Find The Best Flight Deals from $55
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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
Willemstad, Curacao (CUR)Depart: 13 Dec 2026
From
$256
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 27 Oct 2026
From
$185
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 27 Oct 2026
From
$134
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 13 Dec 2026
From
$209
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Nov 2026
From
$213
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 14 Nov 2026
From
$179
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Oct 2026
From
$112
Seen: 20 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 17 Oct 2026
From
$59
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 21 Nov 2026
From
$122
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 10 Nov 2026
From
$172
Seen: 5 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)Depart: 27 Oct 2026
From
$197
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 15 Nov 2026
From
$369
Seen: 5 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) | Willemstad, Curacao (CUR) | Round-trip | 10 Nov 2026 - 19 Nov 2026 | From $468 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 27 Nov 2026 - 29 Nov 2026 | From $449 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 15 Oct 2026 - 15 Oct 2026 | From $206 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 28 Dec 2026 - 07 Jan 2027 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 01 Dec 2026 - 31 Dec 2026 | From $468 Seen: 10 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 05 Oct 2026 - 05 Oct 2026 | From $206 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 13 Nov 2026 - 18 Nov 2026 | From $291 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 29 Apr 2027 - 05 May 2027 | From $298 Seen: 17 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 14 Apr 2027 - 20 Apr 2027 | From $298 Seen: 17 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Apr 2027 - 11 Apr 2027 | From $294 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Dec 2026 - 25 Dec 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 26 Nov 2026 - 27 Nov 2026 | From $172 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 11 Dec 2026 - 12 Jan 2027 | From $674 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 01 Nov 2026 - 30 Nov 2026 | From $674 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 19 Dec 2026 - 29 Dec 2026 | From $381 Seen: 20 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Dec 2026 - 13 Dec 2026 | From $468 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 25 Oct 2026 - 01 Nov 2026 | From $172 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 25 Dec 2026 - 01 Jan 2027 | From $291 Seen: 5 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Nov 2026 - 22 Nov 2026 | From $468 Seen: 6 hrs ago |
| Oranjestad, Aruba (AUA) | Philipsburg, Sint Maarten (SXM) | Round-trip | 23 Nov 2026 - 23 Nov 2026 | From $674 Seen: 16 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
Willemstad, Curacao (CUR)10 Nov 2026 - 19 Nov 2026From$468Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)27 Nov 2026 - 29 Nov 2026From$449Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)15 Oct 2026 - 15 Oct 2026From$206Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)28 Dec 2026 - 07 Jan 2027From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)01 Dec 2026 - 31 Dec 2026From$468Seen: 10 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)05 Oct 2026 - 05 Oct 2026From$206Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)13 Nov 2026 - 18 Nov 2026From$291Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)29 Apr 2027 - 05 May 2027From$298Seen: 17 hrs agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)14 Apr 2027 - 20 Apr 2027From$298Seen: 17 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)09 Apr 2027 - 11 Apr 2027From$294Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)11 Dec 2026 - 25 Dec 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)26 Nov 2026 - 27 Nov 2026From$172Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)11 Dec 2026 - 12 Jan 2027From$674Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)01 Nov 2026 - 30 Nov 2026From$674Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)19 Dec 2026 - 29 Dec 2026From$381Seen: 20 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)11 Dec 2026 - 13 Dec 2026From$468Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)25 Oct 2026 - 01 Nov 2026From$172Seen: 8 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)25 Dec 2026 - 01 Jan 2027From$291Seen: 5 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)11 Nov 2026 - 22 Nov 2026From$468Seen: 6 hrs agoRound-tripOranjestad, Aruba (AUA)to
Philipsburg, Sint Maarten (SXM)23 Nov 2026 - 23 Nov 2026From$674Seen: 16 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.