Chicago (ORD) to San Juan (SJU) flight deal in economy from $237

Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Saturday, July 11th, 2026

7 round-trip options

Returning
Thu, Jul 16, 20265 Day Trip
$427 USD
Returning
Sat, Jul 18, 20267 Day Trip
$369 USD
Returning
Sun, Jul 19, 20268 Day Trip
$488 USD
Returning
Mon, Jul 20, 20269 Day Trip
$486 USD
Returning
Wed, Jul 22, 202611 Day Trip
$414 USD
Returning
Thu, Jul 23, 202612 Day Trip
$427 USD
Returning
Sat, Jul 25, 202614 Day Trip
$380 USD