$230+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jul 6 — Jul 131
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 June 6, 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 June 6, 2026.
This eDestinos deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/154:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Sat 10/172:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$379
This Cheapflightsfares deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/12:02 pm
SJO
- ORD
1 stop8h 42m
JetBlue
Tue 9/87:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/3![JetBlue logo]()
$388
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 6/169:55 am
ORD
- SJO
1 stop13h 05m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$394
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Tue 6/169:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 6/1![Air Canada logo]()
$420
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Sat 6/139:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 6/1![Air Canada logo]()
$422
This Booking.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Thu 6/46:22 pm
ORD
- SJO
2 stops27h 13m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$432
This Booking.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 6/169:55 am
ORD
- SJO
1 stop13h 05m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$433
This Volaris deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 9/14:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Mon 9/142:53 am
ORD
- SJO
1 stop22h 06m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:25 pm
SJO
- MKE
1 stop9h 27m
Delta
Sun 10/45:30 am
MKE
- SJO
1 stop7h 24m
Delta
Deal found 6/1![Delta logo]()
$506
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:00 am
SJO
- MKE
1 stop12h 20m
Southwest
Mon 11/25:10 am
MKE
- SJO
1 stop8h 05m
Southwest
Deal found 6/1![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/151:25 pm
SJO
- MKE
1 stop9h 27m
Delta
Mon 9/215:30 am
MKE
- SJO
1 stop7h 24m
Delta
Deal found 6/4![Delta logo]()
$516
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/2212:44 pm
SJO
- MKE
1 stop9h 52m
United Airlines
Mon 11/27:00 pm
MKE
- SJO
2 stops16h 25m
United Airlines
Deal found 6/2![United Airlines logo]()
$519
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 June 6, 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 June 6, 2026.
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/25:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Thu 8/63:21 pm
ORD
- SJO
1 stop18h 43m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/227:55 am
SJO
- MKE
2 stops22h 12m
United Airlines
Mon 11/27:00 pm
MKE
- SJO
2 stops16h 25m
United Airlines
Deal found 6/2![United Airlines logo]()
$519
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:00 am
SJO
- MSP
2 stops11h 40m
Southwest
Tue 9/87:15 am
MSP
- SJO
2 stops12h 25m
Southwest
Deal found 6/5![Southwest logo]()
$612
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/1612:50 pm
SJO
- CWA
2 stops19h 36m
American Airlines
Sun 8/304:40 pm
CWA
- SJO
2 stops20h 46m
American Airlines
Deal found 6/2![American Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/151:25 pm
SJO
- GRB
1 stop8h 04m
Delta
Thu 9/245:30 am
GRB
- SJO
1 stop7h 24m
Delta
Deal found 6/4![Delta logo]()
$693
This Faresmojo deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:19 pm
SJO
- MSP
1 stop18h 41m
JetBlue
Sun 6/148:10 pm
MSP
- SJO
1 stop16h 44m
JetBlue
Deal found 6/1![JetBlue logo]()
$753
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:00 am
SJO
- MSP
2 stops15h 02m
Multiple Airlines
Fri 9/252:40 pm
MSP
- SJO
3 stops25h 45m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$786
This Copa Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:58 am
SJO
- ORD
1 stop20h 07m
Copa Airlines
Thu 11/57:35 am
ORD
- SJO
1 stop11h 00m
Copa Airlines
Deal found 6/1![Copa Airlines logo]()
$473
This Copa Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 11/110:26 am
SJO
- ORD
1 stop26h 20m
Copa Airlines
Thu 11/52:13 pm
ORD
- SJO
1 stop18h 06m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$473
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/278:48 am
SJO
- ORD
1 stop15h 36m
Copa Airlines
Sat 10/313:13 pm
ORD
- SJO
1 stop18h 08m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:25 pm
SJO
- MKE
1 stop8h 14m
United Airlines
Wed 9/236:00 am
MKE
- SJO
2 stops14h 37m
United Airlines
Deal found 6/4![United Airlines logo]()
$580
This Copa Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/3010:03 am
SJO
- ORD
1 stop16h 57m
Copa Airlines
Mon 8/33:21 pm
ORD
- SJO
1 stop16h 49m
Copa Airlines
Deal found 6/2![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/228:45 am
SJO
- MSP
2 stops13h 05m
Southwest
Thu 7/305:50 am
MSP
- SJO
2 stops14h 50m
Southwest
Deal found 6/2![Southwest logo]()
$638
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/152:57 pm
