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

Tuesday, June 23rd, 2026

6 round-trip options

Returning
Sun, Jun 28, 20265 Day Trip
$964 USD
Returning
Mon, Jun 29, 20266 Day Trip
$960 USD
Returning
Wed, Jul 1, 20268 Day Trip
$1,016 USD
Returning
Fri, Jul 3, 202610 Day Trip
$986 USD
Returning
Mon, Jul 6, 202613 Day Trip
$939 USD
Returning
Tue, Jul 7, 202614 Day Trip
$825 USD