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: 11 Jun 2026
From
$194
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 22 Jun 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 06 Jun 2026
From
$229
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 19 May 2026
From
$162
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 24 Jun 2026
From
$241
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 29 May 2026
From
$192
Seen: 1 day ago
One-way
Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 18 May 2026
From
$184
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 19 Jun 2026
From
$129
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 10 Jun 2026
From
$199
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 15 Jul 2026
From
$254
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Jul 2026
From
$198
Seen: 59 minutes ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Jul 2026
From
$133
Seen: 15 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 | 09 Jul 2026 - 09 Jul 2026 | From $327 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 22 Jun 2026 - 07 Oct 2026 | From $327 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 19 Jul 2026 - 25 Jul 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 09 Aug 2026 - 16 Aug 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 17 Oct 2026 - 27 Oct 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 05 Aug 2026 - 10 Aug 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 23 Dec 2026 - 02 Jan 2027 | From $438 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 06 Sep 2026 - 10 Sep 2026 | From $438 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 11 Aug 2026 - 18 Aug 2026 | From $264 Seen: 16 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 05 Sep 2026 - 05 Sep 2026 | From $294 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 21 Sep 2026 - 25 Sep 2026 | From $361 Seen: 23 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Jun 2026 - 06 Aug 2026 | From $421 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 28 Jun 2026 - 01 Jul 2026 | From $407 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 03 Aug 2026 - 10 Aug 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | 24 May 2026 - 29 May 2026 | From $429 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | 23 May 2026 - 29 May 2026 | From $429 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Oct 2026 - 15 Oct 2026 | From $362 Seen: 1 hour ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Dec 2026 - 28 Dec 2026 | From $438 Seen: 4 minutes ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 04 Jul 2026 - 08 Jul 2026 | From $407 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 May 2026 - 19 May 2026 | From $421 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)09 Jul 2026 - 09 Jul 2026From$327Seen: 8 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)22 Jun 2026 - 07 Oct 2026From$327Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)19 Jul 2026 - 25 Jul 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)09 Aug 2026 - 16 Aug 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)17 Oct 2026 - 27 Oct 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)05 Aug 2026 - 10 Aug 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)23 Dec 2026 - 02 Jan 2027From$438Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)06 Sep 2026 - 10 Sep 2026From$438Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)11 Aug 2026 - 18 Aug 2026From$264Seen: 16 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)05 Sep 2026 - 05 Sep 2026From$294Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)21 Sep 2026 - 25 Sep 2026From$361Seen: 23 hrs agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)22 Jun 2026 - 06 Aug 2026From$421Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)28 Jun 2026 - 01 Jul 2026From$407Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)03 Aug 2026 - 10 Aug 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)24 May 2026 - 29 May 2026From$429Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)23 May 2026 - 29 May 2026From$429Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)08 Oct 2026 - 15 Oct 2026From$362Seen: 1 hour agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)24 Dec 2026 - 28 Dec 2026From$438Seen: 4 minutes agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)04 Jul 2026 - 08 Jul 2026From$407Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)19 May 2026 - 19 May 2026From$421Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