SJO
- GRB
2 stops17h 38m
American Airlines
Thu 9/244:04 pm
GRB
- SJO
2 stops22h 53m
American Airlines
Deal found 6/4![American Airlines logo]()
$664
This Copa Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:49 pm
SJO
- ORD
1 stop12h 11m
Copa Airlines
Tue 7/213:21 pm
ORD
- SJO
1 stop18h 00m
Copa Airlines
Deal found 6/1![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/159:30 am
SJO
- MSP
2 stops9h 35m
Southwest
Tue 8/257:15 am
MSP
- SJO
2 stops12h 25m
Southwest
Deal found 6/2![Southwest logo]()
$645
This Copa Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/115:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Mon 8/173:21 pm
ORD
- SJO
1 stop20h 37m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:00 am
SJO
- MSP
2 stops11h 20m
Southwest
Fri 9/257:55 am
MSP
- SJO
2 stops11h 45m
Southwest
Deal found 6/1![Southwest logo]()
$664
This Copa Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/134:08 am
SJO
- ORD
1 stop19h 54m
Copa Airlines
Sat 9/193:20 pm
ORD
- SJO
1 stop16h 50m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:55 am
SJO
- DLH
2 stops14h 27m
United Airlines
Wed 10/217:45 am
DLH
- SJO
2 stops28h 53m
United Airlines
Deal found 6/3![United Airlines logo]()
$796
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/251:10 pm
SJO
- MSP
2 stops19h 55m
Southwest
Fri 8/77:55 am
MSP
- SJO
2 stops11h 45m
Southwest
Deal found 6/1![Southwest logo]()
$717
This Copa Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/105:55 pm
SJO
- ORD
1 stop19h 04m
Copa Airlines
Wed 8/198:02 am
ORD
- SJO
1 stop26h 02m
Copa Airlines
Deal found 6/5![Copa Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/158:45 am
SJO
- MSP
2 stops13h 05m
Southwest
Fri 7/317:05 am
MSP
- SJO
2 stops13h 35m
Southwest
Deal found 6/4![Southwest logo]()
$754
This Copa Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/2310:03 am
SJO
- MKE
2 stops20h 04m
Copa Airlines
Sun 9/610:19 am
MKE
- SJO
2 stops21h 51m
Copa Airlines
Deal found 6/5![Copa Airlines logo]()
$631
This Copa Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/234:08 am
SJO
- MKE
2 stops25h 59m
Copa Airlines
Sat 9/510:19 am
MKE
- SJO
2 stops23h 00m
Copa Airlines
Deal found 6/5![Copa Airlines logo]()
$631
Last-minute flights from San José to WisconsinDiscover last-minute flight deals from San José to Wisconsin. Data last updated June 6, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Wisconsin. Data last updated June 6, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:15 am
SJO
- ORD
1 stop10h 29m
Air Canada
Sat 6/133:40 pm
ORD
- SJO
1 stop29h 55m
Air Canada
Deal found 6/4![Air Canada logo]()
$388
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/74:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Sun 6/148:20 pm
ORD
- SJO
1 stop26h 40m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$433
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Tue 6/169:55 am
ORD
- SJO
1 stop13h 05m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$394
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:10 am
SJO
- MSP
1 stop11h 33m
Air Canada
Sun 6/147:00 am
MSP
- SJO
2 stops14h 35m
Air Canada
Deal found 6/1![Air Canada logo]()
$529
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:10 am
SJO
- MSP
2 stops36h 34m
Air Canada
Mon 6/151:05 pm
MSP
- SJO
2 stops33h 55m
Air Canada
Deal found 6/1![Air Canada logo]()
$601
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:15 am
SJO
- ORD
2 stops23h 30m
Air Canada
Tue 6/169:55 am
ORD
- SJO
1 stop13h 05m
Air Canada
Deal found 6/1![Air Canada logo]()
$420
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:10 am
SJO
- MSP
1 stop27h 59m
Air Canada
Sun 6/217:00 am
MSP
- SJO
2 stops14h 20m
Air Canada
Deal found 6/1![Air Canada logo]()
$621
This Air Canada deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/227:15 am
SJO
- MSP
2 stops27h 54m
Air Canada
Fri 10/301:10 pm
MSP
- SJO
1 stop10h 05m
Air Canada
Deal found 6/6![Air Canada logo]()
$603
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/257:07 am
SJO
- MSP
1 stop30h 07m
Multiple Airlines
Fri 10/307:55 am
MSP
- SJO
1 stop8h 16m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$629
This Orbitz deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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.
Tue 7/141:50 pm
SJO
- ORD
1 stop18h 00m
JetBlue
Sat 7/187:00 am
ORD
- SJO
1 stop6h 57m
JetBlue
Deal found 6/4![JetBlue logo]()
$448
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/1612:50 pm
SJO
- CWA
2 stops19h 36m
American Airlines
Sun 8/304:40 pm
CWA
- SJO
2 stops20h 46m
American Airlines
Deal found 6/2![American Airlines logo]()
$616
This Copa Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:37 pm
SJO
- MKE
2 stops16h 23m
Copa Airlines
Sat 8/17:23 pm
MKE
- SJO
2 stops16h 35m
Copa Airlines
Deal found 6/1![Copa Airlines logo]()
$631
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 June 6, 2026.
