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

Thursday, July 30th, 2026

10 round-trip options

Returning
Tue, Aug 4, 20265 Day Trip
$633 USD
Returning
Wed, Aug 5, 20266 Day Trip
$625 USD
Returning
Thu, Aug 6, 20267 Day Trip
$650 USD
Returning
Fri, Aug 7, 20268 Day Trip
$622 USD
Returning
Sat, Aug 8, 20269 Day Trip
$580 USD
Returning
Sun, Aug 9, 202610 Day Trip
$620 USD
Returning
Mon, Aug 10, 202611 Day Trip
$533 USD
Returning
Tue, Aug 11, 202612 Day Trip
$616 USD
Returning
Wed, Aug 12, 202613 Day Trip
$564 USD
Returning
Thu, Aug 13, 202614 Day Trip
$640 USD