$59+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 4 — May 111
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 April 4, 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 April 4, 2026.
This SmartFares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/31![JetBlue logo]()
$138
This Expedia deal was found by Cheapflights users on 3/30. 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.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/30![Frontier logo]()
$140
This SmartFares deal was found by Cheapflights users on 3/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/30![JetBlue logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/286:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/2812:52 pm
BOS
- ORD
1 stop22h 31m
Multiple Airlines
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$149
This SmartFares deal was found by Cheapflights users on 4/3. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/3![JetBlue logo]()
$150
This SmartFares deal was found by Cheapflights users on 4/3. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/3![JetBlue logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/297:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Wed 5/69:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/2812:52 pm
BOS
- ORD
1 stop22h 31m
Multiple Airlines
Mon 5/44:28 pm
ORD
- BOS
1 stop15h 06m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$155
This CheapOair deal was found by Cheapflights users on 4/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Sun 5/109:56 am
MKE
- BOS
1 stop22h 36m
Frontier
Deal found 4/4![Frontier logo]()
$192
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 April 4, 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 April 4, 2026.
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
BOS
- ORD
Nonstop3h 04m
Delta
Mon 5/117:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/3![Delta logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Wed 4/295:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Fri 5/11:55 pm
ORD
- BOS
Nonstop2h 27m
United Airlines
Deal found 4/2![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 4/2. 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 5/25:15 am
BOS
- ORD
1 stop10h 05m
Southwest
Sat 5/912:15 pm
ORD
- BOS
2 stops10h 25m
Southwest
Deal found 4/2![Southwest logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 6/137:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Sat 6/206:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/3![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 4/2. 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.
Fri 8/288:10 pm
BOS
- ORD
Nonstop2h 56m
Delta
Sun 8/307:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 4/2![Delta logo]()
$205
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:20 am
BOS
- ORD
2 stops11h 10m
Southwest
Fri 5/82:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Deal found 4/3![Southwest logo]()
$207
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:21 pm
ALB
- ORD
Nonstop2h 57m
American Airlines
Thu 4/169:55 am
ORD
- ALB
1 stop5h 37m
American Airlines
Deal found 4/1![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Wed 5/205:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Sun 5/247:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 4/3![United Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 4/1. 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.
Tue 5/265:40 am
BOS
- MKE
1 stop4h 09m
Delta
Mon 6/16:55 pm
MKE
- BOS
Nonstop2h 21m
Delta
Deal found 4/1![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:15 pm
BOS
- MKE
1 stop5h 55m
Southwest
Sat 5/302:55 pm
MKE
- BOS
2 stops7h 45m
Southwest
Deal found 4/3![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/1. 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 9/35:45 am
BOS
- ORD
1 stop4h 48m
United Airlines
Sun 9/69:30 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/1![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 4/306:00 am
BOS
- ORD
1 stop6h 05m
Delta
Sun 5/36:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/30![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:30 am
BOS
- ORD
1 stop6h 15m
Delta
Sat 7/410:29 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 3/31![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 4/4. 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.
Sat 5/29:25 am
BOS
- ORD
1 stop4h 24m
Delta
Mon 5/46:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 4/4![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:00 pm
BOS
- MKE
1 stop5h 52m
Delta
Mon 9/76:25 pm
MKE
- BOS
1 stop4h 07m
Delta
Deal found 4/3![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:50 am
BOS
- MKE
1 stop7h 05m
Southwest
Mon 9/2112:30 pm
MKE
- BOS
1 stop6h 10m
Southwest
Deal found 4/1![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/2911:17 am
BOS
- MKE
2 stops8h 30m
United Airlines
Sun 5/35:10 am
MKE
- BOS
1 stop4h 51m
United Airlines
Deal found 3/30![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/2. 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 6/92:35 pm
BDL
- MKE
2 stops8h 25m
Southwest
Wed 6/106:45 am
MKE
- BDL
1 stop6h 15m
Southwest
Deal found 4/2![Southwest logo]()
$340
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:38 am
ALB
- MSP
1 stop5h 26m
American Airlines
Fri 7/245:46 pm
MSP
- ALB
1 stop4h 57m
American Airlines
Deal found 3/30![American Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/285:10 pm
BDL
- MSN
1 stop5h 11m
United Airlines
Tue 5/56:30 am
MSN
- BDL
1 stop6h 48m
United Airlines
Deal found 3/30![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:15 pm
ALB
- MSP
2 stops8h 40m
Southwest
Sat 5/97:25 am
MSP
- ALB
2 stops8h 00m
Southwest
Deal found 4/3![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 4/1. 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.
