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: 16 Feb 2026
From
$162
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 14 Dec 2025
From
$65
Seen: 18 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 07 Mar 2026
From
$141
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 18 Feb 2026
From
$220
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 17 Dec 2025
From
$136
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 11 Jan 2026
From
$172
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 05 Feb 2026
From
$114
Seen: 5 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Feb 2026
From
$137
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Dec 2025
From
$146
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 10 Jan 2026
From
$168
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Dec 2025
From
$85
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 15 Dec 2025
From
$218
Seen: 1 day 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 | 05 Mar 2026 - 09 Mar 2026 | From $269 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 10 Feb 2026 - 15 Feb 2026 | From $218 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 07 Mar 2026 - 14 Mar 2026 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 09 Feb 2026 - 10 Feb 2026 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 09 Oct 2026 - 13 Oct 2026 | From $409 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 21 Apr 2026 - 27 Apr 2026 | From $409 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 18 Jan 2026 - 21 Jan 2026 | From $168 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 11 Dec 2025 - 11 Dec 2025 | From $216 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Dec 2025 - 21 Dec 2025 | From $390 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 18 Mar 2026 - 23 Mar 2026 | From $236 Seen: 19 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 19 Mar 2026 - 23 Mar 2026 | From $236 Seen: 21 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Dec 2025 - 21 Dec 2025 | From $390 Seen: 19 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 28 Apr 2026 - 03 May 2026 | From $314 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Nov 2026 - 30 Nov 2026 | From $314 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Feb 2026 - 01 Mar 2026 | From $397 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Feb 2026 - 02 Mar 2026 | From $397 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 28 Feb 2026 - 02 Mar 2026 | From $281 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Dec 2025 - 09 Dec 2025 | From $226 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Dec 2025 - 09 Dec 2025 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | 08 Dec 2025 - 13 Dec 2025 | From $415 Seen: 21 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)05 Mar 2026 - 09 Mar 2026From$269Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)10 Feb 2026 - 15 Feb 2026From$218Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)07 Mar 2026 - 14 Mar 2026From$226Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)09 Feb 2026 - 10 Feb 2026From$226Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)09 Oct 2026 - 13 Oct 2026From$409Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)21 Apr 2026 - 27 Apr 2026From$409Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)18 Jan 2026 - 21 Jan 2026From$168Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)11 Dec 2025 - 11 Dec 2025From$216Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)21 Dec 2025 - 21 Dec 2025From$390Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)18 Mar 2026 - 23 Mar 2026From$236Seen: 19 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)19 Mar 2026 - 23 Mar 2026From$236Seen: 21 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)17 Dec 2025 - 21 Dec 2025From$390Seen: 19 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)28 Apr 2026 - 03 May 2026From$314Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)22 Nov 2026 - 30 Nov 2026From$314Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)25 Feb 2026 - 01 Mar 2026From$397Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)25 Feb 2026 - 02 Mar 2026From$397Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)28 Feb 2026 - 02 Mar 2026From$281Seen: 1 day agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)07 Dec 2025 - 09 Dec 2025From$226Seen: 1 day agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)08 Dec 2025 - 09 Dec 2025From$226Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)08 Dec 2025 - 13 Dec 2025From$415Seen: 21 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.