
$158
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Tue 4/146:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Sat 4/184:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:31 pm
BOS
- ORD
1 stop11h 08m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/20![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Mon 6/85:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Thu 6/188:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/23![JetBlue logo]()
$162
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Mon 4/206:00 am
ORD
- BOS
Nonstop2h 13m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$164
This Priceline deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Wed 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$166
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 23, 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 23, 2026.
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 6/39:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/18![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Mon 5/112:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Deal found 3/19![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Mon 4/206:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/18![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BOS
- ATW
2 stops7h 56m
American Airlines
Wed 4/297:01 am
ATW
- BOS
1 stop7h 33m
American Airlines
Deal found 3/18![American Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/98:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Sun 4/127:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/22![United Airlines logo]()
$167
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:20 am
BOS
- ORD
2 stops10h 45m
Southwest
Sat 5/301:55 pm
ORD
- BOS
2 stops8h 45m
Southwest
Deal found 3/18![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 6/137:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Tue 6/169:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/22![United Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:53 pm
ALB
- ORD
1 stop17h 44m
Multiple Airlines
Sun 5/317:52 pm
ORD
- ALB
2 stops22h 11m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:20 am
BOS
- ORD
2 stops11h 10m
Southwest
Sat 5/91:55 pm
ORD
- BOS
1 stop7h 10m
Southwest
Deal found 3/18![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:05 am
BOS
- ORD
1 stop6h 00m
United Airlines
Sat 4/114:20 pm
ORD
- BOS
1 stop6h 39m
United Airlines
Deal found 3/19![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:30 am
BOS
- MKE
1 stop4h 11m
Delta
Mon 6/157:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Deal found 3/18![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:30 am
BOS
- ORD
2 stops8h 20m
Southwest
Wed 4/292:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 3/19![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/19:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 4/47:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/22![United Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
BOS
- ATW
2 stops8h 00m
American Airlines
Wed 4/1510:57 am
ATW
- BOS
1 stop4h 48m
American Airlines
Deal found 3/19![American Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 9/55:30 am
BOS
- MKE
1 stop4h 11m
Delta
Mon 9/76:25 pm
MKE
- BOS
1 stop4h 07m
Delta
Deal found 3/21![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/167:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 4/206:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 3/21![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:16 pm
BOS
- ATW
1 stop5h 38m
Delta
Wed 5/276:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 3/20![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/274:30 pm
BOS
- ATW
1 stop7h 03m
Delta
Sat 6/66:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 3/21![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/226:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/246:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 3/21![United Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/29:00 am
BOS
- MSP
1 stop6h 10m
Southwest
Tue 5/52:15 pm
MSP
- BOS
1 stop7h 15m
Southwest
Deal found 3/22![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:00 pm
BOS
- ATW
1 stop7h 37m
Delta
Wed 4/296:19 pm
ATW
- BOS
1 stop4h 33m
Delta
Deal found 3/18![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/285:51 am
BOS
- ATW
1 stop7h 00m
Delta
Sat 6/66:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 3/21![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/910:40 am
BOS
- MKE
2 stops9h 30m
Southwest
Sat 4/115:00 am
MKE
- BOS
2 stops7h 35m
Southwest
Deal found 3/21![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/76:00 am
BOS
- MKE
1 stop5h 10m
United Airlines
Thu 4/95:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 3/22![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/273:00 pm
BOS
- ATW
1 stop8h 33m
Delta
Fri 6/56:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 3/21![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/297:00 pm
BOS
- MKE
1 stop5h 34m
United Airlines
Sun 5/317:00 pm
MKE
- BOS
1 stop4h 59m
United Airlines
Deal found 3/22![United Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/96:00 am
ALB
- MSP
2 stops9h 10m
Southwest
Tue 5/123:15 pm
MSP
- ALB
1 stop4h 35m
Southwest
Deal found 3/21![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/285:51 am
BOS
- ATW
1 stop7h 00m
Delta
Fri 6/56:18 pm
ATW
- BOS
1 stop4h 11m
Delta
Deal found 3/21![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:15 am
BOS
- ATW
1 stop6h 50m
United Airlines
Fri 5/295:30 pm
ATW
- BOS
1 stop4h 45m
United Airlines
Deal found 3/19![United Airlines logo]()
$292
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:25 pm
ALB
- MSP
1 stop4h 35m
Southwest
Tue 5/195:20 am
MSP
- ALB
2 stops7h 45m
Southwest
