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

Thursday, July 16th, 2026

4 round-trip options

Returning
Fri, Jul 24, 20268 Day Trip
$386 USD
Returning
Sat, Jul 25, 20269 Day Trip
$436 USD
Returning
Mon, Jul 27, 202611 Day Trip
$436 USD
Returning
Tue, Jul 28, 202612 Day Trip
$432 USD