$154+ Cheap flights from San José (SJO) 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
May 17 — May 241
Round-trip
1 adult, Economy
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Cheapest flights from San José to WisconsinExplore the most affordable flight options available from San José 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 San José to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
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 5/81:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$331
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.
Fri 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$340
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.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/119:20 am
ORD
- SJO
3 stops27h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$348
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Mon 5/182:35 am
ORD
- SJO
1 stop22h 24m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$349
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:38 pm
SJO
- ORD
2 stops9h 29m
Spirit Airlines
Wed 4/297:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$352
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Thu 5/145:30 pm
ORD
- SJO
2 stops19h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$357
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.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sat 5/301:18 pm
ORD
- SJO
1 stop23h 27m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$358
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 6/19:35 am
SJO
- ORD
2 stops21h 20m
Frontier
Sat 6/65:11 pm
ORD
- SJO
1 stop16h 08m
Frontier
Deal found 4/14![Frontier logo]()
$360
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Fri 5/155:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$361
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.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SJO
1 stop7h 40m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$365
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/185:30 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$366
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.
Thu 6/49:35 am
SJO
- MSP
1 stop11h 25m
Multiple Airlines
Sat 6/202:24 pm
MSP
- SJO
2 stops18h 56m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$430
Best flights from San José to WisconsinDiscover carefully curated flight deals from San José 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 San José 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 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.
Thu 5/71:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Sun 5/105:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$384
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:20 am
SJO
- ORD
1 stop21h 20m
Viva
Fri 7/171:30 am
ORD
- SJO
1 stop24h 45m
Viva
Deal found 4/12![Viva logo]()
$458
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.
Sat 5/301:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Sun 6/146:30 am
ORD
- SJO
1 stop17h 09m
United Airlines
Deal found 4/15![United Airlines logo]()
$470
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1410:05 am
SJO
- ORD
1 stop16h 55m
Copa Airlines
Mon 6/223:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:00 am
SJO
- MSP
2 stops12h 50m
Southwest
Mon 8/316:25 am
MSP
- SJO
2 stops13h 15m
Southwest
Deal found 4/13![Southwest logo]()
$592
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:00 pm
SJO
- MSP
2 stops26h 02m
Multiple Airlines
Mon 5/1111:40 am
MSP
- SJO
1 stop28h 38m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$649
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.
Sat 5/231:20 pm
SJO
- MKE
1 stop9h 39m
Delta
Thu 8/275:55 am
MKE
- SJO
1 stop7h 01m
Delta
Deal found 4/15![Delta logo]()
$651
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.
Thu 4/302:08 pm
SJO
- CWA
2 stops22h 35m
American Airlines
Sun 6/76:00 am
CWA
- SJO
2 stops17h 42m
American Airlines
Deal found 4/14![American Airlines logo]()
$689
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.
Sat 5/301:00 pm
SJO
- ORD
Nonstop5h 35m
United Airlines
Tue 6/99:21 pm
ORD
- SJO
1 stop13h 50m
United Airlines
Deal found 4/15![United Airlines logo]()
$470
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:57 pm
SJO
- ORD
1 stop19h 09m
Copa Airlines
Thu 6/113:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:55 pm
SJO
- ORD
1 stop19h 02m
Copa Airlines
Sun 7/193:21 pm
ORD
- SJO
1 stop17h 05m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Copa Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/214:10 am
SJO
- ORD
1 stop8h 56m
Copa Airlines
Mon 6/18:02 am
ORD
- SJO
1 stop11h 59m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$473
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 5/2111:13 am
SJO
- MKE
1 stop10h 32m
United Airlines
Mon 5/258:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/16![United Airlines logo]()
$536
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:00 am
SJO
- MSP
2 stops12h 35m
Southwest
Sun 5/317:20 am
MSP
- SJO
2 stops12h 40m
Southwest
Deal found 4/14![Southwest logo]()
$601
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1410:05 am
SJO
- ORD
1 stop16h 55m
Copa Airlines
Thu 6/183:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/12![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:00 am
SJO
- MSP
2 stops12h 20m
Southwest
Tue 9/227:00 am
MSP
- SJO
2 stops12h 40m
Southwest
Deal found 4/17![Southwest logo]()
$612
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 6/95:48 pm
SJO
- MSP
2 stops18h 50m
Multiple Airlines
Sun 6/148:50 am
MSP
- SJO
1 stop31h 21m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$690
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:19 pm
SJO
- ORD
1 stop18h 47m
Copa Airlines
Sat 5/303:21 pm
ORD
- SJO
1 stop18h 45m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
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.
