AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in January 2026 (see full year).
Return flights
| 18 Jan - 26 Jan | Southwest Airlines | ||
| 17 Jan - 24 Jan | Southwest Airlines | ||
| 27 Jan - 31 Jan | Delta | ||
| 10 Jan - 18 Jan | Delta | ||
| 01 Jan - 03 Jan | Delta |
Also check the deals for one-way flights from Chicago to San Juan in January.
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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