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

Sunday, December 27th, 2026

4 round-trip options

Returning
Fri, Jan 1, 20275 Day Trip
$1,056 USD
Returning
Sat, Jan 2, 20276 Day Trip
$1,056 USD
Returning
Sun, Jan 3, 20277 Day Trip
$1,056 USD
Returning
Mon, Jan 4, 20278 Day Trip
$892 USD