Sat 5/161:00 pm
SJO
- MKE
1 stop17h 49m
United Airlines
Mon 6/110:46 am
MKE
- SJO
1 stop24h 25m
United Airlines
Deal found 4/13![United Airlines logo]()
$605
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:00 am
SJO
- MSP
2 stops9h 50m
Southwest
Fri 5/156:30 am
MSP
- SJO
2 stops13h 30m
Southwest
Deal found 4/14![Southwest logo]()
$623
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:47 am
SJO
- ORD
1 stop18h 13m
Copa Airlines
Sun 6/213:21 pm
ORD
- SJO
1 stop16h 51m
Copa Airlines
Deal found 4/16![Copa Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:07 am
SJO
- MSP
3 stops29h 31m
Multiple Airlines
Tue 6/99:35 am
MSP
- SJO
2 stops15h 05m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$704
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:25 pm
SJO
- MKE
1 stop8h 34m
United Airlines
Fri 5/1512:06 pm
MKE
- SJO
1 stop24h 49m
United Airlines
Deal found 4/17![United Airlines logo]()
$608
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:47 am
SJO
- ORD
1 stop18h 13m
Copa Airlines
Wed 6/173:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Deal found 4/14![Copa Airlines logo]()
$473
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.
Thu 5/149:00 am
SJO
- MSP
2 stops13h 00m
Southwest
Thu 5/218:05 am
MSP
- SJO
2 stops11h 55m
Southwest
Deal found 4/16![Southwest logo]()
$646
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 5/141:25 pm
SJO
- MKE
2 stops27h 07m
United Airlines
Thu 8/135:05 am
MKE
- SJO
2 stops39h 32m
United Airlines
Deal found 4/15![United Airlines logo]()
$617
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.
Sat 5/3012:30 am
SJO
- MKE
2 stops17h 21m
United Airlines
Sun 6/78:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/13![United Airlines logo]()
$618
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 5/259:00 am
SJO
- MSP
2 stops13h 20m
Southwest
Tue 6/27:10 am
MSP
- SJO
2 stops12h 50m
Southwest
Deal found 4/15![Southwest logo]()
$686
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.
Wed 5/2712:30 am
SJO
- MKE
2 stops11h 18m
United Airlines
Sun 5/318:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/13![United Airlines logo]()
$639
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:25 pm
SJO
- GRB
2 stops19h 36m
United Airlines
Tue 6/93:44 pm
GRB
- SJO
2 stops19h 27m
United Airlines
Deal found 4/12![United Airlines logo]()
$675
Last-minute flights from San José to WisconsinDiscover last-minute flight deals from San José to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Wisconsin. Data last updated April 17, 2026 and is based on user searches.
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:38 pm
SJO
- ORD
2 stops9h 29m
Spirit Airlines
Wed 4/297:15 pm
ORD
- SJO
1 stop17h 18m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$352
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.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/119:20 am
ORD
- SJO
3 stops27h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$348
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Thu 5/145:30 pm
ORD
- SJO
2 stops19h 15m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$357
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.
Thu 5/71:00 pm
SJO
- MSP
2 stops26h 02m
Multiple Airlines
Sun 5/104:30 pm
MSP
- SJO
1 stop23h 48m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$519
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 5/81:00 pm
SJO
- ORD
2 stops19h 54m
Spirit Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$331
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.
Fri 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Thu 5/147:33 pm
ORD
- SJO
1 stop17h 12m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$340
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Fri 5/155:05 am
ORD
- SJO
1 stop7h 40m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$361
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Mon 5/182:35 am
ORD
- SJO
1 stop22h 24m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$349
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Mon 5/185:30 pm
ORD
- SJO
1 stop22h 48m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$366
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.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sat 5/301:18 pm
ORD
- SJO
1 stop23h 27m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$358
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.
