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

Return flights

06 Jan - 27 Jan	WestJet
06 Jan - 28 Jan	WestJet
06 Jan - 09 Jan	WestJet
07 Jan - 28 Jan	WestJet
07 Jan - 13 Jan	WestJet
07 Jan - 27 Jan	WestJet
07 Jan - 04 Feb	WestJet
13 Jan - 18 Jan	WestJet
14 Jan - 11 Feb	WestJet
07 Jan - 17 Jan	WestJet
13 Jan - 06 Feb	WestJet
16 Jan - 08 Feb	WestJet
14 Jan - 07 Feb	WestJet
01 Jan - 18 Jan	WestJet
04 Jan - 19 Jan	WestJet

Also check the deals for one-way flights from Winnipeg 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 Winnipeg to Philipsburg in January from 323€

Return flights