Search for one-way flight options from San José to Wisconsin. Find affordable one-way fares based on user searches. Data last updated June 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:05 pm
SJO
- ORD
1 stop8h 39m
JetBlue
Deal found 6/1![JetBlue logo]()
$230
This deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/199:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/5![Frontier logo]()
$232
This Volaris deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/14:15 pm
SJO
- ORD
1 stop18h 54m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$242
This Justfly.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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.
Sat 6/207:15 am
SJO
- ORD
2 stops23h 45m
Air Canada
Deal found 6/3![Air Canada logo]()
$255
This Viva deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/192:20 am
SJO
- ORD
1 stop21h 20m
Viva
Deal found 6/3![Viva logo]()
$264
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:45 am
SJO
- ORD
1 stop12h 25m
Frontier
Deal found 6/2![Frontier logo]()
$266
This Air Canada deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:10 am
SJO
- ORD
1 stop8h 48m
Air Canada
Deal found 6/1![Air Canada logo]()
$285
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Thu 7/169:35 am
SJO
- ORD
1 stop12h 35m
Frontier
Deal found 6/2![Frontier logo]()
$287
This Super.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:50 pm
SJO
- ORD
1 stop18h 00m
JetBlue
Deal found 6/2![JetBlue logo]()
$294
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:57 pm
SJO
- MKE
2 stops20h 51m
American Airlines
Deal found 6/1![American Airlines logo]()
$297
This Trip.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Sat 8/159:45 am
SJO
- MSP
1 stop24h 57m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:57 pm
SJO
- MKE
2 stops16h 04m
American Airlines
Deal found 6/1![American Airlines logo]()
$302
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 June 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (eDestinos) |
One-way from | $230 (Cheapflightsfares) |
Popular in | July |
Cheapest in | January |
Average price | $602 |
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 June 6, 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
Sun 8/2
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Thu 8/6
3:21 pm-9:04 am
1 stop18h 43m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 10/27
3:58 am-1:05 am
1 stop20h 07m
Chicago O'Hare Intl
Thu 11/5
7:35 am-6:35 pm
1 stop11h 00m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 11/1
10:26 am-12:46 pm
1 stop26h 20m
Chicago O'Hare Intl
Thu 11/5
2:13 pm-8:19 am
1 stop18h 06m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 10/27
8:48 am-1:24 am
1 stop15h 36m
Chicago O'Hare Intl
Sat 10/31
3:13 pm-8:21 am
1 stop18h 08m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 7/30
10:03 am-4:00 am
1 stop16h 57m
Chicago O'Hare Intl
Mon 8/3
3:21 pm-7:10 am
1 stop16h 49m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 7/7
2:49 pm-4:00 am
1 stop12h 11m
Chicago O'Hare Intl
Tue 7/21
3:21 pm-8:21 am
1 stop18h 00m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Tue 8/11
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Mon 8/17
3:21 pm-10:58 am
1 stop20h 37m
$473
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 9/13
4:08 am-1:02 am
1 stop19h 54m
Chicago O'Hare Intl
Sat 9/19
3:20 pm-7:10 am
1 stop16h 50m
$494
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 8/10
5:55 pm-1:59 pm
1 stop19h 04m
Chicago O'Hare Intl
Wed 8/19
8:02 am-9:04 am
1 stop26h 02m
$494
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/22
7:55 am-7:07 am
2 stops22h 12m
Milwaukee-Mitchell
Mon 11/2
7:00 pm-11:25 am
2 stops16h 25m
$519
Showing 1-10 of 53 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-MSP
SJO-CWA
SJO-MKE
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-MSP
SJO-CWA
SJO-MKE
What is the cheapest month to book a flight from San José to Wisconsin?
Currently, July is the cheapest month in which you can book a flight from San José to Wisconsin (average of $386). Flying from San José to Wisconsin in April is currently the most expensive (average of $596). 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 June 6, 2026.
Read through reviews of airlines operating flights from San José to Wisconsin, such as American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Food
6.4
Overall
7.1
Entertainment
6.9
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Crew
7.9
Food
6.4
Overall
7.1
Entertainment
6.9
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
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 June 6, 2026.
Popular flight searches
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San José to Wisconsin flights
Consider these flights traveling from San José to Wisconsin.
Top airline flying from San José to Wisconsin
Discover the top airline 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 June 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$638 | FlexibilityNo cancel fee | On-time71% |