Cheapest return flights from Chicago to San Juan in December from $256

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

Return flights

03 Dec - 09 Dec Spirit Airlines direct
04 Dec - 08 Dec Spirit Airlines direct
04 Dec - 12 Dec Spirit Airlines direct
04 Dec - 06 Dec Spirit Airlines direct
04 Dec - 09 Dec Spirit Airlines direct
05 Dec - 12 Dec Spirit Airlines direct
05 Dec - 06 Dec Spirit Airlines direct
09 Dec - 12 Dec Spirit Airlines direct
03 Dec - 12 Dec Spirit Airlines direct
03 Dec - 06 Dec Spirit Airlines direct
05 Dec - 09 Jan Spirit Airlines
30 Dec - 20 Jan Spirit Airlines direct
30 Dec - 17 Jan Spirit Airlines direct
31 Dec - 21 Jan Spirit Airlines direct
31 Dec - 30 Jan United
30 Dec - 13 Jan Spirit Airlines direct
31 Dec - 30 Jan Spirit Airlines direct
29 Dec - 17 Jan Spirit Airlines direct
31 Dec - 20 Jan Spirit Airlines direct
31 Dec - 17 Jan Spirit Airlines direct

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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