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: 20 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 02 Feb 2027
From
$181
Seen: 21 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 25 Nov 2026
From
$117
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 14 Jan 2027
From
$172
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 07 Jan 2027
From
$182
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 10 Dec 2026
From
$256
Seen: 10 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 06 Nov 2026
From
$239
Seen: 12 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 26 Dec 2026
From
$209
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 05 Dec 2026
From
$185
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 04 Feb 2027
From
$159
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Feb 2027
From
$213
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 22 Dec 2026
From
$122
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 | 14 Mar 2027 - 23 Mar 2027 | From $319 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 24 Feb 2027 - 01 Mar 2027 | From $393 Seen: 22 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 01 Jun 2027 - 06 Jun 2027 | From $314 Seen: 21 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 05 Jul 2027 - 09 Jul 2027 | From $314 Seen: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 26 Nov 2026 - 26 Nov 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 13 Nov 2026 - 15 Nov 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 01 Dec 2026 - 31 Dec 2026 | From $468 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 21 Dec 2026 - 01 Jan 2027 | From $441 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 29 Mar 2027 - 05 Apr 2027 | From $299 Seen: 19 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Dec 2026 - 28 Dec 2026 | From $381 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Dec 2026 - 19 Dec 2026 | From $381 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 02 Jan 2027 - 09 Jan 2027 | From $558 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 25 Nov 2026 - 02 Dec 2026 | From $468 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 26 Nov 2026 - 28 Nov 2026 | From $441 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 13 Nov 2026 - 16 Nov 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 12 Nov 2026 - 16 Nov 2026 | From $381 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Dec 2026 - 24 Dec 2026 | From $449 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Nov 2026 - 19 Nov 2026 | From $449 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 25 Feb 2027 - 03 Mar 2027 | From $334 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Feb 2027 - 02 Feb 2027 | From $474 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)14 Mar 2027 - 23 Mar 2027From$319Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)24 Feb 2027 - 01 Mar 2027From$393Seen: 22 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)01 Jun 2027 - 06 Jun 2027From$314Seen: 21 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)05 Jul 2027 - 09 Jul 2027From$314Seen: 15 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)26 Nov 2026 - 26 Nov 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)13 Nov 2026 - 15 Nov 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)01 Dec 2026 - 31 Dec 2026From$468Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)21 Dec 2026 - 01 Jan 2027From$441Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)29 Mar 2027 - 05 Apr 2027From$299Seen: 19 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Dec 2026 - 28 Dec 2026From$381Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)13 Dec 2026 - 19 Dec 2026From$381Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)02 Jan 2027 - 09 Jan 2027From$558Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)25 Nov 2026 - 02 Dec 2026From$468Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)26 Nov 2026 - 28 Nov 2026From$441Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)13 Nov 2026 - 16 Nov 2026From$381Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)12 Nov 2026 - 16 Nov 2026From$381Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)21 Dec 2026 - 24 Dec 2026From$449Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)17 Nov 2026 - 19 Nov 2026From$449Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)25 Feb 2027 - 03 Mar 2027From$334Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)01 Feb 2027 - 02 Feb 2027From$474Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.