Find The Best Flight Deals from $55
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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: 05 Dec 2026
From
$204
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Jan 2027
From
$172
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 24 Oct 2026
From
$179
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 30 Dec 2026
From
$191
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 28 Nov 2026
From
$117
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 15 Nov 2026
From
$256
Seen: 16 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 24 Dec 2026
From
$185
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 13 Nov 2026
From
$209
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 22 Nov 2026
From
$159
Seen: 11 hrs ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Oct 2026
From
$142
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 27 Dec 2026
From
$122
Seen: 16 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Dec 2026
From
$213
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 | 26 Oct 2026 - 30 Oct 2026 | From $206 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 30 Oct 2026 - 30 Oct 2026 | From $206 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Nov 2026 - 30 Nov 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 19 Oct 2026 - 23 Oct 2026 | From $416 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 21 Oct 2026 - 06 Nov 2026 | From $421 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 10 Sep 2027 - 20 Sep 2027 | From $314 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 13 Sep 2027 - 15 Sep 2027 | From $284 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 01 Nov 2026 - 01 Nov 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 17 Dec 2026 - 20 Dec 2026 | From $468 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 13 Nov 2026 - 16 Nov 2026 | From $172 Seen: 10 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Nov 2026 - 10 Nov 2026 | From $381 Seen: 11 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 11 Dec 2026 - 15 Dec 2026 | From $468 Seen: 14 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Dec 2026 - 14 Dec 2026 | From $449 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Nov 2026 - 29 Nov 2026 | From $449 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 25 Dec 2026 - 28 Dec 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 09 Dec 2026 - 08 Jan 2027 | From $381 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 08 May 2027 - 11 May 2027 | From $284 Seen: 15 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 27 Oct 2026 - 03 Nov 2026 | From $311 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Feb 2027 - 10 Feb 2027 | From $418 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 29 Dec 2026 - 30 Dec 2026 | From $182 Seen: 17 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)26 Oct 2026 - 30 Oct 2026From$206Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)30 Oct 2026 - 30 Oct 2026From$206Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Nov 2026 - 30 Nov 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)19 Oct 2026 - 23 Oct 2026From$416Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)21 Oct 2026 - 06 Nov 2026From$421Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)10 Sep 2027 - 20 Sep 2027From$314Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)13 Sep 2027 - 15 Sep 2027From$284Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)01 Nov 2026 - 01 Nov 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)17 Dec 2026 - 20 Dec 2026From$468Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)13 Nov 2026 - 16 Nov 2026From$172Seen: 10 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)03 Nov 2026 - 10 Nov 2026From$381Seen: 11 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)11 Dec 2026 - 15 Dec 2026From$468Seen: 14 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)11 Dec 2026 - 14 Dec 2026From$449Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)26 Nov 2026 - 29 Nov 2026From$449Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)25 Dec 2026 - 28 Dec 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)09 Dec 2026 - 08 Jan 2027From$381Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)08 May 2027 - 11 May 2027From$284Seen: 15 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)27 Oct 2026 - 03 Nov 2026From$311Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)05 Feb 2027 - 10 Feb 2027From$418Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)29 Dec 2026 - 30 Dec 2026From$182Seen: 17 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.