Cheapest one-way flights from Chicago to Philipsburg in May from $387

Best time to book flights for Chicago (MDW) to Philipsburg (SXM) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to Philipsburg (SXM) in May 2025 (see full year).

One-Way flights

21 May Volaris

Also check the deals for return flights from Chicago to Philipsburg in May.

Skyscanner

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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