Cheapest return flights from Chicago to Philipsburg in December from $354

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

Return flights

31 Dec - 09 Jan Spirit Airlines
31 Dec - 07 Jan Spirit Airlines
31 Dec - 08 Jan Spirit Airlines
31 Dec - 10 Jan Spirit Airlines
28 Dec - 11 Jan Sun Country Airlines
25 Dec - 28 Dec Spirit Airlines
31 Dec - 05 Jan Spirit Airlines
31 Dec - 06 Jan Spirit Airlines
25 Dec - 01 Jan Spirit Airlines
28 Dec - 05 Jan Sun Country Airlines
27 Dec - 04 Jan Key Lime Air dba Denver Air Connection
23 Dec - 30 Dec jetBlue

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

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