Find The Best Flight Deals from $79
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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 Jun 2026
From
$169
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 29 May 2026
From
$108
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 09 May 2026
From
$142
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 01 Jul 2026
From
$226
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 06 May 2026
From
$165
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 05 Jun 2026
From
$147
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 04 May 2026
From
$182
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 02 Jun 2026
From
$131
Seen: 2 hrs ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 15 Jun 2026
From
$119
Seen: 43 minutes ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 27 May 2026
From
$183
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 05 May 2026
From
$152
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 07 Jun 2026
From
$85
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 | 04 Jun 2026 - 11 Jun 2026 | From $277 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 20 Jun 2026 - 25 Jun 2026 | From $277 Seen: 19 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 Oct 2026 - 23 Oct 2026 | From $408 Seen: 22 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 May 2026 - 20 Oct 2026 | From $312 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 18 May 2026 - 21 May 2026 | From $277 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 19 Aug 2026 - 19 Aug 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 09 Sep 2026 - 27 Sep 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 13 May 2026 - 15 May 2026 | From $222 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 15 May 2026 - 15 May 2026 | From $222 Seen: 17 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Apr 2026 - 30 Apr 2026 | From $409 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Aug 2026 - 26 Aug 2026 | From $409 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 12 Nov 2026 - 17 Nov 2026 | From $232 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jun 2026 - 07 Jun 2026 | From $401 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 19 Jun 2026 - 22 Jun 2026 | From $232 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 May 2026 - 16 May 2026 | From $232 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jul 2026 - 08 Jul 2026 | From $408 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 07 Sep 2026 - 07 Sep 2026 | From $254 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 03 Sep 2026 - 07 Sep 2026 | From $259 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 23 Oct 2026 - 23 Oct 2026 | From $224 Seen: 21 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 23 Oct 2026 - 25 Oct 2026 | From $224 Seen: 21 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)04 Jun 2026 - 11 Jun 2026From$277Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)20 Jun 2026 - 25 Jun 2026From$277Seen: 19 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)16 Oct 2026 - 23 Oct 2026From$408Seen: 22 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)30 May 2026 - 20 Oct 2026From$312Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)18 May 2026 - 21 May 2026From$277Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)19 Aug 2026 - 19 Aug 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)09 Sep 2026 - 27 Sep 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)13 May 2026 - 15 May 2026From$222Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)15 May 2026 - 15 May 2026From$222Seen: 17 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)26 Apr 2026 - 30 Apr 2026From$409Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)21 Aug 2026 - 26 Aug 2026From$409Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)12 Nov 2026 - 17 Nov 2026From$232Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)01 Jun 2026 - 07 Jun 2026From$401Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)19 Jun 2026 - 22 Jun 2026From$232Seen: 1 day agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)16 May 2026 - 16 May 2026From$232Seen: 22 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)01 Jul 2026 - 08 Jul 2026From$408Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)07 Sep 2026 - 07 Sep 2026From$254Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)03 Sep 2026 - 07 Sep 2026From$259Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)23 Oct 2026 - 23 Oct 2026From$224Seen: 21 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)23 Oct 2026 - 25 Oct 2026From$224Seen: 21 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.