San Juan (SJU) to Chicago (ORD) flight deal in business from $468

Extremely Rare Availability
2% of dates checked are available within 10% of the lowest price

Friday, July 17th, 2026

10 round-trip options

Returning
Wed, Jul 22, 20265 Day Trip
$1,002 USD
Returning
Thu, Jul 23, 20266 Day Trip
$995 USD
Returning
Fri, Jul 24, 20267 Day Trip
$968 USD
Returning
Sat, Jul 25, 20268 Day Trip
$1,026 USD
Returning
Sun, Jul 26, 20269 Day Trip
$1,011 USD
Returning
Mon, Jul 27, 202610 Day Trip
$891 USD
Returning
Tue, Jul 28, 202611 Day Trip
$878 USD
Returning
Wed, Jul 29, 202612 Day Trip
$1,019 USD
Returning
Thu, Jul 30, 202613 Day Trip
$982 USD
Returning
Fri, Jul 31, 202614 Day Trip
$992 USD