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Cheapest return flights from Chicago (MDW) to Philipsburg (SXM), September

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Dates, airline, and price
Dates	Airline	Price
05 Sep 12 Sep	Southwest Airlines
20 Sep 24 Sep	Southwest Airlines
21 Sep 24 Sep	Southwest Airlines
23 Sep 24 Sep	Delta
22 Sep 24 Sep	Delta

deals for one-way flights from Chicago to Philipsburg in September.

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Updated Jul 4, 2026.

About these fares

These results come from our latest search across airlines for your currency. Prices change quickly and are not locked until you complete booking—always confirm the total and fare rules on the partner site.

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Cheapest return flights from Chicago (MDW) to Philipsburg (SXM), September

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