Chicago (ORD) to San Juan (SJU) flight deal in business from $468

Thursday, December 24th, 2026

7 round-trip options

Returning
Tue, Dec 29, 20265 Day Trip
$1,072 USD
Returning
Wed, Dec 30, 20266 Day Trip
$1,089 USD
Returning
Thu, Dec 31, 20267 Day Trip
$1,078 USD
Returning
Fri, Jan 1, 20278 Day Trip
$1,413 USD
Returning
Sat, Jan 2, 20279 Day Trip
$1,427 USD
Returning
Sun, Jan 3, 202710 Day Trip
$1,413 USD
Returning
Mon, Jan 4, 202711 Day Trip
$1,229 USD