Find The Best Flight Deals from $35
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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: 02 Dec 2026
From
$127
Seen: 5 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 06 Nov 2026
From
$154
Seen: 16 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Dec 2026
From
$82
Seen: 19 hrs ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 21 Dec 2026
From
$72
Seen: 17 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 11 Dec 2026
From
$134
Seen: 5 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 23 Dec 2026
From
$84
Seen: 11 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 13 Dec 2026
From
$90
Seen: 18 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)Depart: 06 Dec 2026
From
$97
Seen: 16 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 06 Dec 2026
From
$139
Seen: 1 day ago
One-way
Charlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)Depart: 24 Nov 2026
From
$55
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Nov 2026
From
$91
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 15 Dec 2026
From
$97
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 |
|---|---|---|---|---|
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 Dec 2026 - 30 Dec 2026 | From $211 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 20 Dec 2026 - 22 Dec 2026 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 16 Dec 2026 - 22 Dec 2026 | From $210 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 04 Dec 2026 - 05 Dec 2026 | From $216 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Dec 2026 - 12 Dec 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 06 Dec 2026 - 08 Dec 2026 | From $224 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Dec 2026 - 26 Dec 2026 | From $211 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 05 Dec 2026 - 17 Dec 2026 | From $216 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Marigot, Dominica (DOM) | Round-trip | 04 Dec 2026 - 11 Dec 2026 | From $179 Seen: 16 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Dec 2026 - 04 Dec 2026 | From $259 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Dec 2026 - 15 Dec 2026 | From $259 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 17 Dec 2026 - 20 Dec 2026 | From $210 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Dec 2026 - 16 Dec 2026 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 04 Dec 2026 - 06 Dec 2026 | From $132 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 07 Dec 2026 - 12 Dec 2026 | From $211 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 14 Dec 2026 - 21 Dec 2026 | From $211 Seen: 1 day ago |
| Charlestown, Nevis (NEV) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Nov 2026 - 14 Nov 2026 | From $199 Seen: 1 day ago |
| Charlestown, Nevis (NEV) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Nov 2026 - 09 Nov 2026 | From $199 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Marigot, Dominica (DOM) | Round-trip | 22 Dec 2026 - 25 Dec 2026 | From $179 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Philipsburg, Sint Maarten (SXM) | Round-trip | 23 Dec 2026 - 29 Dec 2026 | From $224 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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Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)15 Dec 2026 - 30 Dec 2026From$211Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)20 Dec 2026 - 22 Dec 2026From$210Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)16 Dec 2026 - 22 Dec 2026From$210Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)04 Dec 2026 - 05 Dec 2026From$216Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)07 Dec 2026 - 12 Dec 2026From$216Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)06 Dec 2026 - 08 Dec 2026From$224Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)24 Dec 2026 - 26 Dec 2026From$211Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)05 Dec 2026 - 17 Dec 2026From$216Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)04 Dec 2026 - 11 Dec 2026From$179Seen: 16 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)01 Dec 2026 - 04 Dec 2026From$259Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)12 Dec 2026 - 15 Dec 2026From$259Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)17 Dec 2026 - 20 Dec 2026From$210Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)09 Dec 2026 - 16 Dec 2026From$210Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)04 Dec 2026 - 06 Dec 2026From$132Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)07 Dec 2026 - 12 Dec 2026From$211Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)14 Dec 2026 - 21 Dec 2026From$211Seen: 1 day agoRound-tripCharlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)03 Nov 2026 - 14 Nov 2026From$199Seen: 1 day agoRound-tripCharlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)03 Nov 2026 - 09 Nov 2026From$199Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)22 Dec 2026 - 25 Dec 2026From$179Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Philipsburg, Sint Maarten (SXM)23 Dec 2026 - 29 Dec 2026From$224Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.