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

Return flights

15 Jan - 21 Jan	Copa
02 Jan - 17 Jan	Spirit Airlines
02 Jan - 09 Jan	Spirit Airlines
02 Jan - 10 Jan	Spirit Airlines
15 Jan - 24 Feb	Air Canada
24 Jan - 31 Jan	United	direct
02 Jan - 03 Jan	Spirit 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 412€

Return flights