Flights from Chicago, IL to San Juan, PR

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Best Deals on Flights From Chicago, IL (ORD) to San Juan, PR (SJU)

Try alternate month or interact with individual days below in order to find offers.
Apr 2026
No results for this month.
May 2026
from$78*
Last seen: 21 hours ago
One-way/Economy
Jun 2026
from$98*
Last seen: 17 hours ago
One-way/Economy
$78
$200
Displaying fares for April-2026
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    • Range$78-$200

    *Prices found by others in the previous 48 hours for round-trip flights. Prices shown may also require membership in our travel club, Discount Den.

    Flights Deals from Chicago, IL to San Juan, PR on Frontier

    $
    Flights Deals from Chicago, IL to San Juan, PR on Frontier
    From
    To
    Chicago, IL (ORD)San Juan, PR (SJU)One-way
    /
    Discount Den Basic Fare    		Departing Sep 2, 2026

    From

    $48

    Last seen: 53 mins ago

    *Prices found by others in the previous 48 hours for one-way flights. Prices shown may also require membership in our travel club, Discount Den®.

    Chicago, IL San Juan, PR

    Barclays Badge

    Earn 50,000 Miles after qualifying activity. Plus $0 Intro Annual Fee, then $99.
    Terms Apply.