$70+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 29 — Jun 51
Round-trip
1 adult, Economy
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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 April 29, 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 April 29, 2026.
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/26![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 7/2110:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 4/28![JetBlue logo]()
$162
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$164
This Flysmarter deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/268:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/27![JetBlue logo]()
$165
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Wed 6/107:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/28![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:37 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Tue 6/26:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/28![American Airlines logo]()
$168
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:25 pm
BOS
- MKE
Nonstop2h 38m
Multiple Airlines
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$169
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Tue 6/21:50 pm
ORD
- BOS
1 stop10h 34m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Wed 6/31:29 pm
ORD
- BOS
1 stop10h 55m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$171
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 April 29, 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 April 29, 2026.
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/26![Delta logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Wed 6/39:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/27![United Airlines logo]()
$172
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:25 pm
BOS
- MKE
Nonstop2h 38m
JetBlue
Tue 5/124:58 pm
MKE
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/24![JetBlue logo]()
$187
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/225:20 pm
BOS
- MKE
1 stop7h 35m
Southwest
Wed 6/246:45 am
MKE
- BOS
1 stop4h 25m
Southwest
Deal found 4/29![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:21 am
BOS
- GRB
2 stops8h 00m
American Airlines
Tue 6/169:43 am
GRB
- BOS
2 stops7h 18m
American Airlines
Deal found 4/26![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 6/89:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/28![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:10 am
BOS
- MKE
Nonstop2h 43m
Delta
Wed 5/207:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/26![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Wed 6/107:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/28![United Airlines logo]()
$177
This Sun Country Air deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/210:35 am
BOS
- MSP
Nonstop3h 09m
Sun Country Air
Fri 8/145:50 am
MSP
- BOS
Nonstop2h 43m
Sun Country Air
Deal found 4/27![Sun Country Air logo]()
$394
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Sun 7/268:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/28![JetBlue logo]()
$205
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Sat 5/234:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/27![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/25. 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 8/2010:51 am
BOS
- ORD
Nonstop2h 51m
United Airlines
Sun 8/236:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 4/25![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:40 am
BOS
- MKE
1 stop4h 09m
Delta
Tue 6/97:20 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 4/28![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:10 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 8/166:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 4/27![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/109:10 am
BOS
- MKE
Nonstop2h 40m
Delta
Thu 6/115:56 pm
MKE
- BOS
1 stop4h 31m
Delta
Deal found 4/24![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/198:30 am
BOS
- ORD
1 stop5h 45m
United Airlines
Tue 5/196:15 pm
ORD
- BOS
1 stop4h 44m
United Airlines
Deal found 4/24![United Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:10 am
BOS
- LSE
1 stop7h 16m
American Airlines
Sat 7/255:41 pm
LSE
- BOS
1 stop5h 24m
American Airlines
Deal found 4/28![American Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:34 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Mon 10/266:00 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/26![United Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 6/25:05 am
BOS
- CWA
1 stop5h 16m
American Airlines
Tue 6/306:00 am
CWA
- BOS
2 stops9h 35m
American Airlines
Deal found 4/25![American Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Sun 8/307:35 pm
MKE
- BOS
Nonstop2h 19m
Delta
Deal found 4/27![Delta logo]()
$262
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 8/26:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/28![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:36 pm
BOS
- CWA
1 stop6h 19m
American Airlines
Sat 5/309:51 am
CWA
- BOS
2 stops9h 17m
American Airlines
Deal found 4/29![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:40 am
BOS
- MSP
1 stop5h 20m
Southwest
Mon 6/15:20 pm
MSP
- BOS
1 stop4h 50m
Southwest
Deal found 4/25![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/49:10 am
BOS
- MKE
Nonstop2h 43m
Delta
Tue 6/97:10 pm
MKE
- BOS
Nonstop2h 25m
Delta
Deal found 4/24![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/196:50 pm
BOS
- MSP
1 stop5h 25m
Southwest
Tue 6/235:25 am
MSP
- BOS
2 stops7h 20m
Southwest
Deal found 4/24![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:10 am
BOS
- MKE
Nonstop2h 43m
Delta
Thu 5/1411:33 am
MKE
- BOS
Nonstop2h 26m
Delta
Deal found 4/27![Delta logo]()
$272
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:00 am
BOS
- LSE
1 stop5h 22m
American Airlines
Sun 5/315:34 pm
LSE
- BOS
1 stop5h 41m
American Airlines
Deal found 4/27![American Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:40 am
BOS
- MSP
2 stops8h 50m
Southwest
Tue 9/158:00 am
MSP
- BOS
2 stops7h 10m
Southwest
Deal found 4/27![Southwest logo]()
$428
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:00 pm
BOS
- MKE
1 stop5h 34m
United Airlines
Tue 6/235:29 pm
MKE
- BOS
1 stop4h 47m
United Airlines
Deal found 4/28![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:30 am
BOS
- MKE
1 stop4h 20m
Delta
Wed 7/1511:35 am
MKE
- BOS
Nonstop2h 30m
Delta
Deal found 4/28![Delta logo]()
$292
Last-minute flights from Boston to WisconsinDiscover last-minute flight deals from Boston to Wisconsin. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Wisconsin. Data last updated April 29, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/26![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:25 pm
BOS
- MKE
Nonstop2h 38m
Multiple Airlines
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$169
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$169
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Fri 5/2910:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 4/27![Delta logo]()
$172
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:37 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Tue 6/26:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/28![American Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Tue 6/21:50 pm
ORD
- BOS
1 stop10h 34m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sat 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/27![JetBlue logo]()
$162
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/28![Delta logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Wed 6/31:29 pm
ORD
- BOS
1 stop10h 55m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$171
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 April 29, 2026.
