Chicago (ORD) to San Juan (SJU) flight deal in business from $717

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

Tuesday, June 23rd, 2026

10 round-trip options

Returning
Sun, Jun 28, 20265 Day Trip
$1,078 USD
Returning
Mon, Jun 29, 20266 Day Trip
$959 USD
Returning
Tue, Jun 30, 20267 Day Trip
$917 USD
Returning
Wed, Jul 1, 20268 Day Trip
$1,015 USD
Returning
Thu, Jul 2, 20269 Day Trip
$968 USD
Returning
Fri, Jul 3, 202610 Day Trip
$897 USD
Returning
Sat, Jul 4, 202611 Day Trip
$897 USD
Returning
Sun, Jul 5, 202612 Day Trip
$1,092 USD
Returning
Mon, Jul 6, 202613 Day Trip
$978 USD
Returning
Tue, Jul 7, 202614 Day Trip
$961 USD