Chicago (ORD) to San Juan (SJU) flight deal in business from $717

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

Sunday, June 14th, 2026

10 round-trip options

Returning
Fri, Jun 19, 20265 Day Trip
$1,059 USD
Returning
Sat, Jun 20, 20266 Day Trip
$1,059 USD
Returning
Sun, Jun 21, 20267 Day Trip
$1,234 USD
Returning
Mon, Jun 22, 20268 Day Trip
$1,229 USD
Returning
Tue, Jun 23, 20269 Day Trip
$1,158 USD
Returning
Wed, Jun 24, 202610 Day Trip
$1,160 USD
Returning
Thu, Jun 25, 202611 Day Trip
$1,054 USD
Returning
Fri, Jun 26, 202612 Day Trip
$1,169 USD
Returning
Sat, Jun 27, 202613 Day Trip
$1,109 USD
Returning
Sun, Jun 28, 202614 Day Trip
$1,271 USD