Cheapest return flights from Chicago to Philipsburg in December from $329

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
22 Dec - 09 Jan Spirit Airlines
22 Dec - 10 Jan Spirit Airlines
13 Dec - 20 Dec United direct
29 Dec - 09 Jan Spirit Airlines
29 Dec - 10 Jan Spirit Airlines
14 Dec - 19 Dec United
03 Dec - 08 Dec Frontier Airlines
06 Dec - 13 Dec Spirit Airlines
06 Dec - 15 Dec Spirit Airlines
21 Dec - 10 Jan Spirit Airlines
06 Dec - 20 Dec Spirit Airlines
20 Dec - 09 Jan Spirit Airlines
19 Dec - 21 Dec Spirit Airlines
28 Dec - 11 Jan Spirit Airlines
13 Dec - 02 Jan Spirit Airlines
22 Dec - 02 Jan Spirit Airlines
29 Dec - 02 Jan Spirit Airlines
26 Dec - 31 Dec Contour Airlines

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

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