San José (SJO) to Chicago (ORD) flight deal in business from $860

Thursday, August 27th, 2026

9 round-trip options

Returning
Tue, Sep 1, 20265 Day Trip
$2,038 USD
Returning
Wed, Sep 2, 20266 Day Trip
$2,539 USD
Returning
Thu, Sep 3, 20267 Day Trip
$1,753 USD
Returning
Fri, Sep 4, 20268 Day Trip
$2,641 USD
Returning
Sat, Sep 5, 20269 Day Trip
$2,548 USD
Returning
Sun, Sep 6, 202610 Day Trip
$2,017 USD
Returning
Mon, Sep 7, 202611 Day Trip
$1,994 USD
Returning
Tue, Sep 8, 202612 Day Trip
$1,985 USD
Returning
Wed, Sep 9, 202613 Day Trip
$1,985 USD