Chicago (ORD) to San Juan (SJU) in October 2027

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CheapestLowHigherTypical $609

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October 2027from $609 · 4 trips

Chicago (ORD) to San Juan (SJU): what SlickTrip has seen

Cheapest economy round trip (6 nights) in October 2027: $609 leaving Fri, Oct 1, for 1 traveler.
16 price drops on economy fares in the last 30 days, caught for travelers watching this route. The typical drop was $40 a traveler (6.1%).
SlickTrip travelers are watching 8 trips on this route.
Airlines in the fares we watched: Frontier, United, American.

From SlickTrip's own price alerts and watched trips, as of Nov 10.

Chicago (ORD) to San Juan (SJU) by month

November 2026
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October 2027

Cheap economy Class Flights from Chicago (ORD) to San Juan (SJU) October

Find the best deals on economy class flights. Compare prices for direct flights, one-stop, and multi-stop options.

Chicago (ORD) to San Juan (SJU) in October 2027

Cheapest round trip of 4, 6, 9 nights fare in October 2027: $609 on 2027-10-01, for 1 traveler.

Why Choose Economy Class Flights from Chicago (ORD) to San Juan (SJU)?

Fares across the airlines on the route in one search
Nonstop and connecting flights side by side
A month of fares at a glance for october travel
Price alerts: we watch the fare and alert you when it drops

Planning a trip from Chicago (ORD) to San Juan (SJU) in october? SlickTrip shows the cheapest economy fares across airlines, nonstop or with stops. Set an alert and we watch the route for you, then email you when the price drops. Booking happens on the airline's or travel site's own page.

Chicago (ORD) to San Juan (SJU): what SlickTrip has seen

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