Cheapest one-way flights from Chicago to San Juan in December from 183€

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

One-Way flights

31 Dec Southwest Airlines
30 Dec Southwest Airlines
20 Dec Southwest Airlines
24 Dec Southwest Airlines
01 Dec Frontier Airlines
19 Dec Southwest 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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