Thu 9/179:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Mon 9/216:25 pm
MKE
- BOS
1 stop4h 07m
Delta
Deal found 4/1![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Fri 5/226:10 am
ALB
- ORD
Nonstop2h 37m
United Airlines
Mon 5/256:25 pm
ORD
- ALB
Nonstop2h 18m
United Airlines
Deal found 4/3![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 4/2. 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 5/212:35 pm
ALB
- MSP
1 stop5h 40m
Southwest
Mon 5/42:25 pm
MSP
- ALB
2 stops7h 50m
Southwest
Deal found 4/2![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
BOS
- MKE
1 stop5h 54m
Delta
Sun 5/177:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/3![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 8/56:09 am
BDL
- MSN
1 stop4h 50m
United Airlines
Wed 8/125:00 am
MSN
- BDL
2 stops7h 59m
United Airlines
Deal found 3/30![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/308:45 am
BDL
- MKE
1 stop4h 25m
Southwest
Mon 5/43:30 pm
MKE
- BDL
1 stop6h 40m
Southwest
Deal found 3/30![Southwest logo]()
$375
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Sun 6/216:00 am
BOS
- MKE
1 stop6h 14m
United Airlines
Sun 6/217:00 pm
MKE
- BOS
1 stop4h 59m
United Airlines
Deal found 4/1![United Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 4/286:00 am
BDL
- MSN
1 stop5h 09m
Delta
Tue 5/55:04 pm
MSN
- BDL
1 stop5h 55m
Delta
Deal found 3/30![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 5/811:40 am
ALB
- MSP
1 stop5h 00m
Southwest
Tue 5/127:50 am
MSP
- ALB
2 stops9h 10m
Southwest
Deal found 4/1![Southwest logo]()
$376
Last-minute flights from Massachusetts to WisconsinDiscover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Wisconsin. Data last updated April 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$149
This Expedia deal was found by Cheapflights users on 3/30. 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.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/30![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/286:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/2812:52 pm
BOS
- ORD
1 stop22h 31m
Multiple Airlines
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Tue 4/287:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 3/30![JetBlue logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/2812:52 pm
BOS
- ORD
1 stop22h 31m
Multiple Airlines
Mon 5/44:28 pm
ORD
- BOS
1 stop15h 06m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$155
This SmartFares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/31![JetBlue logo]()
$138
This SmartFares deal was found by Cheapflights users on 4/3. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/3![JetBlue logo]()
$150
This CheapOair deal was found by Cheapflights users on 4/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Sun 5/109:56 am
MKE
- BOS
1 stop22h 36m
Frontier
Deal found 4/4![Frontier logo]()
$192
This SmartFares deal was found by Cheapflights users on 4/3. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/3![JetBlue logo]()
$151
This SmartFares deal was found by Cheapflights users on 3/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/30![JetBlue logo]()
$143
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 April 4, 2026.
Search for one-way flight options from Massachusetts to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 4, 2026.
This KAYAK deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:04 pm
BOS
- MKE
Nonstop2h 36m
JetBlue
Deal found 3/31![JetBlue logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$68
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/149:10 am
BOS
- MKE
Nonstop2h 43m
Delta
Deal found 3/31![Delta logo]()
$69
This Expedia deal was found by Cheapflights users on 4/3. 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.
Mon 5/256:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/3![Frontier logo]()
$70
This SmartFares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 3/31![JetBlue logo]()
$72
This Delta deal was found by Cheapflights users on 3/30. 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.
Fri 5/15:20 pm
BOS
- MKE
Nonstop2h 56m
Delta
Deal found 3/30![Delta logo]()
$74
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/276:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/31![JetBlue logo]()
$78
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/291:00 pm
BOS
- MKE
1 stop5h 16m
Delta
Deal found 3/31![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 4/224:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/30![Delta logo]()
$79
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/153:59 pm
BOS
- MKE
1 stop5h 07m
American Airlines
Deal found 3/31![American Airlines logo]()
$80
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 April 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $138 (SmartFares) |
One-way from | $59 (KAYAK) |
Popular in | November |
Cheapest in | September |
Average price | $439 |
Good round-trip deal | $178 or less |
Good one-way deal | $223 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 April 4, 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
Sat 5/9
7:35 am-9:39 am
Nonstop3h 04m
Chicago O'Hare Intl
Mon 5/11
7:00 am-10:35 am
Nonstop2h 35m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/29
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Fri 5/1
1:55 pm-5:22 pm
Nonstop2h 27m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/13
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Sat 6/20
6:20 pm-9:56 pm
Nonstop2h 36m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
5:15 am-2:20 pm
1 stop10h 05m
Chicago O'Hare Intl
Sat 5/9
12:15 pm-11:40 pm
2 stops10h 25m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/28
8:10 pm-10:06 pm
Nonstop2h 56m
Chicago O'Hare Intl
Sun 8/30
7:00 am-10:28 am
Nonstop2h 28m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/4
7:20 am-5:30 pm
2 stops11h 10m
Chicago O'Hare Intl
Fri 5/8
2:40 pm-11:55 pm
2 stops8h 15m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/20
5:45 am-9:37 am
1 stop4h 52m
Chicago O'Hare Intl
Sun 5/24
7:33 am-11:05 am
Nonstop2h 32m
$212
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Tue 5/26
5:40 am-8:49 am
1 stop4h 09m
Milwaukee-Mitchell
Mon 6/1
6:55 pm-10:16 pm
Nonstop2h 21m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/3
5:45 am-9:33 am
1 stop4h 48m
Chicago O'Hare Intl
Sun 9/6
9:30 pm-1:05 am
Nonstop2h 35m
$235
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/30
6:00 am-11:05 am
1 stop6h 05m
Chicago O'Hare Intl
Sun 5/3
6:50 am-10:11 am
Nonstop2h 21m
$236
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
BDL-MKE
BDL-MSP
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
BOS-MKE
BDL-MKE
BDL-MSP
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 $97). 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 April 4, 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 21% versus a flight in the afternoon.
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 28, 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 April 4, 2026.
The most flights from USMA to USWI are scheduled on a Tuesday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
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 April 4, 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.
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
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 April 4, 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 April 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$271 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$135 | Average$404 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$270 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$206 | Average$428 | FlexibilityNo cancel fee | On-time71% |