Find The Best Flight Deals from $63
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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: 01 Jul 2026
From
$124
Seen: 12 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 22 Jul 2026
From
$241
Seen: 6 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 05 Sep 2026
From
$141
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Jun 2026
From
$112
Seen: 11 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 04 Aug 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 17 Jun 2026
From
$152
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 27 Jun 2026
From
$164
Seen: 3 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Jun 2026
From
$175
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)Depart: 20 Jun 2026
From
$154
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 22 Jun 2026
From
$63
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 03 Sep 2026
From
$124
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Sep 2026
From
$198
Seen: 1 day 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 | 18 Jun 2026 - 21 Jun 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 27 Jun 2026 - 29 Jun 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 12 Sep 2026 - 26 Sep 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 22 Nov 2026 - 28 Nov 2026 | From $438 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 26 Nov 2026 - 29 Nov 2026 | From $274 Seen: 3 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 05 Oct 2026 - 07 Oct 2026 | From $279 Seen: 5 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 30 Aug 2026 | From $311 Seen: 11 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 10 Jul 2026 | From $336 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 11 Jul 2026 - 12 Jul 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 14 Sep 2026 - 14 Sep 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 29 Jun 2026 - 30 Jun 2026 | From $242 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 23 Jul 2026 - 25 Jul 2026 | From $242 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 20 Jun 2026 - 20 Jun 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 07 Jul 2026 - 14 Jul 2026 | From $361 Seen: 22 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Jul 2026 - 18 Jul 2026 | From $429 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 02 Jul 2026 | From $429 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Bridgetown, Barbados (BGI) | Round-trip | 10 Sep 2026 - 17 Sep 2026 | From $330 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Bridgetown, Barbados (BGI) | Round-trip | 29 Aug 2026 - 29 Aug 2026 | From $330 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Jun 2026 - 27 Jun 2026 | From $186 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 29 Jun 2026 - 30 Jun 2026 | From $186 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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Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)18 Jun 2026 - 21 Jun 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)27 Jun 2026 - 29 Jun 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)12 Sep 2026 - 26 Sep 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)22 Nov 2026 - 28 Nov 2026From$438Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)26 Nov 2026 - 29 Nov 2026From$274Seen: 3 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)05 Oct 2026 - 07 Oct 2026From$279Seen: 5 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 30 Aug 2026From$311Seen: 11 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 10 Jul 2026From$336Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)11 Jul 2026 - 12 Jul 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)14 Sep 2026 - 14 Sep 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)29 Jun 2026 - 30 Jun 2026From$242Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)23 Jul 2026 - 25 Jul 2026From$242Seen: 8 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)20 Jun 2026 - 20 Jun 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)07 Jul 2026 - 14 Jul 2026From$361Seen: 22 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)12 Jul 2026 - 18 Jul 2026From$429Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 02 Jul 2026From$429Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)10 Sep 2026 - 17 Sep 2026From$330Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)29 Aug 2026 - 29 Aug 2026From$330Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)26 Jun 2026 - 27 Jun 2026From$186Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)29 Jun 2026 - 30 Jun 2026From$186Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
