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

Return flights

05 May - 20 May	Spirit Airlines
16 May - 20 May	Spirit Airlines
04 May - 20 May	Spirit Airlines
03 May - 20 May	Spirit Airlines
05 May - 08 May	Spirit Airlines
04 May - 08 May	Spirit Airlines
27 May - 01 Jun	Spirit Airlines
03 May - 08 May	Spirit Airlines
01 May - 20 May	Spirit Airlines
05 May - 10 May	Spirit Airlines
04 May - 10 May	Spirit Airlines
16 May - 01 Jun	Spirit Airlines
27 May - 14 Jun	Spirit Airlines

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

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 May from 233€

Return flights