Find The Best Flight Deals from $50
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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: 16 Aug 2026
From
$124
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 13 Aug 2026
From
$117
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 18 Aug 2026
From
$112
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 10 Sep 2026
From
$136
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Aug 2026
From
$162
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 09 Sep 2026
From
$241
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 09 Sep 2026
From
$198
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 27 Aug 2026
From
$192
Seen: 4 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 12 Sep 2026
From
$229
Seen: 5 hrs ago
One-way
Castries, Saint Lucia (SLU)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Jul 2026
From
$280
Seen: 1 hour ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 15 Aug 2026
From
$62
Seen: 18 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 13 Jul 2026
From
$224
Seen: 1 hour 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 | 27 Jul 2026 - 31 Jul 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 24 Jul 2026 - 30 Jul 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 15 Sep 2026 - 17 Sep 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 23 Sep 2026 - 23 Sep 2026 | From $172 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Dec 2026 - 13 Dec 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 28 Jul 2026 - 30 Jul 2026 | From $162 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 07 Aug 2026 - 09 Aug 2026 | From $162 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 04 Jun 2027 - 09 Jun 2027 | From $274 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 07 Jun 2027 - 10 Jun 2027 | From $274 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 18 Jul 2026 - 20 Jul 2026 | From $314 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 18 Oct 2026 - 01 Nov 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 24 Aug 2026 - 31 Aug 2026 | From $421 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Nov 2026 - 07 Dec 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 16 Sep 2026 - 21 Sep 2026 | From $474 Seen: 17 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Oct 2026 - 29 Oct 2026 | From $421 Seen: 16 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Aug 2026 - 15 Aug 2026 | From $361 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Dec 2026 - 26 Dec 2026 | From $421 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Aug 2026 - 12 Aug 2026 | From $186 Seen: 1 day ago |
| Castries, Saint Lucia (SLU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 14 Dec 2026 - 19 Dec 2026 | From $579 Seen: 20 hrs ago |
| Castries, Saint Lucia (SLU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Apr 2027 - 21 Apr 2027 | From $587 Seen: 18 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)27 Jul 2026 - 31 Jul 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)24 Jul 2026 - 30 Jul 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)15 Sep 2026 - 17 Sep 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)23 Sep 2026 - 23 Sep 2026From$172Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)11 Dec 2026 - 13 Dec 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)28 Jul 2026 - 30 Jul 2026From$162Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)07 Aug 2026 - 09 Aug 2026From$162Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)04 Jun 2027 - 09 Jun 2027From$274Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)07 Jun 2027 - 10 Jun 2027From$274Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)18 Jul 2026 - 20 Jul 2026From$314Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)18 Oct 2026 - 01 Nov 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)24 Aug 2026 - 31 Aug 2026From$421Seen: 22 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)30 Nov 2026 - 07 Dec 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)16 Sep 2026 - 21 Sep 2026From$474Seen: 17 hrs agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)22 Oct 2026 - 29 Oct 2026From$421Seen: 16 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)11 Aug 2026 - 15 Aug 2026From$361Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)19 Dec 2026 - 26 Dec 2026From$421Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)07 Aug 2026 - 12 Aug 2026From$186Seen: 1 day agoRound-tripCastries, Saint Lucia (SLU)to
Philipsburg, Sint Maarten (SXM)14 Dec 2026 - 19 Dec 2026From$579Seen: 20 hrs agoRound-tripCastries, Saint Lucia (SLU)to
Philipsburg, Sint Maarten (SXM)07 Apr 2027 - 21 Apr 2027From$587Seen: 18 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.