Cheapest one-way flights from Chicago to San Juan in December from 184€

AirHint found the following cheapest one-way flights from Chicago (ORD) to San Juan (SJU) in December 2025 (see full year).

One-Way flights

15 Dec Southwest Airlines
16 Dec Southwest Airlines
16 Dec United direct
17 Dec Southwest Airlines
15 Dec United direct
18 Dec Southwest Airlines
17 Dec United direct
18 Dec United direct

Also check the deals for return flights from Chicago to San Juan in December.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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