Thu 5/219:35 am
SJO
- ORD
1 stop12h 38m
Multiple Airlines
Sun 5/315:05 am
ORD
- SJO
1 stop7h 40m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$365
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:35 am
SJO
- MSP
2 stops22h 44m
Frontier
Thu 6/44:57 pm
MSP
- SJO
2 stops40h 22m
Frontier
Deal found 4/13![Frontier logo]()
$515
One-way flights from San José to WisconsinSearch for one-way flight options from San José to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from San José to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
SJO
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$154
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$160
This WAYA 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:00 pm
SJO
- ORD
1 stop9h 59m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$191
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.
Mon 5/111:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$192
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.
Sat 6/69:35 am
SJO
- MKE
1 stop21h 26m
Frontier
Deal found 4/15![Frontier logo]()
$194
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.
Sun 5/101:00 pm
SJO
- ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$195
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.
Thu 5/71:00 pm
SJO
- ORD
1 stop9h 15m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$196
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:18 pm
SJO
- ORD
1 stop18h 51m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$199
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:35 am
SJO
- MKE
1 stop21h 23m
Frontier
Deal found 4/13![Frontier logo]()
$231
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/171:00 pm
SJO
- MSP
3 stops43h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines 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 5/141:25 pm
SJO
- MKE
2 stops21h 06m
United Airlines
Deal found 4/16![United Airlines logo]()
$259
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.
Wed 5/137:55 am
SJO
- MKE
2 stops28h 16m
United Airlines
Deal found 4/16![United Airlines logo]()
$265
Find flight deals from San José to Wisconsin
Keep the following information in mind while searching for San José 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 | $331 (CheapOair) |
One-way from | $154 (Trip.com) |
Popular in | July |
Cheapest in | January |
Average price | $525 |
Cheapflights Fare Finder
Customize your flight search to find flights from San José 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 San José to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/7
1:00 pm-9:54 am
2 stops19h 54m
Chicago O'Hare Intl
Sun 5/10
5:05 am-11:45 am
1 stop7h 40m
$384
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 7/10
2:20 am-12:40 am
1 stop21h 20m
Chicago O'Hare Intl
Fri 7/17
1:30 am-1:15 am
1 stop24h 45m
$458
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Sun 6/14
6:30 am-10:39 pm
1 stop17h 09m
$470
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Tue 6/9
9:21 pm-10:11 am
1 stop13h 50m
$470
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Mon 6/22
3:21 pm-9:06 am
1 stop18h 45m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 6/3
5:57 pm-2:06 pm
1 stop19h 09m
Chicago O'Hare Intl
Thu 6/11
3:21 pm-7:12 am
1 stop16h 51m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 7/13
5:55 pm-1:57 pm
1 stop19h 02m
Chicago O'Hare Intl
Sun 7/19
3:21 pm-7:26 am
1 stop17h 05m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/21
4:10 am-2:06 pm
1 stop8h 56m
Chicago O'Hare Intl
Mon 6/1
8:02 am-7:01 pm
1 stop11h 59m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Thu 6/18
3:21 pm-9:06 am
1 stop18h 45m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/16
6:19 pm-2:06 pm
1 stop18h 47m
Chicago O'Hare Intl
Sat 5/30
3:21 pm-9:06 am
1 stop18h 45m
$473
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from San José to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from San José with our price prediction graph.
SJO-ORD
SJO-MKE
SJO-MSP
SJO-CWA
SJO-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 San José to Wisconsin
SJO-USWI
SJO-ORD
SJO-MKE
SJO-MSP
SJO-CWA
What is the cheapest month to book a flight from San José to Wisconsin?
Currently, May is the cheapest month in which you can book a flight from San José to Wisconsin (average of $256). Flying from San José to Wisconsin in October is currently the most expensive (average of $520). 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.
How much does it cost to fly round-trip from San José 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 San José to Wisconsin, such as United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Overall
7.4
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from San José 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 San José to Wisconsin
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Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
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San José and Wisconsin flights
Browse other San José and Wisconsin flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San José to Wisconsin flights
Consider these flights traveling from San José to Wisconsin.
Top 2 airlines flying from San José to Wisconsin
Discover the top 2 airlines that operate flights from San José 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$399 | Average$554 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$458 | Average$537 | FlexibilityNo cancel fee | On-time69% |