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

Friday, July 31st, 2026

4 round-trip options

Returning
Sat, Aug 8, 20268 Day Trip
$432 USD
Returning
Sun, Aug 9, 20269 Day Trip
$472 USD
Returning
Tue, Aug 11, 202611 Day Trip
$477 USD
Returning
Wed, Aug 12, 202612 Day Trip
$432 USD