San Juan (SJU) to Chicago (ORD) flight deal in business from $746

Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Sunday, October 18th, 2026

10 round-trip options

Returning
Fri, Oct 23, 2026•5 Day Trip
$1,376 USD
Returning
Sat, Oct 24, 2026•6 Day Trip
$1,152 USD
Returning
Sun, Oct 25, 2026•7 Day Trip
$1,105 USD
Returning
Mon, Oct 26, 2026•8 Day Trip
$1,109 USD
Returning
Tue, Oct 27, 2026•9 Day Trip
$1,105 USD
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Wed, Oct 28, 2026•10 Day Trip
$1,085 USD
Returning
Thu, Oct 29, 2026•11 Day Trip
$1,125 USD
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Fri, Oct 30, 2026•12 Day Trip
$1,089 USD
Returning
Sat, Oct 31, 2026•13 Day Trip
$1,129 USD
Returning
Sun, Nov 1, 2026•14 Day Trip
$1,288 USD