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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Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 24 Mar 2026
From
$169
Seen: 1 day ago
One-way
Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 09 Feb 2026
From
$169
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)Depart: 19 Apr 2026
From
$208
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 14 Apr 2026
From
$152
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 10 Mar 2026
From
$108
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 11 Feb 2026
From
$183
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 14 Feb 2026
From
$107
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 23 Apr 2026
From
$226
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 28 Apr 2026
From
$165
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 14 Feb 2026
From
$110
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 10 Apr 2026
From
$219
Seen: 1 day ago
One-way
Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Depart: 23 Apr 2026
From
$97
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 |
|---|---|---|---|---|
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Apr 2026 - 06 Apr 2026 | From $377 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 May 2026 - 26 May 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: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 18 Feb 2026 - 04 Mar 2026 | From $194 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Port-of-Spain (POS) | Round-trip | 01 Apr 2026 - 15 Apr 2026 | From $377 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Port-of-Spain (POS) | Round-trip | 25 Oct 2026 - 28 Oct 2026 | From $377 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 10 Feb 2026 - 14 Feb 2026 | From $152 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 12 Mar 2026 - 17 Mar 2026 | From $614 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 23 Jun 2026 - 28 Jun 2026 | From $614 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 06 Apr 2026 - 10 Apr 2026 | From $409 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Feb 2026 - 11 Feb 2026 | From $277 Seen: 5 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 May 2026 - 12 May 2026 | From $277 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 11 Mar 2026 - 12 Mar 2026 | From $152 Seen: 5 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Aug 2026 - 15 Aug 2026 | From $408 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 Apr 2026 - 22 Apr 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 31 Aug 2026 - 10 Sep 2026 | From $408 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 08 Jul 2026 - 05 Aug 2026 | From $408 Seen: 21 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Apr 2026 - 04 May 2026 | From $341 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Jul 2026 - 09 Jul 2026 | From $341 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 Apr 2026 - 19 Apr 2026 | From $409 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)03 Apr 2026 - 06 Apr 2026From$377Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)22 May 2026 - 26 May 2026From$377Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)16 Feb 2026 - 16 Feb 2026From$184Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)18 Feb 2026 - 04 Mar 2026From$194Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)01 Apr 2026 - 15 Apr 2026From$377Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Port-of-Spain (POS)25 Oct 2026 - 28 Oct 2026From$377Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)10 Feb 2026 - 14 Feb 2026From$152Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)12 Mar 2026 - 17 Mar 2026From$614Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)23 Jun 2026 - 28 Jun 2026From$614Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)06 Apr 2026 - 10 Apr 2026From$409Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)11 Feb 2026 - 11 Feb 2026From$277Seen: 5 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)07 May 2026 - 12 May 2026From$277Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)11 Mar 2026 - 12 Mar 2026From$152Seen: 5 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)08 Aug 2026 - 15 Aug 2026From$408Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)15 Apr 2026 - 22 Apr 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)31 Aug 2026 - 10 Sep 2026From$408Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)08 Jul 2026 - 05 Aug 2026From$408Seen: 21 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)30 Apr 2026 - 04 May 2026From$341Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)03 Jul 2026 - 09 Jul 2026From$341Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)16 Apr 2026 - 19 Apr 2026From$409Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
