Cheapest return flights from Chicago to San Juan in December from 366€

Best time to book flights for Chicago (ORD) to San Juan (SJU) flights at AirHint

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

Return flights

03 Dec - 10 Dec American Airlines
14 Dec - 20 Dec United
17 Dec - 26 Dec United direct
24 Dec - 28 Dec Delta
23 Dec - 26 Dec Delta
20 Dec - 25 Dec Delta
18 Dec - 28 Dec Delta
20 Dec - 26 Dec Delta
20 Dec - 26 Dec United direct
23 Dec - 26 Dec United direct
27 Dec - 03 Jan United direct
20 Dec - 03 Jan United direct

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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