Cheapest one-way flights from Chicago to San Juan in December from $271

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

One-Way flights

17 Dec jetBlue
16 Dec American Airlines direct
29 Dec Delta
28 Dec Sun Country Airlines
27 Dec Southwest Airlines
29 Dec United direct
26 Dec Air Canada
18 Dec Southwest Airlines
18 Dec American Airlines direct
17 Dec American Airlines 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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