Chicago (ORD) to San Juan (SJU) flight deal in economy from $237

Extremely Rare Availability
2% of dates checked are available within 10% of the lowest price

Tuesday, July 14th, 2026

4 round-trip options

Returning
Wed, Jul 22, 20268 Day Trip
$286 USD
Returning
Thu, Jul 23, 20269 Day Trip
$286 USD
Returning
Sat, Jul 25, 202611 Day Trip
$386 USD
Returning
Sun, Jul 26, 202612 Day Trip
$386 USD