Find The Best Flight Deals from $80
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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: 19 Mar 2026
From
$169
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 11 Feb 2026
From
$108
Seen: 21 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 26 Apr 2026
From
$183
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 06 Apr 2026
From
$126
Seen: 4 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 05 Feb 2026
From
$165
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 02 Feb 2026
From
$219
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 25 Mar 2026
From
$142
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)Depart: 22 Mar 2026
From
$154
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 26 Mar 2026
From
$147
Seen: 1 day ago
One-way
Port-of-Spain (POS)to
Philipsburg, Sint Maarten (SXM)Depart: 01 Apr 2026
From
$169
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 08 Apr 2026
From
$114
Seen: 16 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 07 Mar 2026
From
$189
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 | 03 Feb 2026 - 10 Feb 2026 | From $219 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 26 Jan 2026 - 29 Jan 2026 | From $276 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Jun 2026 - 25 Jun 2026 | From $277 Seen: 20 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Jun 2026 - 15 Jun 2026 | From $408 Seen: 19 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Mar 2026 - 29 Mar 2026 | From $408 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 29 Jan 2026 - 19 Feb 2026 | From $276 Seen: 6 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 14 Jul 2026 - 21 Jul 2026 | From $254 Seen: 2 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 Aug 2026 - 15 Aug 2026 | From $409 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 May 2026 - 08 Jun 2026 | From $409 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 21 Mar 2026 - 23 Mar 2026 | From $401 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 02 Apr 2026 - 03 Apr 2026 | From $222 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 03 Mar 2026 - 03 Mar 2026 | From $222 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 15 Aug 2026 - 15 Aug 2026 | From $224 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 06 Mar 2026 - 10 Mar 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 04 Apr 2026 - 12 Apr 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 08 Apr 2026 - 09 Apr 2026 | From $341 Seen: 14 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 06 Aug 2026 - 09 Aug 2026 | From $259 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 03 Jun 2026 - 18 Jun 2026 | From $251 Seen: 6 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 01 Feb 2026 - 07 Feb 2026 | From $386 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 14 Feb 2026 - 15 Feb 2026 | From $232 Seen: 19 hrs 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)03 Feb 2026 - 10 Feb 2026From$219Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)26 Jan 2026 - 29 Jan 2026From$276Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)19 Jun 2026 - 25 Jun 2026From$277Seen: 20 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)11 Jun 2026 - 15 Jun 2026From$408Seen: 19 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)26 Mar 2026 - 29 Mar 2026From$408Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)29 Jan 2026 - 19 Feb 2026From$276Seen: 6 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)14 Jul 2026 - 21 Jul 2026From$254Seen: 2 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)15 Aug 2026 - 15 Aug 2026From$409Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)26 May 2026 - 08 Jun 2026From$409Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)21 Mar 2026 - 23 Mar 2026From$401Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)02 Apr 2026 - 03 Apr 2026From$222Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)03 Mar 2026 - 03 Mar 2026From$222Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)15 Aug 2026 - 15 Aug 2026From$224Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)06 Mar 2026 - 10 Mar 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)04 Apr 2026 - 12 Apr 2026From$341Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)08 Apr 2026 - 09 Apr 2026From$341Seen: 14 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)06 Aug 2026 - 09 Aug 2026From$259Seen: 21 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)03 Jun 2026 - 18 Jun 2026From$251Seen: 6 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)01 Feb 2026 - 07 Feb 2026From$386Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)14 Feb 2026 - 15 Feb 2026From$232Seen: 19 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
