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: 15 Dec 2026
From
$129
Seen: 7 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 21 Nov 2026
From
$117
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 10 Nov 2026
From
$185
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 24 Dec 2026
From
$172
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 30 Nov 2026
From
$209
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 05 Jan 2027
From
$159
Seen: 7 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 21 Dec 2026
From
$191
Seen: 13 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 14 Dec 2026
From
$239
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 20 Dec 2026
From
$122
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Dec 2026
From
$213
Seen: 21 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 14 Dec 2026
From
$256
Seen: 19 hrs ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 03 Jan 2027
From
$207
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 | 30 Dec 2026 - 01 Jan 2027 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 16 Jan 2027 - 20 Jan 2027 | From $348 Seen: 12 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 05 Nov 2026 - 05 Nov 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 17 Feb 2027 - 25 Feb 2027 | From $474 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Dec 2026 - 14 Dec 2026 | From $449 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Dec 2026 - 13 Dec 2026 | From $449 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Dec 2026 - 31 Dec 2026 | From $381 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Nov 2026 - 17 Dec 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 21 Dec 2026 - 21 Dec 2026 | From $172 Seen: 19 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 23 Jul 2027 - 01 Aug 2027 | From $314 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 04 Nov 2026 - 04 Dec 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 19 Nov 2026 - 25 Nov 2026 | From $381 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 24 May 2027 - 29 May 2027 | From $314 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 29 Dec 2026 - 05 Jan 2027 | From $441 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 27 Nov 2026 - 02 Dec 2026 | From $441 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Dec 2026 - 13 Dec 2026 | From $468 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 11 Dec 2026 - 15 Dec 2026 | From $468 Seen: 19 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 21 Mar 2027 - 23 Mar 2027 | From $324 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 26 Feb 2027 - 01 Mar 2027 | From $354 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 25 Dec 2026 - 31 Dec 2026 | From $182 Seen: 18 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)30 Dec 2026 - 01 Jan 2027From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)16 Jan 2027 - 20 Jan 2027From$348Seen: 12 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)05 Nov 2026 - 05 Nov 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)17 Feb 2027 - 25 Feb 2027From$474Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)08 Dec 2026 - 14 Dec 2026From$449Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)08 Dec 2026 - 13 Dec 2026From$449Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)01 Dec 2026 - 31 Dec 2026From$381Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)30 Nov 2026 - 17 Dec 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)21 Dec 2026 - 21 Dec 2026From$172Seen: 19 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)23 Jul 2027 - 01 Aug 2027From$314Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)04 Nov 2026 - 04 Dec 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)19 Nov 2026 - 25 Nov 2026From$381Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)24 May 2027 - 29 May 2027From$314Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)29 Dec 2026 - 05 Jan 2027From$441Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)27 Nov 2026 - 02 Dec 2026From$441Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)09 Dec 2026 - 13 Dec 2026From$468Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)11 Dec 2026 - 15 Dec 2026From$468Seen: 19 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)21 Mar 2027 - 23 Mar 2027From$324Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)26 Feb 2027 - 01 Mar 2027From$354Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)25 Dec 2026 - 31 Dec 2026From$182Seen: 18 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.