$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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 17 — May 241
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 17, 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 17, 2026.
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/66:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/13![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$150
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/14![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/610:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$153
This Expedia deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 4/266:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Wed 4/2910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This flygcity.se deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 16m
JetBlue
Deal found 4/14![JetBlue logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Thu 4/305:55 am
BOS
- ORD
1 stop16h 22m
Multiple Airlines
Mon 5/46:00 am
ORD
- BOS
1 stop26h 12m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$158
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/57:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/15![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:31 pm
BOS
- ORD
1 stop11h 08m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/14![Frontier logo]()
$160
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 17, 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 17, 2026.
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 6/309:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 4/13![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/65:30 am
BOS
- MKE
1 stop4h 20m
Delta
Wed 5/67:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/13![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 6/13:45 pm
BOS
- MKE
1 stop7h 30m
Southwest
Thu 6/45:15 pm
MKE
- BOS
1 stop4h 35m
Southwest
Deal found 4/16![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/115:35 pm
BOS
- GRB
1 stop5h 28m
American Airlines
Sat 5/2312:15 pm
GRB
- BOS
1 stop6h 43m
American Airlines
Deal found 4/16![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 9/58:10 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 9/86:20 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/14![United Airlines logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/710:45 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/107:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/15![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/307:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Sun 5/36:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 4/13![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sat 7/113:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/16![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/147:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Thu 5/217:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/14![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/26:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/16![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/612:30 pm
BOS
- ORD
Nonstop2h 57m
Delta
Sun 5/107:00 am
ORD
- BOS
1 stop6h 14m
Delta
Deal found 4/13![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 6/136:00 am
BOS
- MKE
1 stop6h 08m
United Airlines
Tue 6/161:30 pm
MKE
- BOS
1 stop5h 00m
United Airlines
Deal found 4/16![United Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/54:34 pm
BOS
- GRB
1 stop6h 24m
American Airlines
Wed 5/65:40 am
GRB
- BOS
1 stop4h 52m
American Airlines
Deal found 4/12![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 9/39:00 am
BOS
- MKE
Nonstop2h 44m
Delta
Mon 9/76:25 pm
MKE
- BOS
1 stop4h 07m
Delta
Deal found 4/12![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 9/246:00 am
BOS
- ORD
Nonstop2h 50m
United Airlines
Sun 9/276:00 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/16![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 9/107:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Sun 9/137:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 4/12![Delta logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 6/34:46 pm
BOS
- LSE
2 stops8h 20m
American Airlines
Wed 6/105:32 pm
LSE
- BOS
1 stop5h 42m
American Airlines
Deal found 4/15![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 7/67:42 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/13![United Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/13![Delta logo]()
$252
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/276:41 pm
BOS
- CWA
1 stop6h 14m
American Airlines
Tue 6/23:12 pm
CWA
- BOS
1 stop8h 03m
American Airlines
Deal found 4/14![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 8/157:05 am
BOS
- MSP
1 stop6h 05m
Southwest
Sat 8/225:30 am
MSP
- BOS
1 stop5h 55m
Southwest
Deal found 4/12![Southwest logo]()
$419
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 6/105:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 6/149:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/15![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 8/157:05 am
BOS
- MSP
1 stop6h 05m
Southwest
Sun 8/2311:20 am
MSP
- BOS
1 stop8h 05m
Southwest
Deal found 4/12![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/85:40 am
BOS
- MKE
1 stop4h 09m
Delta
Fri 5/87:50 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/13![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/185:40 am
BOS
- MSP
1 stop5h 20m
Southwest
Fri 5/224:55 pm
MSP
- BOS
1 stop5h 20m
Southwest
Deal found 4/15![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/307:00 am
BOS
- MKE
1 stop7h 34m
Delta
Sun 5/37:58 pm
MKE
- BOS
Nonstop2h 23m
Delta
Deal found 4/15![Delta logo]()
$262
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/28:28 pm
BOS
- MSN
Nonstop2h 47m
American Airlines
Mon 7/67:20 am
MSN
- BOS
Nonstop2h 33m
American Airlines
Deal found 4/16![American Airlines logo]()
$402
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/126:00 am
BOS
- MKE
1 stop6h 14m
United Airlines
Wed 7/1510:39 am
MKE
- BOS
1 stop4h 50m
United Airlines
Deal found 4/16![United Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 8/149:40 am
BOS
- MSP
1 stop6h 20m
Southwest
Thu 8/207:10 am
