Find The Best Flight Deals from $30
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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
Willemstad, Curacao (CUR)Depart: 20 May 2026
From
$122
Seen: 7 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 09 Jun 2026
From
$124
Seen: 10 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 20 May 2026
From
$79
Seen: 8 hrs ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 09 Jun 2026
From
$30
Seen: 6 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 25 Apr 2026
From
$169
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 19 Jun 2026
From
$54
Seen: 6 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 05 Jun 2026
From
$92
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 12 Jun 2026
From
$72
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 16 Jun 2026
From
$129
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 11 Jun 2026
From
$92
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 23 Jun 2026
From
$62
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 24 Jun 2026
From
$129
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) | Oranjestad, Aruba (AUA) | Round-trip | 23 Jun 2026 - 28 Jun 2026 | From $194 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 07 Jun 2026 - 14 Jun 2026 | From $194 Seen: 3 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 May 2026 - 20 May 2026 | From $200 Seen: 5 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 05 Jun 2026 - 09 Jun 2026 | From $122 Seen: 13 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 05 Jun 2026 - 09 Jun 2026 | From $122 Seen: 5 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Jun 2026 - 29 Jun 2026 | From $122 Seen: 6 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Jun 2026 - 08 Jun 2026 | From $122 Seen: 13 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 05 Jun 2026 - 07 Jun 2026 | From $104 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 02 Jul 2026 - 10 Jul 2026 | From $276 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 17 Jul 2026 - 17 Jul 2026 | From $276 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 04 Jun 2026 - 09 Jun 2026 | From $122 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 20 May 2026 - 20 May 2026 | From $200 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 29 Apr 2026 - 09 May 2026 | From $210 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Jun 2026 - 07 Jun 2026 | From $196 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 20 Jun 2026 - 27 Jun 2026 | From $196 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 06 May 2026 - 10 May 2026 | From $200 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 19 Jun 2026 - 28 Jun 2026 | From $191 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 01 Jun 2026 - 25 Jun 2026 | From $191 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 04 Jun 2026 - 27 Jun 2026 | From $196 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 08 Jun 2026 - 09 Jun 2026 | From $196 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
Oranjestad, Aruba (AUA)23 Jun 2026 - 28 Jun 2026From$194Seen: 8 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)07 Jun 2026 - 14 Jun 2026From$194Seen: 3 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)15 May 2026 - 20 May 2026From$200Seen: 5 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)05 Jun 2026 - 09 Jun 2026From$122Seen: 13 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)05 Jun 2026 - 09 Jun 2026From$122Seen: 5 hrs agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)05 Jun 2026 - 29 Jun 2026From$122Seen: 6 hrs agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)05 Jun 2026 - 08 Jun 2026From$122Seen: 13 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)05 Jun 2026 - 07 Jun 2026From$104Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)02 Jul 2026 - 10 Jul 2026From$276Seen: 16 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)17 Jul 2026 - 17 Jul 2026From$276Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)04 Jun 2026 - 09 Jun 2026From$122Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)20 May 2026 - 20 May 2026From$200Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)29 Apr 2026 - 09 May 2026From$210Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)05 Jun 2026 - 07 Jun 2026From$196Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)20 Jun 2026 - 27 Jun 2026From$196Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)06 May 2026 - 10 May 2026From$200Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)19 Jun 2026 - 28 Jun 2026From$191Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)01 Jun 2026 - 25 Jun 2026From$191Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)04 Jun 2026 - 27 Jun 2026From$196Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)08 Jun 2026 - 09 Jun 2026From$196Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
