San Juan (SJU) to Chicago (ORD) flight deal in economy from $307

Monday, December 28th, 2026

10 round-trip options

Returning
Sat, Jan 2, 20275 Day Trip
$612 USD
Returning
Sun, Jan 3, 20276 Day Trip
$621 USD
Returning
Mon, Jan 4, 20277 Day Trip
$607 USD
Returning
Tue, Jan 5, 20278 Day Trip
$607 USD
Returning
Wed, Jan 6, 20279 Day Trip
$628 USD
Returning
Thu, Jan 7, 202710 Day Trip
$612 USD
Returning
Fri, Jan 8, 202711 Day Trip
$637 USD
Returning
Sat, Jan 9, 202712 Day Trip
$612 USD
Returning
Sun, Jan 10, 202713 Day Trip
$607 USD
Returning
Mon, Jan 11, 202714 Day Trip
$607 USD