$132+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Mar 13 — Mar 201
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 February 11, 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 February 11, 2026.
This Orbitz deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:35 pm
SJO
- ORD
2 stops11h 12m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$288
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Fri 2/271:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 3/18:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$289
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/1612:31 pm
SJO
- ORD
1 stop10h 10m
Spirit Airlines
Tue 4/215:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$290
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJO
1 stop15h 06m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$291
This Orbitz deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Wed 3/44:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/201:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 2/225:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$294
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Tue 3/315:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$295
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:31 pm
SJO
- ORD
1 stop10h 10m
Spirit Airlines
Tue 4/215:32 pm
ORD
- SJO
1 stop18h 50m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sat 2/214:43 pm
ORD
- SJO
1 stop19h 39m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$297
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/211:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 2/284:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$298
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Wed 3/185:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$299
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/41:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 3/84:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$301
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 February 11, 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 February 11, 2026.
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sat 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Wed 3/48:16 pm
ORD
- SJO
1 stop16h 06m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Tue 3/107:39 am
ORD
- SJO
Nonstop5h 17m
United Airlines
Deal found 2/9![United Airlines logo]()
$318
This Copa Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Tue 3/35:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Tue 3/103:22 pm
ORD
- SJO
1 stop7h 24m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:00 am
SJO
- MKE
1 stop12h 50m
Southwest
Sun 5/3111:45 am
MKE
- SJO
1 stop8h 15m
Southwest
Deal found 2/8![Southwest logo]()
$442
This Avianca deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:05 am
SJO
- MKE
2 stops16h 50m
Multiple Airlines
Thu 5/2810:41 am
MKE
- SJO
2 stops13h 59m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$452
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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
SJO
- CWA
2 stops16h 18m
American Airlines
Sun 4/265:40 am
CWA
- SJO
2 stops14h 27m
American Airlines
Deal found 2/8![American Airlines logo]()
$569
This CheapOair deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/271:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 3/712:44 pm
ORD
- SJO
2 stops22h 38m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$302
This Copa Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Tue 3/311:01 am
SJO
- ORD
1 stop13h 03m
Copa Airlines
Sun 3/83:22 pm
ORD
- SJO
1 stop17h 58m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:35 pm
SJO
- ORD
1 stop11h 24m
United Airlines
Sun 3/87:39 am
ORD
- SJO
Nonstop5h 17m
United Airlines
Deal found 2/9![United Airlines logo]()
$323
This Copa Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/268:48 am
SJO
- ORD
1 stop15h 16m
Copa Airlines
Thu 3/123:22 pm
ORD
- SJO
1 stop16h 43m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$326
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/1612:31 pm
SJO
- ORD
1 stop10h 10m
Spirit Airlines
Thu 4/235:32 pm
ORD
- SJO
1 stop18h 50m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/272:05 pm
SJO
- ORD
Nonstop5h 30m
United Airlines
Wed 4/88:51 am
ORD
- SJO
1 stop11h 46m
United Airlines
Deal found 2/7![United Airlines logo]()
$329
This Copa Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/275:50 am
SJO
- ORD
1 stop18h 14m
Copa Airlines
Sun 3/12:22 pm
ORD
- SJO
3 stops26h 24m
Copa Airlines
Deal found 2/10![Copa Airlines logo]()
$331
This Copa Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/95:46 am
SJO
- ORD
1 stop18h 27m
Copa Airlines
Mon 4/133:21 pm
ORD
- SJO
1 stop18h 44m
Copa Airlines
Deal found 2/9![Copa Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SJO
- MKE
1 stop12h 50m
Southwest
Thu 5/285:30 am
MKE
- SJO
1 stop7h 40m
Southwest
Deal found 2/8![Southwest logo]()
$447
This eDestinos deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/214:18 pm
SJO
- MSP
2 stops30h 40m
Multiple Airlines
Thu 4/2310:45 am
MSP
- SJO
1 stop29h 33m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$459
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 4/229:00 am
SJO
- MKE
1 stop12h 50m
Southwest
Thu 5/285:30 am
MKE
- SJO
1 stop7h 40m
Southwest
Deal found 2/8![Southwest logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/2412:19 pm
SJO
- MSP
1 stop26h 05m
Multiple Airlines
Sun 3/298:14 pm
MSP
- SJO
1 stop15h 28m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$484
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SJO
- MKE
2 stops13h 00m
Southwest
Sat 5/235:30 am
MKE
- SJO
1 stop14h 30m
Southwest
Deal found 2/8![Southwest logo]()
$465
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/112:22 pm
SJO
- CWA
2 stops22h 21m
American Airlines
Sat 8/226:25 pm
CWA
- SJO
2 stops19h 50m
American Airlines
Deal found 2/9![American Airlines logo]()
$577
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:13 am
SJO
- MKE
2 stops21h 47m
United Airlines
Wed 5/63:51 pm
MKE
- SJO
1 stop28h 46m
United Airlines
Deal found 2/8![United Airlines logo]()
$479
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Wed 4/12:42 pm
SJO
- MSP
2 stops21h 07m
Multiple Airlines
Sun 4/194:24 pm
MSP
- SJO
2 stops23h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:55 am
SJO
- MKE
2 stops25h 05m
United Airlines
Sun 5/108:30 pm
MKE
- SJO
2 stops16h 51m
United Airlines
Deal found 2/9![United Airlines logo]()
$480
This eDestinos deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:22 am
SJO
- MSP
2 stops39h 37m
Multiple Airlines
Mon 2/238:09 pm
MSP
- SJO
2 stops43h 11m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/121:05 pm
SJO
- MKE
1 stop23h 34m
United Airlines
Sat 3/145:10 pm
MKE
- SJO
1 stop27h 29m
United Airlines
Deal found 2/10![United Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/1611:38 am
SJO
- MSP
1 stop10h 33m
