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

Wednesday, July 22nd, 2026

4 round-trip options

Returning
Thu, Jul 30, 20268 Day Trip
$277 USD
Returning
Fri, Jul 31, 20269 Day Trip
$387 USD
Returning
Sun, Aug 2, 202611 Day Trip
$387 USD
Returning
Mon, Aug 3, 202612 Day Trip
$387 USD