Search for one-way flight options from Boston to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Frontier deal was found by Cheapflights users on 4/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/25![Frontier logo]()
$70
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/29![JetBlue logo]()
$82
This Super.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/27![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 4/28![Delta logo]()
$84
This Super.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/28![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/29![JetBlue logo]()
$88
This Super.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/116:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/24![Frontier logo]()
$89
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/225:00 am
BOS
- ORD
Nonstop2h 58m
American Airlines
Deal found 4/28![American Airlines logo]()
$89
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/28![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Deal found 4/28![Frontier logo]()
$90
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/162:51 pm
BOS
- MKE
Nonstop2h 38m
JetBlue
Deal found 4/28![JetBlue logo]()
$93
This Super.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/28![JetBlue logo]()
$93
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (CheapOair) |
One-way from | $70 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $439 |
Good round-trip deal | $154 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from 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 April 29, 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
Cheapest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/23
5:30 pm-7:33 pm
Nonstop3h 03m
Chicago O'Hare Intl
Sun 5/24
7:00 am-10:35 am
Nonstop2h 35m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 6/3
9:26 pm-12:59 am
Nonstop2h 33m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/4
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 6/8
9:26 pm-12:59 am
Nonstop2h 33m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/3
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Wed 6/10
7:40 pm-11:16 pm
Nonstop2h 36m
$177
Quickest round-trip
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Mon 5/11
2:25 pm-4:03 pm
Nonstop2h 38m
Milwaukee-Mitchell
Tue 5/12
4:58 pm-8:13 pm
Nonstop2h 15m
$187
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 5/13
9:10 am-10:53 am
Nonstop2h 43m
Milwaukee-Mitchell
Wed 5/20
7:50 pm-11:13 pm
Nonstop2h 23m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/20
10:51 am-12:42 pm
Nonstop2h 51m
Chicago O'Hare Intl
Sun 8/23
6:00 am-9:23 am
Nonstop2h 23m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/21
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Sat 5/23
4:30 pm-8:06 pm
Nonstop2h 36m
$192
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 6/3
5:40 am-8:49 am
1 stop4h 09m
Milwaukee-Mitchell
Tue 6/9
7:20 pm-10:45 pm
Nonstop2h 25m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/24
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Sun 7/26
8:20 pm-11:51 pm
Nonstop2h 31m
$205
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-MKE
BOS-ATW
BOS-MSP
BOS-LSE
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-MKE
BOS-ATW
BOS-MSP
How far ahead should I book a flight from Boston to Wisconsin?
The price you pay for your flight from Boston to Wisconsin may vary depending on when you book. For the best chance of a lower fare, look to book 89 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Boston to Wisconsin?
Currently, August is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $78). Flying from Boston to Wisconsin in March is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 April 29, 2026.
It’s optimal to fly from Boston to Wisconsin at noon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the morning.
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 April 25, 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. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Boston 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 29, 2026.
Read through reviews of airlines operating flights from Boston to Wisconsin, such as Southwest,Delta, andUnited Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
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 Boston 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 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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$271 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$443 | FlexibilityNo cancel fee | On-time71% |