$64+ Cheap flights from Boston (BOS) 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Mar 31 — Apr 71
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Wisconsin with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Wisconsin
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to WisconsinExplore the most affordable flight options available from Boston to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 1, 2026.
Explore the most affordable flight options available from Boston to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 1, 2026.
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:00 am
BOS
- ORD
1 stop7h 30m
Southwest
Mon 5/112:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 2/27![Southwest logo]()
$128
This Priceline deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Thu 4/164:28 pm
ORD
- BOS
1 stop8h 03m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Sat 4/188:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 2/25![American Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:00 am
BOS
- ORD
Nonstop2h 52m
Delta
Wed 9/910:10 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 2/27![Delta logo]()
$131
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/208:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Sun 5/246:00 am
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 2/25![American Airlines logo]()
$132
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/16:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/47:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 2/25![United Airlines logo]()
$133
This Expedia deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Fri 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:09 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Wed 3/257:18 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 2/27![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/27![Delta logo]()
$137
This Priceline deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Wed 9/27:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Deal found 2/28![Delta logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
BOS
- MKE
Nonstop2h 36m
JetBlue
Tue 6/28:26 am
MKE
- BOS
Nonstop2h 18m
JetBlue
Deal found 2/27![JetBlue logo]()
$192
Best flights from Boston to WisconsinDiscover carefully curated flight deals from Boston to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 1, 2026.
Discover carefully curated flight deals from Boston to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 1, 2026.
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 4/137:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 2/27![United Airlines logo]()
$142
This JetBlue deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Thu 4/168:31 am
ORD
- BOS
1 stop4h 47m
JetBlue
Deal found 2/27![JetBlue logo]()
$171
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/118:20 pm
BOS
- ORD
Nonstop2h 56m
Delta
Fri 3/137:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/25![Delta logo]()
$181
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop5h 20m
Southwest
Deal found 2/28![Southwest logo]()
$217
This Sun Country Air deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Tue 7/1411:40 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Sat 7/186:55 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 2/25![Sun Country Air logo]()
$254
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:59 pm
BOS
- LSE
1 stop8h 55m
American Airlines
Sun 5/246:00 am
LSE
- BOS
1 stop10h 33m
American Airlines
Deal found 2/28![American Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:35 pm
BOS
- ORD
Nonstop3h 06m
United Airlines
Fri 3/62:35 pm
ORD
- BOS
1 stop4h 40m
United Airlines
Deal found 2/27![United Airlines logo]()
$171
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/106:00 am
BOS
- ORD
1 stop5h 51m
United Airlines
Tue 3/106:05 pm
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 2/25![United Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/184:50 pm
BOS
- MKE
Nonstop2h 50m
Delta
Mon 3/237:25 pm
MKE
- BOS
Nonstop2h 16m
Delta
Deal found 2/25![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/177:55 am
BOS
- ORD
Nonstop3h 05m
Delta
Tue 4/217:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 2/25![Delta logo]()
$207
This JetBlue deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 4/208:31 am
ORD
- BOS
1 stop4h 47m
JetBlue
Deal found 2/26![JetBlue logo]()
$230
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/286:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 2/25![United Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/79:20 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Sun 3/89:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/25![United Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/133:51 pm
BOS
- LSE
1 stop8h 45m
American Airlines
Thu 3/1911:34 am
LSE
- BOS
1 stop10h 27m
American Airlines
Deal found 2/25![American Airlines logo]()
$308
