Cheapest return flights from Chicago to Philipsburg in May from $352

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

AirHint found the following cheapest return flights from Chicago (ORD) to Philipsburg (SXM) in May 2025 (see full year).

Return flights

12 May - 19 May Spirit Airlines
03 May - 09 May Spirit Airlines
08 May - 12 May Spirit Airlines
30 May - 07 Jun Frontier Airlines
31 May - 07 Jun Spirit Airlines
23 May - 30 May Frontier Airlines
19 May - 26 May Spirit Airlines
18 May - 25 May Spirit Airlines

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

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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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