AirHint found the following cheapest return flights from Chicago (ORD) to Philipsburg (SXM) in May 2026 (see full year).
Return flights
| 13 May - 16 May | Air Canada | ||
| 30 May - 06 Jun | Delta | ||
| 21 May - 26 May | Volaris | ||
| 27 May - 01 Jun | Delta | ||
| 23 May - 27 May | Frontier Airlines | ||
| 12 May - 19 May | Southwest Airlines | ||
| 17 May - 21 May | Viva |
Also check the deals for one-way flights from Chicago to Philipsburg in May.
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