Find The Best Flight Deals from $45
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Travel Throughout the Caribbean with Winair, with these best one way flight deals
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Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Mar 2026
From
$169
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 04 Mar 2026
From
$169
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Feb 2026
From
$152
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)Depart: 28 Mar 2026
From
$208
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 30 Mar 2026
From
$189
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Mar 2026
From
$165
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 15 Apr 2026
From
$226
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Mar 2026
From
$183
Seen: 23 hrs ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 23 Feb 2026
From
$108
Seen: 5 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 26 Mar 2026
From
$339
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Philipsburg, Sint Maarten (SXM)Depart: 05 Mar 2026
From
$276
Seen: 5 hrs ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 07 Mar 2026
From
$147
Seen: 9 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 |
|---|---|---|---|---|
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Nov 2026 - 25 Nov 2026 | From $377 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Jul 2026 - 10 Jul 2026 | From $377 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 16 Feb 2026 - 16 Feb 2026 | From $184 Seen: 58 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 18 Feb 2026 - 04 Mar 2026 | From $194 Seen: 34 minutes ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 18 Feb 2026 - 28 Feb 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 30 Apr 2026 - 09 May 2026 | From $614 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 13 Apr 2026 - 20 Apr 2026 | From $408 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Mar 2026 - 07 Jun 2026 | From $366 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Port-of-Spain (POS) | Round-trip | 07 Feb 2026 - 11 Feb 2026 | From $377 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Port-of-Spain (POS) | Round-trip | 08 Jul 2026 - 20 Jul 2026 | From $377 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 07 Feb 2026 - 07 Feb 2026 | From $341 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Apr 2026 - 02 May 2026 | From $341 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 26 Mar 2026 - 30 Mar 2026 | From $408 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 24 Jun 2026 - 28 Jun 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 10 Feb 2026 - 14 Feb 2026 | From $152 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 23 Jun 2026 - 28 Jun 2026 | From $614 Seen: 18 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Feb 2026 - 09 Feb 2026 | From $409 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 27 Aug 2026 - 31 Aug 2026 | From $409 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 14 Feb 2026 - 21 Feb 2026 | From $187 Seen: 4 hrs ago |
| Charlestown, Nevis (NEV) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Sep 2026 - 05 Sep 2026 | From $339 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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Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)25 Nov 2026 - 25 Nov 2026From$377Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)05 Jul 2026 - 10 Jul 2026From$377Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)16 Feb 2026 - 16 Feb 2026From$184Seen: 58 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)18 Feb 2026 - 04 Mar 2026From$194Seen: 34 minutes agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)18 Feb 2026 - 28 Feb 2026From$341Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)30 Apr 2026 - 09 May 2026From$614Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)13 Apr 2026 - 20 Apr 2026From$408Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)13 Mar 2026 - 07 Jun 2026From$366Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)07 Feb 2026 - 11 Feb 2026From$377Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)08 Jul 2026 - 20 Jul 2026From$377Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)07 Feb 2026 - 07 Feb 2026From$341Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Apr 2026 - 02 May 2026From$341Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)26 Mar 2026 - 30 Mar 2026From$408Seen: 16 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)24 Jun 2026 - 28 Jun 2026From$341Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)10 Feb 2026 - 14 Feb 2026From$152Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)23 Jun 2026 - 28 Jun 2026From$614Seen: 18 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)07 Feb 2026 - 09 Feb 2026From$409Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)27 Aug 2026 - 31 Aug 2026From$409Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)14 Feb 2026 - 21 Feb 2026From$187Seen: 4 hrs agoRound-tripCharlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)01 Sep 2026 - 05 Sep 2026From$339Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
