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

Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Saturday, July 25th, 2026

10 round-trip options

Returning
Thu, Jul 30, 20265 Day Trip
$748 USD
Returning
Fri, Jul 31, 20266 Day Trip
$772 USD
Returning
Sat, Aug 1, 20267 Day Trip
$829 USD
Returning
Sun, Aug 2, 20268 Day Trip
$894 USD
Returning
Mon, Aug 3, 20269 Day Trip
$851 USD
Returning
Tue, Aug 4, 202610 Day Trip
$841 USD
Returning
Wed, Aug 5, 202611 Day Trip
$793 USD
Returning
Thu, Aug 6, 202612 Day Trip
$742 USD
Returning
Fri, Aug 7, 202613 Day Trip
$808 USD
Returning
Sat, Aug 8, 202614 Day Trip
$827 USD