Chicago (ORD) to San Juan (SJU) flight deal in economy from $307

Saturday, July 18th, 2026

10 round-trip options

Returning
Thu, Jul 23, 20265 Day Trip
$504 USD
Returning
Fri, Jul 24, 20266 Day Trip
$479 USD
Returning
Sat, Jul 25, 20267 Day Trip
$482 USD
Returning
Sun, Jul 26, 20268 Day Trip
$473 USD
Returning
Mon, Jul 27, 20269 Day Trip
$446 USD
Returning
Tue, Jul 28, 202610 Day Trip
$486 USD
Returning
Wed, Jul 29, 202611 Day Trip
$525 USD
Returning
Thu, Jul 30, 202612 Day Trip
$545 USD
Returning
Fri, Jul 31, 202613 Day Trip
$545 USD
Returning
Sat, Aug 1, 202614 Day Trip
$473 USD