Find The Best Flight Deals from $65
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Travel Throughout the Caribbean with Winair, with these best one way flight deals
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Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 01 Mar 2026
From
$162
Seen: 22 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 17 Dec 2025
From
$141
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Dec 2025
From
$65
Seen: 13 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 14 Feb 2026
From
$220
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 25 Feb 2026
From
$109
Seen: 16 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 23 Jan 2026
From
$136
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Dec 2025
From
$172
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 28 Jan 2026
From
$85
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 24 Jan 2026
From
$137
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 01 Jan 2026
From
$218
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 19 Jan 2026
From
$168
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Dec 2025
From
$146
Seen: 1 minute ago
One-way
*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
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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
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Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)10 Feb 2026 - 15 Feb 2026From$218Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)11 Jan 2026 - 18 Jan 2026From$218Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)13 Jun 2026 - 20 Jun 2026From$226Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)09 Dec 2025 - 10 Dec 2025From$226Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)05 May 2026 - 05 May 2026From$231Seen: 46 minutes agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)15 May 2026 - 17 May 2026From$390Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)09 Jan 2026 - 09 Jan 2026From$216Seen: 11 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)22 Aug 2026 - 27 Aug 2026From$231Seen: 11 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)17 Dec 2025 - 18 Dec 2025From$216Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)11 Dec 2025 - 14 Dec 2025From$390Seen: 1 day agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)25 Dec 2025 - 28 Dec 2025From$226Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)03 Apr 2026 - 08 Apr 2026From$314Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)24 May 2026 - 31 May 2026From$397Seen: 18 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)17 Apr 2026 - 17 Apr 2026From$397Seen: 14 hrs agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)17 Apr 2026 - 20 Apr 2026From$226Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)07 Aug 2026 - 09 Aug 2026From$256Seen: 16 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)06 Oct 2026 - 10 Oct 2026From$261Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)21 Aug 2026 - 30 Aug 2026From$314Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)16 Apr 2026 - 17 Apr 2026From$397Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)06 Apr 2026 - 07 Apr 2026From$314Seen: 17 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.