Cheapest return flights from Chicago to San Juan in December from $218

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

Return flights

07 Dec - 10 Dec Spirit Airlines direct
08 Dec - 13 Dec Spirit Airlines direct
07 Dec - 11 Dec Spirit Airlines direct
07 Dec - 08 Dec Spirit Airlines direct
07 Dec - 15 Dec Spirit Airlines direct
07 Dec - 16 Dec Spirit Airlines direct
07 Dec - 24 Dec Spirit Airlines direct
07 Dec - 13 Dec Spirit Airlines direct
07 Dec - 25 Dec Spirit Airlines direct
08 Dec - 11 Dec Spirit Airlines direct
11 Dec - 11 Jan Frontier Airlines
09 Dec - 12 Jan Spirit Airlines direct
31 Dec - 13 Jan Spirit Airlines direct
31 Dec - 07 Jan Spirit Airlines direct
31 Dec - 14 Jan Spirit Airlines direct
10 Dec - 12 Jan Spirit Airlines
31 Dec - 09 Jan Spirit Airlines
31 Dec - 08 Jan Spirit Airlines direct
31 Dec - 21 Jan Spirit Airlines
29 Dec - 13 Jan Spirit Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

Powered by

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.