Find The Best Flight Deals from $50
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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: 31 Jul 2026
From
$124
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 29 Jul 2026
From
$162
Seen: 23 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 21 Sep 2026
From
$112
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 19 Aug 2026
From
$229
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 05 Aug 2026
From
$192
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Jul 2026
From
$175
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 25 Jul 2026
From
$117
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 27 Aug 2026
From
$198
Seen: 23 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 17 Aug 2026
From
$141
Seen: 6 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 09 Jul 2026
From
$199
Seen: 14 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 13 Sep 2026
From
$241
Seen: 12 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 13 Jul 2026
From
$224
Seen: 8 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 | 01 Aug 2026 - 08 Aug 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 16 Jul 2026 - 16 Jul 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 27 Aug 2026 - 31 Aug 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 22 Oct 2026 - 01 Nov 2026 | From $421 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Sep 2026 - 27 Sep 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 06 Aug 2026 - 12 Aug 2026 | From $162 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 04 Jul 2026 - 04 Jul 2026 | From $162 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Jul 2026 - 13 Aug 2026 | From $421 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Aug 2026 - 16 Sep 2026 | From $421 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 28 Sep 2026 - 28 Sep 2026 | From $361 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Sep 2026 - 25 Sep 2026 | From $429 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 06 Jul 2026 - 14 Jul 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 21 Jul 2026 - 25 Jul 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 12 Nov 2026 - 15 Nov 2026 | From $438 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Dec 2026 - 14 Dec 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 04 Nov 2026 - 05 Dec 2026 | From $644 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 28 Oct 2026 - 01 Nov 2026 | From $361 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 14 Jul 2026 - 19 Jul 2026 | From $429 Seen: 4 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 18 Jan 2027 - 21 Jan 2027 | From $274 Seen: 4 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 10 Feb 2027 - 11 Feb 2027 | From $274 Seen: 22 minutes 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)01 Aug 2026 - 08 Aug 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)16 Jul 2026 - 16 Jul 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)27 Aug 2026 - 31 Aug 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)22 Oct 2026 - 01 Nov 2026From$421Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)24 Sep 2026 - 27 Sep 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)06 Aug 2026 - 12 Aug 2026From$162Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)04 Jul 2026 - 04 Jul 2026From$162Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)13 Jul 2026 - 13 Aug 2026From$421Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)12 Aug 2026 - 16 Sep 2026From$421Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)28 Sep 2026 - 28 Sep 2026From$361Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)19 Sep 2026 - 25 Sep 2026From$429Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)06 Jul 2026 - 14 Jul 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)21 Jul 2026 - 25 Jul 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)12 Nov 2026 - 15 Nov 2026From$438Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)07 Dec 2026 - 14 Dec 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)04 Nov 2026 - 05 Dec 2026From$644Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)28 Oct 2026 - 01 Nov 2026From$361Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)14 Jul 2026 - 19 Jul 2026From$429Seen: 4 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)18 Jan 2027 - 21 Jan 2027From$274Seen: 4 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)10 Feb 2027 - 11 Feb 2027From$274Seen: 22 minutes agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.