This Sun Country Air deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 2/25![Sun Country Air logo]()
$319
This Delta deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:30 am
BOS
- ATW
1 stop6h 02m
Delta
Wed 4/1512:05 pm
ATW
- BOS
1 stop6h 30m
Delta
Deal found 2/27![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:23 pm
BOS
- MKE
1 stop5h 20m
United Airlines
Wed 3/2511:00 am
MKE
- BOS
1 stop5h 19m
United Airlines
Deal found 2/26![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:16 pm
BOS
- GRB
1 stop5h 16m
American Airlines
Wed 3/185:00 am
GRB
- BOS
1 stop4h 46m
American Airlines
Deal found 2/28![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
2 stops8h 02m
United Airlines
Mon 6/89:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/27![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/273:10 pm
BOS
- GRB
1 stop7h 52m
Delta
Fri 4/35:17 pm
GRB
- BOS
1 stop5h 36m
Delta
Deal found 2/25![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:35 am
BOS
- MSP
1 stop5h 10m
Southwest
Tue 7/77:55 am
MSP
- BOS
1 stop4h 55m
Southwest
Deal found 2/26![Southwest logo]()
$379
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/123:51 pm
BOS
- LSE
1 stop8h 45m
American Airlines
Mon 3/1611:34 am
LSE
- BOS
1 stop11h 31m
American Airlines
Deal found 2/25![American Airlines logo]()
$332
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 3/299:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/28![United Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:40 am
BOS
- ATW
1 stop6h 31m
Delta
Tue 7/75:20 pm
ATW
- BOS
1 stop5h 12m
Delta
Deal found 2/26![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:35 am
BOS
- MSP
1 stop8h 35m
Southwest
Sun 6/710:35 am
MSP
- BOS
1 stop8h 00m
Southwest
Deal found 2/27![Southwest logo]()
$399
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Sun 3/296:52 am
BOS
- CWA
1 stop5h 09m
American Airlines
Sun 4/55:20 am
CWA
- BOS
1 stop5h 18m
American Airlines
Deal found 2/25![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:05 am
BOS
- MSN
1 stop4h 49m
Delta
Tue 8/115:50 pm
MSN
- BOS
1 stop4h 42m
Delta
Deal found 2/26![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:00 am
BOS
- DLH
1 stop5h 43m
United Airlines
Mon 3/306:42 pm
DLH
- BOS
1 stop5h 17m
United Airlines
Deal found 2/26![United Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:45 am
BOS
- MSP
1 stop10h 35m
Southwest
Sun 7/1910:35 am
MSP
- BOS
1 stop8h 00m
Southwest
Deal found 2/27![Southwest logo]()
$434
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/295:30 am
BOS
- ATW
1 stop6h 02m
Delta
Fri 4/312:06 pm
ATW
- BOS
1 stop6h 28m
Delta
Deal found 2/25![Delta logo]()
$302
Last-minute flights from Boston to WisconsinDiscover last-minute flight deals from Boston to Wisconsin. Data last updated March 1, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Wisconsin. Data last updated March 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Tue 3/310:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/27![JetBlue logo]()
$140
This KAYAK deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/25![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 3/47:30 am
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/27![United Airlines logo]()
$145
This Super.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/1110:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/25![JetBlue logo]()
$143
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:15 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Fri 4/36:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/27![United Airlines logo]()
$131
This American Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:09 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Tue 3/247:40 pm
ORD
- BOS
Nonstop2h 21m
American Airlines
Deal found 2/26![American Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:25 pm
BOS
- ORD
Nonstop3h 06m
Delta
Tue 3/247:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 2/26![Delta logo]()
$136
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/184:25 pm
BOS
- ORD
Nonstop3h 06m
Delta
Mon 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/28![Delta logo]()
$141
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Mon 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/28![Delta logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 2/26![United Airlines logo]()
$146
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/27![United Airlines logo]()
$134
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.
Mon 3/306:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Thu 4/27:40 pm
ORD
- BOS
Nonstop2h 21m
American Airlines
Deal found 3/1![American Airlines logo]()
$142
One-way flights from Boston to WisconsinSearch for one-way flight options from Boston to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 1, 2026.
Search for one-way flight options from Boston to Wisconsin. Find affordable one-way fares based on user searches. Data last updated March 1, 2026.
