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

Sunday, December 6th, 2026

10 round-trip options

Returning
Fri, Dec 11, 20265 Day Trip
$814 USD
Returning
Sat, Dec 12, 20266 Day Trip
$814 USD
Returning
Sun, Dec 13, 20267 Day Trip
$814 USD
Returning
Mon, Dec 14, 20268 Day Trip
$814 USD
Returning
Tue, Dec 15, 20269 Day Trip
$814 USD
Returning
Wed, Dec 16, 202610 Day Trip
$835 USD
Returning
Thu, Dec 17, 202611 Day Trip
$934 USD
Returning
Fri, Dec 18, 202612 Day Trip
$1,008 USD
Returning
Sat, Dec 19, 202613 Day Trip
$1,192 USD
Returning
Sun, Dec 20, 202614 Day Trip
$1,119 USD