AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in January 2027 (see full year).
Return flights
| 06 Jan - 13 Jan | United | direct | |
| 03 Jan - 23 Jan | United | ||
| 03 Jan - 24 Jan | United | ||
| 22 Jan - 25 Jan | United | ||
| 31 Jan - 20 Feb | United | direct | |
| 31 Jan - 21 Feb | United | direct | |
| 03 Jan - 03 Jan | United |
Also check the deals for one-way flights from Chicago to San Juan in January.
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