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: 09 Sep 2026
From
$124
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 25 Nov 2026
From
$146
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 02 Oct 2026
From
$112
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 28 Oct 2026
From
$198
Seen: 5 hrs ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 08 Nov 2026
From
$134
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 23 Oct 2026
From
$102
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 14 Oct 2026
From
$175
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 22 Nov 2026
From
$241
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 08 Sep 2026
From
$117
Seen: 22 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 10 Oct 2026
From
$254
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 28 Nov 2026
From
$229
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Oct 2026
From
$162
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 | 07 Sep 2026 - 10 Sep 2026 | From $186 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 07 Sep 2026 - 07 Sep 2026 | From $186 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 06 Nov 2026 - 08 Nov 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 18 Oct 2026 - 22 Oct 2026 | From $162 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 07 Sep 2026 - 18 Sep 2026 | From $162 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 24 Dec 2026 - 03 Jan 2027 | From $421 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 23 Dec 2026 - 03 Jan 2027 | From $421 Seen: 3 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Dec 2026 - 30 Dec 2026 | From $438 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 31 Dec 2026 - 02 Jan 2027 | From $438 Seen: 8 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 22 Dec 2026 - 29 Dec 2026 | From $264 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Dec 2026 - 26 Dec 2026 | From $421 Seen: 23 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Nov 2026 - 01 Dec 2026 | From $421 Seen: 23 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 23 Dec 2026 - 23 Dec 2026 | From $264 Seen: 4 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 20 Mar 2027 - 26 Mar 2027 | From $294 Seen: 4 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 11 Apr 2027 - 15 Apr 2027 | From $294 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 08 Oct 2026 - 10 Oct 2026 | From $172 Seen: 1 hour ago |
| Bridgetown, Barbados (BGI) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Sep 2026 - 28 Sep 2026 | From $412 Seen: 21 hrs ago |
| Bridgetown, Barbados (BGI) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Oct 2026 - 26 Oct 2026 | From $412 Seen: 15 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Nov 2026 - 30 Nov 2026 | From $438 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Sep 2026 - 27 Sep 2026 | From $429 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)07 Sep 2026 - 10 Sep 2026From$186Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)07 Sep 2026 - 07 Sep 2026From$186Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)06 Nov 2026 - 08 Nov 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)18 Oct 2026 - 22 Oct 2026From$162Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)07 Sep 2026 - 18 Sep 2026From$162Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)24 Dec 2026 - 03 Jan 2027From$421Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)23 Dec 2026 - 03 Jan 2027From$421Seen: 3 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)24 Dec 2026 - 30 Dec 2026From$438Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)31 Dec 2026 - 02 Jan 2027From$438Seen: 8 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)22 Dec 2026 - 29 Dec 2026From$264Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)01 Dec 2026 - 26 Dec 2026From$421Seen: 23 hrs agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)26 Nov 2026 - 01 Dec 2026From$421Seen: 23 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)23 Dec 2026 - 23 Dec 2026From$264Seen: 4 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)20 Mar 2027 - 26 Mar 2027From$294Seen: 4 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)11 Apr 2027 - 15 Apr 2027From$294Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)08 Oct 2026 - 10 Oct 2026From$172Seen: 1 hour agoRound-tripBridgetown, Barbados (BGI)to
Philipsburg, Sint Maarten (SXM)07 Sep 2026 - 28 Sep 2026From$412Seen: 21 hrs agoRound-tripBridgetown, Barbados (BGI)to
Philipsburg, Sint Maarten (SXM)22 Oct 2026 - 26 Oct 2026From$412Seen: 15 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)26 Nov 2026 - 30 Nov 2026From$438Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)22 Sep 2026 - 27 Sep 2026From$429Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.