Find The Best Flight Deals from $28
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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: 14 Oct 2026
From
$89
Seen: 13 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 26 Oct 2026
From
$139
Seen: 14 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 10 Nov 2026
From
$121
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 25 Nov 2026
From
$196
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 06 Nov 2026
From
$109
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Nov 2026
From
$145
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 20 Oct 2026
From
$97
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 22 Oct 2026
From
$72
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 11 Dec 2026
From
$137
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 04 Oct 2026
From
$174
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 13 Nov 2026
From
$309
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Oct 2026
From
$153
Seen: 14 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 | 02 Oct 2026 - 14 Oct 2026 | From $116 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 12 Oct 2026 - 12 Oct 2026 | From $116 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 19 Dec 2026 - 27 Dec 2026 | From $361 Seen: 15 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 04 Dec 2026 - 06 Dec 2026 | From $244 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 13 Mar 2027 - 13 Mar 2027 | From $244 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 29 Oct 2026 - 01 Nov 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 27 Dec 2026 - 03 Jan 2027 | From $348 Seen: 23 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 24 May 2027 - 27 May 2027 | From $214 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 14 May 2027 - 16 May 2027 | From $214 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 06 May 2027 - 12 May 2027 | From $354 Seen: 13 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Dec 2026 - 26 Dec 2026 | From $369 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Dec 2026 - 16 Dec 2026 | From $369 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 09 Oct 2026 - 11 Oct 2026 | From $132 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 02 Oct 2026 - 04 Oct 2026 | From $132 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Oct 2026 - 02 Nov 2026 | From $311 Seen: 14 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Oct 2026 - 03 Nov 2026 | From $361 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Dec 2026 - 18 Dec 2026 | From $311 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 25 Nov 2026 - 29 Nov 2026 | From $311 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 29 Dec 2026 - 10 Feb 2027 | From $554 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 24 Dec 2026 - 27 Dec 2026 | From $311 Seen: 15 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)02 Oct 2026 - 14 Oct 2026From$116Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)12 Oct 2026 - 12 Oct 2026From$116Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)19 Dec 2026 - 27 Dec 2026From$361Seen: 15 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)04 Dec 2026 - 06 Dec 2026From$244Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)13 Mar 2027 - 13 Mar 2027From$244Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)29 Oct 2026 - 01 Nov 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)27 Dec 2026 - 03 Jan 2027From$348Seen: 23 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)24 May 2027 - 27 May 2027From$214Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)14 May 2027 - 16 May 2027From$214Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)06 May 2027 - 12 May 2027From$354Seen: 13 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)08 Dec 2026 - 26 Dec 2026From$369Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)12 Dec 2026 - 16 Dec 2026From$369Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)09 Oct 2026 - 11 Oct 2026From$132Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)02 Oct 2026 - 04 Oct 2026From$132Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)30 Oct 2026 - 02 Nov 2026From$311Seen: 14 hrs agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)01 Oct 2026 - 03 Nov 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)12 Dec 2026 - 18 Dec 2026From$311Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)25 Nov 2026 - 29 Nov 2026From$311Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)29 Dec 2026 - 10 Feb 2027From$554Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)24 Dec 2026 - 27 Dec 2026From$311Seen: 15 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.