Chicago (ORD) to San José (SJO) flight deal in economy from $346

Good Availability
47% of dates checked are available within 10% of the lowest price

Friday, July 31st, 2026

5 round-trip options

Returning
Fri, Aug 7, 20267 Day Trip
$1,546 USD
Returning
Sat, Aug 8, 20268 Day Trip
$1,546 USD
Returning
Sun, Aug 9, 20269 Day Trip
$913 USD
Returning
Thu, Aug 13, 202613 Day Trip
$1,463 USD
Returning
Fri, Aug 14, 202614 Day Trip
$1,491 USD