Deal found 3/18![Southwest logo]()
$360
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated March 23, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Wed 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$170
This Priceline deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Wed 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$166
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Sun 4/127:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/20![United Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/19![American Airlines logo]()
$168
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:45 am
BOS
- MKE
2 stops6h 47m
United Airlines
Fri 4/107:41 pm
MKE
- BOS
1 stop4h 18m
United Airlines
Deal found 3/19![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/20![American Airlines logo]()
$158
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Tue 4/146:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Tue 4/146:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Sat 4/184:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/148:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Tue 4/142:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 3/22![Southwest logo]()
$155
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Wed 4/229:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/20![United Airlines logo]()
$157
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Mon 4/206:00 am
ORD
- BOS
Nonstop2h 13m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$164
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 23, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 23, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Thu 4/163:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 3/21![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Flysmarter deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/18![JetBlue logo]()
$74
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Deal found 3/20![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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 3/20![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:50 pm
BDL
- ORD
1 stop29h 01m
Frontier
Deal found 3/18![Frontier logo]()
$78
This Super.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 3/18![JetBlue logo]()
$78
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:20 pm
BOS
- MKE
Nonstop2h 48m
Delta
Deal found 3/20![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 3/20![Delta logo]()
$79
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Fri 4/248:42 pm
BDL
- ORD
1 stop19h 41m
Frontier
Deal found 3/21![Frontier logo]()
$82
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/297:35 am
BOS
- ORD
2 stops9h 30m
Southwest
Deal found 3/22![Southwest logo]()
$83
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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $70 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $442 |
Good round-trip deal | $217 or less |
Good one-way deal | $163 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 23, 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 5/27
8:05 pm-10:05 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 6/3
9:26 pm-12:59 am
Nonstop2h 33m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/9
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Sun 4/12
7:30 am-11:01 am
Nonstop2h 31m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/13
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Tue 6/16
9:26 pm-12:59 am
Nonstop2h 33m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/4
8:25 am-12:50 pm
1 stop5h 25m
Chicago O'Hare Intl
Mon 5/11
2:40 pm-11:55 pm
2 stops8h 15m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/27
6:20 am-4:05 pm
2 stops10h 45m
Chicago O'Hare Intl
Sat 5/30
1:55 pm-11:40 pm
2 stops8h 45m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 4/11
7:05 am-12:05 pm
1 stop6h 00m
Chicago O'Hare Intl
Sat 4/11
4:20 pm-11:59 pm
1 stop6h 39m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/1
9:20 am-11:20 am
Nonstop3h 00m
Chicago O'Hare Intl
Sat 4/4
7:30 am-11:01 am
Nonstop2h 31m
$205
Quickest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/16
7:00 am-9:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 4/20
6:00 am-9:25 am
Nonstop2h 25m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/7
7:20 am-5:30 pm
2 stops11h 10m
Chicago O'Hare Intl
Sat 5/9
1:55 pm-10:05 pm
1 stop7h 10m
$212
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/16
7:10 am-9:15 am
Nonstop3h 05m
Chicago O'Hare Intl
Mon 4/20
6:50 am-10:11 am
Nonstop2h 21m
$217
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Massachusetts with our price prediction graph.
BOS-ORD
BOS-MKE
BOS-ATW
ALB-ORD
BOS-MSP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Wisconsin
USMA-USWI
BOS-ORD
BOS-MKE
BOS-ATW
ALB-ORD
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 23, 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 45% 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 March 23, 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.
Weekly flight availability from Massachusetts to Wisconsin
Explore weekly flight availability from Massachusetts to Wisconsin. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 23, 2026.
The most flights from USMA to USWI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
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 23, 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.
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 23, 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$274 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$135 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$206 | Average$422 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$218 | Average$440 | FlexibilityNo cancel fee | On-time69% |