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: 02 Jul 2026
From
$194
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 27 May 2026
From
$133
Seen: 22 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 04 Jul 2026
From
$147
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Jun 2026
From
$162
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 18 May 2026
From
$229
Seen: 17 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Aug 2026
From
$198
Seen: 23 hrs ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 30 Jun 2026
From
$129
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 21 Jul 2026
From
$152
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 12 Jun 2026
From
$199
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
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 16 May 2026
From
$254
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Aug 2026
From
$192
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 | 08 Jun 2026 - 08 Jun 2026 | From $327 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 07 Jun 2026 - 13 Jun 2026 | From $327 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 13 May 2026 - 18 May 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 10 Jun 2026 - 10 Jun 2026 | From $232 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jun 2026 - 23 Oct 2026 | From $327 Seen: 39 minutes ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Jun 2026 - 30 Jun 2026 | From $361 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jun 2026 - 30 Jun 2026 | From $361 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 10 Jul 2026 - 15 Jul 2026 | From $438 Seen: 1 hour ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Aug 2026 - 09 Aug 2026 | From $407 Seen: 13 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Nov 2026 - 28 Nov 2026 | From $438 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | 27 May 2026 - 18 Jun 2026 | From $429 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 30 Sep 2026 - 26 Oct 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 08 May 2026 - 14 May 2026 | From $421 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 May 2026 - 20 May 2026 | From $407 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 11 Nov 2026 - 14 Nov 2026 | From $244 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Jul 2026 - 26 Jul 2026 | From $421 Seen: 13 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 31 Aug 2026 - 06 Sep 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 03 Sep 2026 - 06 Sep 2026 | From $438 Seen: 20 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Jun 2026 - 17 Jun 2026 | From $327 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 22 Jan 2027 - 31 Jan 2027 | From $244 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)08 Jun 2026 - 08 Jun 2026From$327Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)07 Jun 2026 - 13 Jun 2026From$327Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)13 May 2026 - 18 May 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)10 Jun 2026 - 10 Jun 2026From$232Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)01 Jun 2026 - 23 Oct 2026From$327Seen: 39 minutes agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)09 Jun 2026 - 30 Jun 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)01 Jun 2026 - 30 Jun 2026From$361Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)10 Jul 2026 - 15 Jul 2026From$438Seen: 1 hour agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)05 Aug 2026 - 09 Aug 2026From$407Seen: 13 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)21 Nov 2026 - 28 Nov 2026From$438Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)27 May 2026 - 18 Jun 2026From$429Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)30 Sep 2026 - 26 Oct 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)08 May 2026 - 14 May 2026From$421Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)17 May 2026 - 20 May 2026From$407Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)11 Nov 2026 - 14 Nov 2026From$244Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)07 Jul 2026 - 26 Jul 2026From$421Seen: 13 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)31 Aug 2026 - 06 Sep 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)03 Sep 2026 - 06 Sep 2026From$438Seen: 20 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)08 Jun 2026 - 17 Jun 2026From$327Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)22 Jan 2027 - 31 Jan 2027From$244Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
