Cheapest return flights from Chicago to San Juan in December from $278

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

Return flights

08 Dec - 12 Dec Frontier Airlines
05 Dec - 07 Dec Frontier Airlines
14 Dec - 17 Dec Frontier Airlines
13 Dec - 16 Dec Frontier Airlines
06 Dec - 13 Dec Frontier Airlines
05 Dec - 13 Dec Frontier Airlines
05 Dec - 08 Dec Frontier Airlines
04 Dec - 09 Dec Frontier Airlines
15 Dec - 17 Dec Frontier Airlines
14 Dec - 20 Dec Southwest Airlines
30 Dec - 10 Jan Frontier Airlines
29 Dec - 06 Jan Frontier Airlines
31 Dec - 30 Jan Frontier Airlines
30 Dec - 06 Jan Frontier Airlines
24 Dec - 10 Jan Frontier Airlines
18 Dec - 10 Jan Frontier Airlines
18 Dec - 02 Jan Frontier Airlines
28 Dec - 04 Jan Frontier Airlines
21 Dec - 03 Jan Frontier Airlines
26 Dec - 02 Jan Frontier Airlines

Also check the deals for one-way 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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