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

Sunday, June 28th, 2026

6 round-trip options

Returning
Fri, Jul 3, 20265 Day Trip
$1,051 USD
Returning
Sat, Jul 4, 20266 Day Trip
$969 USD
Returning
Mon, Jul 6, 20268 Day Trip
$1,001 USD
Returning
Wed, Jul 8, 202610 Day Trip
$1,070 USD
Returning
Sat, Jul 11, 202613 Day Trip
$1,025 USD
Returning
Sun, Jul 12, 202614 Day Trip
$1,023 USD