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

Monday, July 27th, 2026

4 round-trip options

Returning
Tue, Aug 4, 20268 Day Trip
$362 USD
Returning
Wed, Aug 5, 20269 Day Trip
$362 USD
Returning
Fri, Aug 7, 202611 Day Trip
$362 USD
Returning
Sat, Aug 8, 202612 Day Trip
$362 USD