Find The Best Flight Deals from $35
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1 Passenger
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Travel Throughout the Caribbean with Winair, with these best one way flight deals
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Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Oct 2026
From
$82
Seen: 20 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 19 Oct 2026
From
$127
Seen: 19 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 18 Oct 2026
From
$144
Seen: 22 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)Depart: 16 Oct 2026
From
$97
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 16 Oct 2026
From
$134
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 08 Oct 2026
From
$84
Seen: 1 day ago
One-way
Bridgetown, Barbados (BGI)to
Philipsburg, Sint Maarten (SXM)Depart: 19 Oct 2026
From
$86
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Road Town, Tortola (EIS)Depart: 12 Oct 2026
From
$102
Seen: 8 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 22 Oct 2026
From
$97
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 18 Oct 2026
From
$64
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 11 Oct 2026
From
$72
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 07 Oct 2026
From
$139
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 |
|---|---|---|---|---|
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 04 Oct 2026 - 10 Oct 2026 | From $216 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Oct 2026 - 26 Oct 2026 | From $211 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 02 Oct 2026 - 06 Oct 2026 | From $211 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Marigot, Dominica (DOM) | Round-trip | 02 Oct 2026 - 05 Oct 2026 | From $179 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 02 Oct 2026 - 05 Oct 2026 | From $216 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 28 Oct 2026 - 30 Oct 2026 | From $210 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Oct 2026 - 18 Oct 2026 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 18 Oct 2026 - 18 Oct 2026 | From $132 Seen: 23 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 10 Oct 2026 - 15 Oct 2026 | From $124 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Road Town, Tortola (EIS) | Round-trip | 17 Oct 2026 - 20 Oct 2026 | From $207 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Oct 2026 - 13 Oct 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 21 Oct 2026 - 30 Oct 2026 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 07 Oct 2026 - 14 Oct 2026 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 27 Oct 2026 - 30 Oct 2026 | From $132 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 10 Oct 2026 - 14 Oct 2026 | From $124 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 04 Oct 2026 - 11 Oct 2026 | From $211 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 29 Oct 2026 - 31 Oct 2026 | From $211 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 23 Oct 2026 - 25 Oct 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 03 Oct 2026 - 15 Oct 2026 | From $224 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 06 Oct 2026 - 12 Oct 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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Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)04 Oct 2026 - 10 Oct 2026From$216Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)22 Oct 2026 - 26 Oct 2026From$211Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)02 Oct 2026 - 06 Oct 2026From$211Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Marigot, Dominica (DOM)02 Oct 2026 - 05 Oct 2026From$179Seen: 22 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)02 Oct 2026 - 05 Oct 2026From$216Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)28 Oct 2026 - 30 Oct 2026From$210Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)13 Oct 2026 - 18 Oct 2026From$210Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)18 Oct 2026 - 18 Oct 2026From$132Seen: 23 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)10 Oct 2026 - 15 Oct 2026From$124Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Road Town, Tortola (EIS)17 Oct 2026 - 20 Oct 2026From$207Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)09 Oct 2026 - 13 Oct 2026From$216Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)21 Oct 2026 - 30 Oct 2026From$210Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)07 Oct 2026 - 14 Oct 2026From$210Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)27 Oct 2026 - 30 Oct 2026From$132Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)10 Oct 2026 - 14 Oct 2026From$124Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)04 Oct 2026 - 11 Oct 2026From$211Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)29 Oct 2026 - 31 Oct 2026From$211Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)23 Oct 2026 - 25 Oct 2026From$216Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)03 Oct 2026 - 15 Oct 2026From$224Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)06 Oct 2026 - 12 Oct 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.