AirHint found the following cheapest return flights from Chicago (MDW) to Havana (HAV) in December 2025 (see full year).
Return flights
| 21 Dec - 24 Dec | Southwest Airlines | ||
| 28 Dec - 06 Jan | Southwest Airlines | ||
| 27 Dec - 06 Jan | Southwest Airlines | ||
| 28 Dec - 05 Jan | Southwest Airlines | ||
| 27 Dec - 05 Jan | Southwest Airlines |
Also check the deals for one-way flights from Chicago to Havana in December.
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