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: 26 Jul 2026
From
$194
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 29 Jul 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 07 Jun 2026
From
$241
Seen: 15 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Jul 2026
From
$198
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 24 Jun 2026
From
$229
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Jun 2026
From
$133
Seen: 2 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 27 Jun 2026
From
$112
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 27 Jun 2026
From
$164
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 24 Aug 2026
From
$141
Seen: 16 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 02 Jul 2026
From
$152
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Jul 2026
From
$192
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 03 Aug 2026
From
$129
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 | 14 Jan 2027 - 18 Jan 2027 | From $234 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 20 Jul 2026 - 20 Jul 2026 | From $279 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 30 Jul 2026 - 02 Aug 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 30 Jun 2026 - 30 Jun 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 25 Nov 2026 - 30 Nov 2026 | From $362 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 07 Nov 2026 - 14 Nov 2026 | From $438 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Nov 2026 - 25 Nov 2026 | From $234 Seen: 22 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Jul 2026 - 29 Jul 2026 | From $326 Seen: 17 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 25 Feb 2027 - 28 Feb 2027 | From $274 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 08 Sep 2026 - 19 Sep 2026 | From $421 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Jun 2026 - 29 Jun 2026 | From $311 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Jun 2026 - 30 Jun 2026 | From $311 Seen: 16 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 28 Jan 2027 - 02 Feb 2027 | From $274 Seen: 6 minutes ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Sep 2026 - 02 Oct 2026 | From $438 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Sep 2026 - 04 Oct 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 24 Jul 2026 - 27 Jul 2026 | From $242 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 20 Dec 2026 - 03 Jan 2027 | From $421 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 11 Jan 2027 - 20 Jan 2027 | From $244 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 13 Feb 2027 - 20 Feb 2027 | From $244 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Jun 2026 - 06 Jul 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)14 Jan 2027 - 18 Jan 2027From$234Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)20 Jul 2026 - 20 Jul 2026From$279Seen: 4 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)30 Jul 2026 - 02 Aug 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)30 Jun 2026 - 30 Jun 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)25 Nov 2026 - 30 Nov 2026From$362Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)07 Nov 2026 - 14 Nov 2026From$438Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)19 Nov 2026 - 25 Nov 2026From$234Seen: 22 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)17 Jul 2026 - 29 Jul 2026From$326Seen: 17 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)25 Feb 2027 - 28 Feb 2027From$274Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)08 Sep 2026 - 19 Sep 2026From$421Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Jun 2026 - 29 Jun 2026From$311Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Jun 2026 - 30 Jun 2026From$311Seen: 16 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)28 Jan 2027 - 02 Feb 2027From$274Seen: 6 minutes agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)13 Sep 2026 - 02 Oct 2026From$438Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)30 Sep 2026 - 04 Oct 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)24 Jul 2026 - 27 Jul 2026From$242Seen: 22 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)20 Dec 2026 - 03 Jan 2027From$421Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)11 Jan 2027 - 20 Jan 2027From$244Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)13 Feb 2027 - 20 Feb 2027From$244Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)05 Jun 2026 - 06 Jul 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.
