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

Wednesday, December 23rd, 2026

4 round-trip options

Returning
Mon, Dec 28, 20265 Day Trip
$973 USD
Returning
Wed, Dec 30, 20267 Day Trip
$1,073 USD
Returning
Fri, Jan 1, 20279 Day Trip
$1,600 USD
Returning
Sat, Jan 2, 202710 Day Trip
$1,566 USD