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2012:10 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/27![United Airlines logo]()
$64
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- ORD
2 stops10h 30m
Southwest
Deal found 2/28![Southwest logo]()
$65
This Super.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 2/25![JetBlue logo]()
$66
This United Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:05 am
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 2/26![United Airlines logo]()
$67
This Cheapflightsfares deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/27![JetBlue logo]()
$68
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Deal found 2/28![Southwest logo]()
$69
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$70
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 3/1![Southwest logo]()
$71
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:15 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/27![United Airlines logo]()
$73
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:20 am
BOS
- ORD
2 stops11h 10m
Southwest
Deal found 2/27![Southwest logo]()
$74
This United Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/27![United Airlines logo]()
$75
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/811:12 am
BOS
- MSP
Nonstop3h 18m
Sun Country Air
Deal found 2/25![Sun Country Air logo]()
$89
Find flight deals from Boston to Wisconsin
Keep the following information in mind while searching for Boston to Wisconsin flight deals. Data was last updated March 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $128 (Southwest) |
One-way from | $64 (United Airlines) |
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 Boston 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 1, 2026.
Use the filters below to find and compare flights from Boston to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/9
7:00 am-9:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 4/13
7:30 am-11:01 am
Nonstop2h 31m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 4/14
7:35 pm-9:39 pm
Nonstop3h 04m
Chicago O'Hare Intl
Thu 4/16
8:31 am-2:18 pm
1 stop4h 47m
$171
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/4
12:35 pm-2:41 pm
Nonstop3h 06m
Chicago O'Hare Intl
Fri 3/6
2:35 pm-8:15 pm
1 stop4h 40m
$171
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/10
6:00 am-10:51 am
1 stop5h 51m
Chicago O'Hare Intl
Tue 3/10
6:05 pm-9:28 pm
Nonstop2h 23m
$171
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/11
8:20 pm-10:16 pm
Nonstop2h 56m
Chicago O'Hare Intl
Fri 3/13
7:00 am-10:25 am
Nonstop2h 25m
$181
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 3/18
4:50 pm-6:40 pm
Nonstop2h 50m
Milwaukee-Mitchell
Mon 3/23
7:25 pm-10:41 pm
Nonstop2h 16m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 4/17
7:55 am-10:00 am
Nonstop3h 05m
Chicago O'Hare Intl
Tue 4/21
7:59 pm-11:27 pm
Nonstop2h 28m
$207
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Thu 5/7
5:40 am-9:50 am
1 stop5h 10m
Milwaukee-Mitchell
Mon 5/11
3:30 pm-9:50 pm
1 stop5h 20m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sun 5/31
6:15 am-9:39 am
Nonstop2h 24m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 3/7
9:20 am-11:25 am
Nonstop3h 05m
Chicago O'Hare Intl
Sun 3/8
9:15 pm-12:35 am
Nonstop2h 20m
$226
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Boston with our price prediction graph.
BOS-ORD
BOS-MSP
BOS-MKE
BOS-ATW
BOS-GRB
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 Boston to Wisconsin
BOS-USWI
BOS-ORD
BOS-MSP
BOS-MKE
BOS-ATW
What is the cheapest month to book a flight from Boston to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $98). Flying from Boston 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 BOS to WI?
Find hourly flight availability from Boston 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 1, 2026.
It’s optimal to fly from Boston to Wisconsin at noon. By choosing this option you can save up to 50% on the cost of your flight, compared to a flight in the evening.
What is the cheapest day to fly from Boston to Wisconsin?
Use this chart to determine the cheapest time to fly round-trip from Boston to Wisconsin. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Boston 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 Boston to Wisconsin
Explore weekly flight availability from Boston 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 1, 2026.
The most flights from BOS to USWI are scheduled on a Friday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 1, 2026.
Read through reviews of airlines operating flights from Boston to Wisconsin, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Boston to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Boston 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 Boston to Wisconsin by cabin class
Find flights from Boston to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Wisconsin flights
Browse other Boston and Wisconsin flight options. Last updated on March 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Wisconsin flights
Consider these flights traveling from Boston to Wisconsin.
Top 5 airlines flying from Boston to Wisconsin
Discover the top 5 airlines that operate flights from Boston 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 1, 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% |