Multiple Airlines
Tue 3/316:21 pm
MSP
- SJO
2 stops17h 21m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$559
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/1711:38 am
SJO
- MSP
1 stop10h 28m
Multiple Airlines
Tue 3/316:21 pm
MSP
- SJO
2 stops17h 21m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$559
Last-minute flights from San José to WisconsinDiscover last-minute flight deals from San José to Wisconsin. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Wisconsin. Data last updated February 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sat 2/141:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sat 2/214:43 pm
ORD
- SJO
1 stop19h 39m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$297
This eDestinos deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Wed 4/85:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/7![Spirit Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/201:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 2/225:15 am
ORD
- SJO
1 stop7h 07m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$294
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/211:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 2/284:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$298
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Fri 2/271:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 3/18:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$289
This CheapOair deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/271:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 3/712:44 pm
ORD
- SJO
2 stops22h 38m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJO
1 stop15h 06m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$291
This Orbitz deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/281:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Wed 3/44:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$292
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/41:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Sun 3/84:43 pm
ORD
- SJO
2 stops18h 57m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$301
This Orbitz deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:35 pm
SJO
- ORD
2 stops11h 12m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJO
2 stops15h 24m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Wed 3/185:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$299
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:19 pm
SJO
- ORD
1 stop9h 58m
Spirit Airlines
Tue 3/315:05 am
ORD
- SJO
1 stop7h 09m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$295
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 February 11, 2026.
Search for one-way flight options from San José to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/1012:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$132
This Super.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$135
This Spirit deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/61:31 pm
SJO
- ORD
1 stop10h 16m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$141
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sat 3/147:58 am
SJO
- ORD
1 stop9h 33m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/61:31 pm
SJO
- ORD
1 stop30h 38m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Sat 3/71:31 pm
SJO
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/912:31 pm
SJO
- ORD
1 stop21h 05m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$149
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 3/127:05 am
SJO
- ORD
1 stop8h 51m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SJO
- MKE
1 stop12h 50m
Southwest
Deal found 2/9![Southwest logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/912:31 pm
SJO
- MSP
3 stops34h 26m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/159:00 am
SJO
- MKE
1 stop12h 50m
Southwest
Deal found 2/9![Southwest logo]()
$242
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sat 2/148:07 am
SJO
- MSP
1 stop15h 31m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$274
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $288 (Orbitz) |
One-way from | $132 (Super.com) |
Popular in | October |
Cheapest in | April |
Average price | $501 |
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 February 11, 2026.
Use the filters below to find and compare flights from San José to Wisconsin that are best for you.
Fly from
San José
Fly to
Wisconsin
Route
Depart
Return
Price
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 2/28
1:31 pm-9:13 pm
1 stop7h 42m
Chicago O'Hare Intl
Wed 3/4
8:16 pm-12:22 pm
1 stop16h 06m
$296
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 2/27
1:31 pm-9:13 pm
1 stop7h 42m
Chicago O'Hare Intl
Sat 3/7
12:44 pm-11:22 am
2 stops22h 38m
$302
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 3/6
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Tue 3/10
7:39 am-11:56 am
Nonstop5h 17m
$318
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 3/3
5:50 am-12:04 am
1 stop18h 14m
Chicago O'Hare Intl
Tue 3/10
3:22 pm-9:46 pm
1 stop7h 24m
$320
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 3/3
11:01 am-12:04 am
1 stop13h 03m
Chicago O'Hare Intl
Sun 3/8
3:22 pm-8:20 am
1 stop17h 58m
$320
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 3/4
12:35 pm-11:59 pm
1 stop11h 24m
Chicago O'Hare Intl
Sun 3/8
7:39 am-11:56 am
Nonstop5h 17m
$323
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 2/26
8:48 am-12:04 am
1 stop15h 16m
Chicago O'Hare Intl
Thu 3/12
3:22 pm-7:05 am
1 stop16h 43m
$326
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 4/16
12:31 pm-11:41 pm
1 stop10h 10m
Chicago O'Hare Intl
Thu 4/23
5:32 pm-11:22 am
1 stop18h 50m
$329
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 2/27
2:05 pm-7:35 pm
Nonstop5h 30m
Chicago O'Hare Intl
Wed 4/8
8:51 am-7:37 pm
1 stop11h 46m
$329
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 2/27
5:50 am-12:04 am
1 stop18h 14m
Chicago O'Hare Intl
Sun 3/1
2:22 pm-4:46 pm
3 stops26h 24m
$331
Showing 1-10 of 54 results
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
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 $530). 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.
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 February 11, 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.
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Food
6.6
Reviews
1 / 20
6.0
GoodGerry,Jan 2026
YVR - DEN
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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Complete your trip
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San José and Wisconsin flights
Browse other San José and Wisconsin flight options. Last updated on February 11, 2026.
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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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$458 | Average$537 | FlexibilityNo cancel fee | On-time69% |