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: 22 Jul 2026
From
$194
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 10 Jul 2026
From
$147
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 31 Jul 2026
From
$162
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 03 Jun 2026
From
$198
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 06 Jun 2026
From
$133
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 31 May 2026
From
$241
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 18 Jun 2026
From
$129
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 30 Jun 2026
From
$229
Seen: 1 day ago
One-way
Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 03 May 2026
From
$184
Seen: 1 day ago
One-way
The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Depart: 18 May 2026
From
$85
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 21 Jul 2026
From
$152
Seen: 17 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 06 Jun 2026
From
$141
Seen: 13 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 | 06 Jun 2026 - 11 Jun 2026 | From $327 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 08 May 2026 - 10 May 2026 | From $327 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 09 Jul 2026 - 14 Jul 2026 | From $232 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 |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Jun 2026 - 07 Jun 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 05 Aug 2026 - 19 Aug 2026 | From $438 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 01 Feb 2027 - 06 Feb 2027 | From $244 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 08 Aug 2026 - 21 Aug 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 06 Aug 2026 - 11 Aug 2026 | From $232 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 08 Sep 2026 - 08 Sep 2026 | From $242 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 13 Oct 2026 - 13 Oct 2026 | From $242 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Jul 2026 - 02 Aug 2026 | From $407 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Jul 2026 - 15 Jul 2026 | From $407 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 20 Jan 2027 - 25 Jan 2027 | From $274 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 06 Nov 2026 - 08 Nov 2026 | From $274 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 27 Aug 2026 - 29 Aug 2026 | From $438 Seen: 20 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 10 Oct 2026 - 16 Oct 2026 | From $438 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 27 May 2026 - 13 Jun 2026 | From $421 Seen: 20 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 11 Nov 2026 - 14 Nov 2026 | From $244 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 31 Aug 2026 - 06 Sep 2026 | From $438 Seen: 8 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)06 Jun 2026 - 11 Jun 2026From$327Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)08 May 2026 - 10 May 2026From$327Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)09 Jul 2026 - 14 Jul 2026From$232Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)31 May 2026 - 06 Jun 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)03 Jun 2026 - 07 Jun 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)05 Aug 2026 - 19 Aug 2026From$438Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)01 Feb 2027 - 06 Feb 2027From$244Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)08 Aug 2026 - 21 Aug 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)06 Aug 2026 - 11 Aug 2026From$232Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)08 Sep 2026 - 08 Sep 2026From$242Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)13 Oct 2026 - 13 Oct 2026From$242Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)30 Jul 2026 - 02 Aug 2026From$407Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)12 Jul 2026 - 15 Jul 2026From$407Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)20 Jan 2027 - 25 Jan 2027From$274Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)06 Nov 2026 - 08 Nov 2026From$274Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)27 Aug 2026 - 29 Aug 2026From$438Seen: 20 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)10 Oct 2026 - 16 Oct 2026From$438Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)27 May 2026 - 13 Jun 2026From$421Seen: 20 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)11 Nov 2026 - 14 Nov 2026From$244Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)31 Aug 2026 - 06 Sep 2026From$438Seen: 8 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
