Find The Best Flight Deals from $65
Travel Throughout the Caribbean with Winair, with these best one way flight deals

Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.
Popular Flight Deals with Winair
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 10 Feb 2026 - 15 Feb 2026 | From $218 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 11 Jan 2026 - 18 Jan 2026 | From $218 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 13 Jun 2026 - 20 Jun 2026 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 09 Dec 2025 - 10 Dec 2025 | From $226 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 05 May 2026 - 05 May 2026 | From $231 Seen: 46 minutes ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 May 2026 - 17 May 2026 | From $390 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 09 Jan 2026 - 09 Jan 2026 | From $216 Seen: 11 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 22 Aug 2026 - 27 Aug 2026 | From $231 Seen: 11 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 17 Dec 2025 - 18 Dec 2025 | From $216 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Dec 2025 - 14 Dec 2025 | From $390 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Dec 2025 - 28 Dec 2025 | From $226 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Apr 2026 - 08 Apr 2026 | From $314 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 May 2026 - 31 May 2026 | From $397 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Apr 2026 - 17 Apr 2026 | From $397 Seen: 14 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Apr 2026 - 20 Apr 2026 | From $226 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 07 Aug 2026 - 09 Aug 2026 | From $256 Seen: 16 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 06 Oct 2026 - 10 Oct 2026 | From $261 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Aug 2026 - 30 Aug 2026 | From $314 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 16 Apr 2026 - 17 Apr 2026 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 06 Apr 2026 - 07 Apr 2026 | From $314 Seen: 17 hrs ago |
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply.
Most Popular Round trip Flight Deals with Winair
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.


