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

Saturday, July 18th, 2026

4 round-trip options

Returning
Sun, Jul 26, 20268 Day Trip
$386 USD
Returning
Mon, Jul 27, 20269 Day Trip
$386 USD
Returning
Wed, Jul 29, 202611 Day Trip
$336 USD
Returning
Thu, Jul 30, 202612 Day Trip
$336 USD