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

Tuesday, July 28th, 2026

10 round-trip options

Returning
Sun, Aug 2, 20265 Day Trip
$746 USD
Returning
Mon, Aug 3, 20266 Day Trip
$703 USD
Returning
Tue, Aug 4, 20267 Day Trip
$693 USD
Returning
Wed, Aug 5, 20268 Day Trip
$645 USD
Returning
Thu, Aug 6, 20269 Day Trip
$594 USD
Returning
Fri, Aug 7, 202610 Day Trip
$660 USD
Returning
Sat, Aug 8, 202611 Day Trip
$679 USD
Returning
Sun, Aug 9, 202612 Day Trip
$742 USD
Returning
Mon, Aug 10, 202613 Day Trip
$690 USD
Returning
Tue, Aug 11, 202614 Day Trip
$666 USD