San Juan (SJU) to Chicago (ORD) flight deal in business from $706

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

Wednesday, June 10th, 2026

6 round-trip options

Returning
Mon, Jun 15, 20265 Day Trip
$1,791 USD
Returning
Tue, Jun 16, 20266 Day Trip
$1,879 USD
Returning
Thu, Jun 18, 20268 Day Trip
$1,787 USD
Returning
Sat, Jun 20, 202610 Day Trip
$1,720 USD
Returning
Tue, Jun 23, 202613 Day Trip
$1,792 USD
Returning
Wed, Jun 24, 202614 Day Trip
$1,853 USD