Chicago (ORD) to San Juan (SJU) flight deal in business from $750

Thursday, October 8th, 2026

10 round-trip options

Returning
Tue, Oct 13, 2026•5 Day Trip
$1,153 USD
Returning
Wed, Oct 14, 2026•6 Day Trip
$967 USD
Returning
Thu, Oct 15, 2026•7 Day Trip
$1,351 USD
Returning
Fri, Oct 16, 2026•8 Day Trip
$1,165 USD
Returning
Sat, Oct 17, 2026•9 Day Trip
$1,169 USD
Returning
Sun, Oct 18, 2026•10 Day Trip
$1,662 USD
Returning
Mon, Oct 19, 2026•11 Day Trip
$1,532 USD
Returning
Tue, Oct 20, 2026•12 Day Trip
$1,505 USD
Returning
Wed, Oct 21, 2026•13 Day Trip
$1,485 USD
Returning
Thu, Oct 22, 2026•14 Day Trip
$1,481 USD