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: 18 Aug 2026
From
$124
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 08 Jul 2026
From
$241
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 10 Sep 2026
From
$136
Seen: 1 hour ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 24 Jun 2026
From
$112
Seen: 20 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 08 Jul 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 15 Aug 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: 22 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 07 Aug 2026
From
$175
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)Depart: 08 Aug 2026
From
$154
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 27 Jun 2026
From
$63
Seen: 23 hrs ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 08 Jul 2026
From
$139
Seen: 2 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 10 Aug 2026
From
$198
Seen: 10 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 | 09 Jul 2026 - 10 Jul 2026 | From $94 Seen: 17 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 15 Jun 2026 - 18 Jun 2026 | From $186 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 01 Dec 2026 - 02 Dec 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 22 Nov 2026 - 13 Dec 2026 | From $438 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 20 Dec 2026 - 23 Dec 2026 | From $274 Seen: 23 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 10 Jan 2027 - 17 Jan 2027 | From $274 Seen: 4 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 27 Jun 2026 | From $311 Seen: 19 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 Jul 2026 - 31 Jul 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 11 Jul 2026 - 12 Jul 2026 | From $232 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 21 Oct 2026 - 23 Oct 2026 | From $232 Seen: 2 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 07 Oct 2026 - 10 Oct 2026 | From $242 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 19 Nov 2026 - 19 Nov 2026 | From $242 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 01 Dec 2026 - 01 Dec 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 02 Jul 2026 - 09 Aug 2026 | From $361 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 10 Oct 2026 - 15 Oct 2026 | From $429 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Aug 2026 - 03 Aug 2026 | From $429 Seen: 22 hrs ago |
| Basseterre, Saint Kitts (SKB) | Bridgetown, Barbados (BGI) | Round-trip | 31 Jul 2026 - 09 Aug 2026 | From $330 Seen: 16 hrs ago |
| Basseterre, Saint Kitts (SKB) | Bridgetown, Barbados (BGI) | Round-trip | 25 Jun 2026 - 03 Jul 2026 | From $375 Seen: 20 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Jun 2026 - 27 Jun 2026 | From $186 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 25 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)09 Jul 2026 - 10 Jul 2026From$94Seen: 17 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)15 Jun 2026 - 18 Jun 2026From$186Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)01 Dec 2026 - 02 Dec 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)22 Nov 2026 - 13 Dec 2026From$438Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)20 Dec 2026 - 23 Dec 2026From$274Seen: 23 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)10 Jan 2027 - 17 Jan 2027From$274Seen: 4 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 27 Jun 2026From$311Seen: 19 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)16 Jul 2026 - 31 Jul 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)11 Jul 2026 - 12 Jul 2026From$232Seen: 4 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)21 Oct 2026 - 23 Oct 2026From$232Seen: 2 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)07 Oct 2026 - 10 Oct 2026From$242Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)19 Nov 2026 - 19 Nov 2026From$242Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)01 Dec 2026 - 01 Dec 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)02 Jul 2026 - 09 Aug 2026From$361Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)10 Oct 2026 - 15 Oct 2026From$429Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)01 Aug 2026 - 03 Aug 2026From$429Seen: 22 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)31 Jul 2026 - 09 Aug 2026From$330Seen: 16 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Bridgetown, Barbados (BGI)25 Jun 2026 - 03 Jul 2026From$375Seen: 20 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)21 Jun 2026 - 27 Jun 2026From$186Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 25 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.
