Chicago (ORD) to San Juan (SJU) flight deal in economy from $218

Extremely Rare Availability
4% of dates checked are available within 10% of the lowest price

Thursday, December 24th, 2026

7 round-trip options

Returning
Tue, Dec 29, 20265 Day Trip
$772 USD
Returning
Wed, Dec 30, 20266 Day Trip
$789 USD
Returning
Thu, Dec 31, 20267 Day Trip
$778 USD
Returning
Fri, Jan 1, 20278 Day Trip
$1,083 USD
Returning
Sat, Jan 2, 20279 Day Trip
$1,083 USD
Returning
Sun, Jan 3, 202710 Day Trip
$1,083 USD
Returning
Mon, Jan 4, 202711 Day Trip
$919 USD