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

Monday, July 27th, 2026

10 round-trip options

Returning
Sat, Aug 1, 20265 Day Trip
$711 USD
Returning
Sun, Aug 2, 20266 Day Trip
$792 USD
Returning
Mon, Aug 3, 20267 Day Trip
$633 USD
Returning
Tue, Aug 4, 20268 Day Trip
$684 USD
Returning
Wed, Aug 5, 20269 Day Trip
$676 USD
Returning
Thu, Aug 6, 202610 Day Trip
$701 USD
Returning
Fri, Aug 7, 202611 Day Trip
$673 USD
Returning
Sat, Aug 8, 202612 Day Trip
$631 USD
Returning
Sun, Aug 9, 202613 Day Trip
$671 USD
Returning
Mon, Aug 10, 202614 Day Trip
$584 USD