Cheapest return flights from Chicago to Philipsburg in December from $330

AirHint found the following cheapest return flights from Chicago (ORD) to Philipsburg (SXM) in December 2025 (see full year).

Return flights

13 Dec - 20 Dec Spirit Airlines
13 Dec - 15 Dec Spirit Airlines
13 Dec - 20 Dec United direct
29 Dec - 10 Jan Spirit Airlines
03 Dec - 08 Dec Frontier Airlines
06 Dec - 13 Dec Spirit Airlines
13 Dec - 27 Dec Spirit Airlines
06 Dec - 15 Dec Spirit Airlines
21 Dec - 10 Jan Spirit Airlines
06 Dec - 20 Dec Spirit Airlines
22 Dec - 30 Dec Spirit Airlines
21 Dec - 29 Dec Frontier Airlines
28 Dec - 11 Jan Frontier Airlines
13 Dec - 02 Jan Spirit Airlines
29 Dec - 02 Jan Spirit Airlines
20 Dec - 02 Jan Spirit Airlines
29 Dec - 03 Jan Spirit Airlines
28 Dec - 03 Jan Frontier Airlines
20 Dec - 03 Jan Spirit Airlines
21 Dec - 10 Jan United direct

Also check the deals for one-way flights from Chicago to Philipsburg in December.

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