Cheapest return flights from Chicago to San Juan in December from 343€

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

Return flights

04 Dec - 14 Dec United
06 Dec - 11 Dec Southwest Airlines
14 Dec - 21 Dec United
13 Dec - 21 Dec United
12 Dec - 19 Dec United direct
18 Dec - 10 Jan Southwest Airlines
25 Dec - 05 Jan Delta
24 Dec - 10 Jan Southwest Airlines
29 Dec - 02 Jan Southwest Airlines
27 Dec - 02 Jan Southwest Airlines
31 Dec - 04 Jan Southwest Airlines
25 Dec - 31 Dec Delta
29 Dec - 03 Jan Southwest Airlines
26 Dec - 30 Dec Sun Country Airlines
26 Dec - 01 Jan Southwest Airlines
24 Dec - 04 Jan Southwest Airlines
25 Dec - 02 Jan Southwest Airlines
26 Dec - 31 Dec Southwest Airlines

Also check the deals for one-way 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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