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

Monday, June 22nd, 2026

6 round-trip options

Returning
Sat, Jun 27, 20265 Day Trip
$1,087 USD
Returning
Sun, Jun 28, 20266 Day Trip
$1,128 USD
Returning
Tue, Jun 30, 20268 Day Trip
$1,060 USD
Returning
Thu, Jul 2, 202610 Day Trip
$1,159 USD
Returning
Sun, Jul 5, 202613 Day Trip
$1,087 USD
Returning
Mon, Jul 6, 202614 Day Trip
$1,010 USD