Cheapest one-way flights from Chicago to San Juan in December from $129

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

One-Way flights

04 Dec Spirit Airlines direct
05 Dec Spirit Airlines direct
03 Dec Spirit Airlines direct
06 Dec Spirit Airlines direct
11 Dec Frontier Airlines
15 Dec Spirit Airlines direct
02 Dec Spirit Airlines
11 Dec United direct
17 Dec Spirit Airlines direct
02 Dec Spirit 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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