AirHint found the following cheapest return flights from Chicago (MDW) to Philipsburg (SXM) in December 2025 (see full year).
Return flights
| 15 Dec - 18 Dec | Delta | ||
| 07 Dec - 13 Dec | Frontier Airlines | ||
| 01 Dec - 03 Dec | Porter Airlines (Canada) Ltd | ||
| 27 Dec - 03 Jan | Frontier Airlines |
Also check the deals for one-way flights from Chicago to Philipsburg in December.
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