Cheapest one-way flights from Chicago to San Juan in December from $139

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

One-Way flights

15 Dec Frontier Airlines
12 Dec Frontier Airlines
04 Dec Frontier Airlines
30 Dec Delta
23 Dec Frontier Airlines
20 Dec Frontier Airlines
28 Dec Frontier Airlines
26 Dec Frontier Airlines
20 Dec Southwest 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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