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: 03 Sep 2026
From
$124
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 10 Oct 2026
From
$229
Seen: 17 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 14 Sep 2026
From
$112
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 12 Sep 2026
From
$162
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 15 Oct 2026
From
$151
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 12 Oct 2026
From
$134
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Aug 2026
From
$55
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Oct 2026
From
$198
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 02 Nov 2026
From
$241
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Nov 2026
From
$175
Seen: 11 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)Depart: 01 Oct 2026
From
$179
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 09 Nov 2026
From
$192
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 | 02 Sep 2026 - 30 Sep 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 17 Aug 2026 - 18 Aug 2026 | From $186 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 26 Oct 2026 - 26 Oct 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 29 Oct 2026 - 20 Dec 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 28 Aug 2026 - 28 Aug 2026 | From $162 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 27 Aug 2026 - 28 Aug 2026 | From $162 Seen: 18 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Sep 2026 - 21 Sep 2026 | From $361 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 10 Nov 2026 - 15 Nov 2026 | From $361 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 05 Sep 2026 - 12 Sep 2026 | From $429 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Nov 2026 - 30 Nov 2026 | From $429 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 26 May 2027 - 09 Jun 2027 | From $294 Seen: 8 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 28 Oct 2026 - 03 Nov 2026 | From $294 Seen: 1 hour ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Sep 2026 - 25 Sep 2026 | From $172 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jan 2027 - 08 Jan 2027 | From $444 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 29 Dec 2026 - 01 Aug 2027 | From $438 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 30 Dec 2026 - 01 Jan 2027 | From $438 Seen: 14 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 25 Dec 2026 - 30 Dec 2026 | From $264 Seen: 10 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 18 Nov 2026 - 25 Nov 2026 | From $264 Seen: 10 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 04 Oct 2026 - 24 Jul 2027 | From $374 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Nov 2026 - 08 Nov 2026 | From $421 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)02 Sep 2026 - 30 Sep 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)17 Aug 2026 - 18 Aug 2026From$186Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)26 Oct 2026 - 26 Oct 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)29 Oct 2026 - 20 Dec 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)28 Aug 2026 - 28 Aug 2026From$162Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)27 Aug 2026 - 28 Aug 2026From$162Seen: 18 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)19 Sep 2026 - 21 Sep 2026From$361Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)10 Nov 2026 - 15 Nov 2026From$361Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)05 Sep 2026 - 12 Sep 2026From$429Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)26 Nov 2026 - 30 Nov 2026From$429Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)26 May 2027 - 09 Jun 2027From$294Seen: 8 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)28 Oct 2026 - 03 Nov 2026From$294Seen: 1 hour agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)09 Sep 2026 - 25 Sep 2026From$172Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)01 Jan 2027 - 08 Jan 2027From$444Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)29 Dec 2026 - 01 Aug 2027From$438Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)30 Dec 2026 - 01 Jan 2027From$438Seen: 14 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)25 Dec 2026 - 30 Dec 2026From$264Seen: 10 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)18 Nov 2026 - 25 Nov 2026From$264Seen: 10 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)04 Oct 2026 - 24 Jul 2027From$374Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)03 Nov 2026 - 08 Nov 2026From$421Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.