Find The Best Flight Deals from $85
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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: 30 Jul 2026
From
$194
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 30 May 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 02 Jun 2026
From
$229
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Aug 2026
From
$198
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 03 Jun 2026
From
$199
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Jul 2026
From
$162
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Kingstown, Saint Vincent (SVD)Depart: 28 May 2026
From
$294
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 05 Aug 2026
From
$241
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 06 Jun 2026
From
$141
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Jul 2026
From
$175
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 14 May 2026
From
$133
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 27 Jul 2026
From
$124
Seen: 12 hrs 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 | 20 Jun 2026 - 27 Jun 2026 | From $327 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 15 May 2026 - 17 May 2026 | From $327 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Jul 2026 - 13 Aug 2026 | From $438 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 14 Sep 2026 - 20 Sep 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 06 Jun 2026 - 16 Jun 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 30 Jun 2026 - 05 Jul 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 29 Nov 2026 - 10 Jan 2027 | From $438 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 05 Aug 2026 - 09 Aug 2026 | From $438 Seen: 11 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 10 Nov 2026 - 17 Nov 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 06 Aug 2026 - 14 Aug 2026 | From $421 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 03 Jun 2026 - 03 Jun 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 21 May 2026 - 28 May 2026 | From $361 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 Aug 2026 - 30 Aug 2026 | From $361 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 31 May 2026 - 06 Jun 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Kingstown, Saint Vincent (SVD) | Round-trip | 15 Jun 2026 - 29 Jun 2026 | From $509 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Jul 2026 - 22 Jul 2026 | From $327 Seen: 23 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Aug 2026 - 26 Aug 2026 | From $327 Seen: 13 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 15 Jan 2027 - 20 Jan 2027 | From $274 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 02 Oct 2026 - 09 Oct 2026 | From $274 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 02 Jul 2026 - 06 Jul 2026 | From $429 Seen: 1 day 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)20 Jun 2026 - 27 Jun 2026From$327Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)15 May 2026 - 17 May 2026From$327Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)30 Jul 2026 - 13 Aug 2026From$438Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)14 Sep 2026 - 20 Sep 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)06 Jun 2026 - 16 Jun 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)30 Jun 2026 - 05 Jul 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)29 Nov 2026 - 10 Jan 2027From$438Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)05 Aug 2026 - 09 Aug 2026From$438Seen: 11 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)10 Nov 2026 - 17 Nov 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)06 Aug 2026 - 14 Aug 2026From$421Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)03 Jun 2026 - 03 Jun 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)21 May 2026 - 28 May 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)16 Aug 2026 - 30 Aug 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)31 May 2026 - 06 Jun 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Kingstown, Saint Vincent (SVD)15 Jun 2026 - 29 Jun 2026From$509Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)13 Jul 2026 - 22 Jul 2026From$327Seen: 23 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)08 Aug 2026 - 26 Aug 2026From$327Seen: 13 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)15 Jan 2027 - 20 Jan 2027From$274Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)02 Oct 2026 - 09 Oct 2026From$274Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)02 Jul 2026 - 06 Jul 2026From$429Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
