AirHint found the following cheapest return flights from Chicago (ORD) to Philipsburg (SXM) in January 2026 (see full year).

Return flights

29 Jan - 05 Feb	Spirit Airlines
28 Jan - 09 Feb	Spirit Airlines
02 Jan - 09 Jan	Spirit Airlines
02 Jan - 08 Jan	Spirit Airlines
03 Jan - 09 Jan	Spirit Airlines
03 Jan - 08 Jan	Spirit Airlines
03 Jan - 10 Jan	Spirit Airlines
02 Jan - 10 Jan	Spirit Airlines
03 Jan - 07 Jan	Spirit Airlines
16 Jan - 27 Jan	Spirit Airlines
27 Jan - 03 Feb	Spirit Airlines
27 Jan - 10 Feb	Spirit Airlines
02 Jan - 05 Jan	Spirit Airlines
14 Jan - 20 Jan	American Airlines

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

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Chicago to Philipsburg in January from $240

Return flights