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: 26 Mar 2026
From
$169
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 16 Mar 2026
From
$108
Seen: 1 hour ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 17 Feb 2026
From
$107
Seen: 5 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Apr 2026
From
$165
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 14 Mar 2026
From
$110
Seen: 8 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Apr 2026
From
$152
Seen: 1 day ago
One-way
Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Mar 2026
From
$169
Seen: 15 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 17 Mar 2026
From
$189
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 22 Feb 2026
From
$48
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 22 Apr 2026
From
$226
Seen: 21 hrs ago
One-way
The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Depart: 12 Mar 2026
From
$45
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 26 Feb 2026
From
$219
Seen: 16 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 | 05 Mar 2026 - 05 Mar 2026 | From $277 Seen: 17 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 26 Mar 2026 - 26 Mar 2026 | From $277 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 18 Feb 2026 - 19 Feb 2026 | From $277 Seen: 10 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Mar 2026 - 11 Apr 2026 | From $277 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 24 Feb 2026 - 26 Feb 2026 | From $195 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 03 Mar 2026 - 05 Mar 2026 | From $152 Seen: 10 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 09 Mar 2026 - 11 Mar 2026 | From $152 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 Mar 2026 - 25 Mar 2026 | From $409 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Feb 2026 - 17 Feb 2026 | From $409 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 03 Mar 2026 - 04 Mar 2026 | From $195 Seen: 19 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 May 2026 - 31 May 2026 | From $341 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Oct 2026 - 24 Oct 2026 | From $341 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Mar 2026 - 23 Mar 2026 | From $377 Seen: 1 day ago |
| Port-of-Spain (POS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 29 Apr 2026 - 06 May 2026 | From $377 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 10 Jul 2026 - 13 Jul 2026 | From $401 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 28 Jun 2026 - 05 Jul 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 13 May 2026 - 18 May 2026 | From $408 Seen: 16 hrs ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Feb 2026 - 25 Feb 2026 | From $197 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 23 Mar 2026 - 26 Mar 2026 | From $222 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Jul 2026 - 27 Jul 2026 | From $408 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)05 Mar 2026 - 05 Mar 2026From$277Seen: 17 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)26 Mar 2026 - 26 Mar 2026From$277Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)18 Feb 2026 - 19 Feb 2026From$277Seen: 10 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)30 Mar 2026 - 11 Apr 2026From$277Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)24 Feb 2026 - 26 Feb 2026From$195Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)03 Mar 2026 - 05 Mar 2026From$152Seen: 10 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)09 Mar 2026 - 11 Mar 2026From$152Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)15 Mar 2026 - 25 Mar 2026From$409Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)17 Feb 2026 - 17 Feb 2026From$409Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)03 Mar 2026 - 04 Mar 2026From$195Seen: 19 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 May 2026 - 31 May 2026From$341Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)19 Oct 2026 - 24 Oct 2026From$341Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)19 Mar 2026 - 23 Mar 2026From$377Seen: 1 day agoRound-tripPort-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)29 Apr 2026 - 06 May 2026From$377Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)10 Jul 2026 - 13 Jul 2026From$401Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)28 Jun 2026 - 05 Jul 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)13 May 2026 - 18 May 2026From$408Seen: 16 hrs agoRound-tripThe Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)24 Feb 2026 - 25 Feb 2026From$197Seen: 1 day agoRound-tripThe Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)23 Mar 2026 - 26 Mar 2026From$222Seen: 18 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)17 Jul 2026 - 27 Jul 2026From$408Seen: 18 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.