MSP
- BOS
1 stop8h 00m
Southwest
Deal found 4/16![Southwest logo]()
$419
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 9/57:00 am
BOS
- LSE
1 stop12h 02m
American Airlines
Mon 9/76:37 pm
LSE
- BOS
1 stop14h 47m
American Airlines
Deal found 4/16![American Airlines logo]()
$404
Last-minute flights from Boston to WisconsinDiscover last-minute flight deals from Boston to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/246:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Wed 4/291:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 4/13![American Airlines logo]()
$162
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 4/266:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Wed 4/2910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 4/12![Frontier logo]()
$180
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/12:25 pm
BOS
- MKE
Nonstop2h 36m
Multiple Airlines
Tue 5/59:56 am
MKE
- BOS
1 stop22h 16m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$174
This Priceline deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Fri 5/16:00 am
BOS
- MKE
1 stop11h 28m
Frontier
Mon 5/46:23 pm
MKE
- BOS
1 stop6h 08m
Frontier
Deal found 4/15![Frontier logo]()
$180
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/211:16 am
BOS
- MKE
1 stop22h 22m
Frontier
Wed 5/612:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$171
This Expedia deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/46:00 am
BOS
- MKE
1 stop12h 28m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/16![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/42:25 pm
BOS
- MKE
Nonstop2h 36m
Multiple Airlines
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$169
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/66:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Fri 5/812:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/13![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Fri 5/86:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Mon 5/1112:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/16![Frontier logo]()
$181
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
BOS
- MKE
1 stop6h 14m
Multiple Airlines
Tue 5/124:58 pm
MKE
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$164
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Wed 5/2012:09 pm
MKE
- BOS
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$151
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 17, 2026.
Search for one-way flight options from Boston to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/136:00 am
BOS
- MKE
1 stop6h 14m
Frontier
Deal found 4/14![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/14![Frontier logo]()
$76
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/14![JetBlue logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/2912:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$79
This KAYAK deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Tue 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/13![JetBlue logo]()
$80
This Super.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/12![JetBlue logo]()
$81
This CheapOair deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/1610:07 am
BOS
- MKE
1 stop23h 54m
Frontier
Deal found 4/15![Frontier logo]()
$82
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 4/14![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/15![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/127:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 4/16![Delta logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 4/226:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$85
This Trip.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 4/14![Frontier logo]()
$86
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Expedia) |
One-way from | $70 (Priceline) |
Popular in | November |
Cheapest in | September |
Average price | $443 |
Good round-trip deal | $153 or less |
Good one-way deal | $198 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 17, 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
Tue 6/23
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 6/30
9:15 am-12:57 pm
Nonstop2h 42m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/5
8:10 am-10:08 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 9/8
6:20 pm-9:55 pm
Nonstop2h 35m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/7
10:45 am-12:45 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/10
7:30 am-11:01 am
Nonstop2h 31m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sat 7/11
3:55 pm-7:30 pm
Nonstop2h 35m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 5/4
6:00 am-9:25 am
Nonstop2h 25m
$192
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Wed 5/6
5:30 am-8:50 am
1 stop4h 20m
Milwaukee-Mitchell
Wed 5/6
7:58 pm-11:21 pm
Nonstop2h 23m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/30
7:10 am-9:15 am
Nonstop3h 05m
Chicago O'Hare Intl
Sun 5/3
6:50 am-10:11 am
Nonstop2h 21m
$197
BostonMilwaukee
BOS - MKE
BOSMKE
Boston Logan Intl
Sat 6/13
6:00 am-11:08 am
1 stop6h 08m
Milwaukee-Mitchell
Tue 6/16
1:30 pm-7:30 pm
1 stop5h 00m
$205
Quickest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/24
6:00 am-7:50 am
Nonstop2h 50m
Chicago O'Hare Intl
Sun 9/27
6:00 am-9:24 am
Nonstop2h 24m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/26
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 7/6
7:42 pm-11:18 pm
Nonstop2h 36m
$220
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-GRB
BOS-LSE
BOS-CWA
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-GRB
BOS-LSE
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 17, 2026.
It’s optimal to fly from Boston to Wisconsin in the evening. By choosing this option you can save up to 38% 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 11, 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.
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 17, 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$273 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$404 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$269 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$176 | Average$456 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$438 | FlexibilityNo cancel fee | On-time71% |