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 21st, 2026

4 round-trip options

Returning
Wed, Jul 29, 20268 Day Trip
$336 USD
Returning
Thu, Jul 30, 20269 Day Trip
$272 USD
Returning
Sat, Aug 1, 202611 Day Trip
$382 USD
Returning
Sun, Aug 2, 202612 Day Trip
$382 USD