Cheapest one-way flights from Chicago to San Juan in December from $101

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

One-Way flights

31 Dec Frontier Airlines
07 Dec Spirit Airlines direct
06 Dec Spirit Airlines
12 Dec Spirit Airlines direct
02 Dec Spirit Airlines
05 Dec Frontier Airlines
04 Dec Frontier Airlines
31 Dec Spirit Airlines direct
02 Dec Spirit Airlines direct
14 Dec Spirit Airlines direct

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

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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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