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: 31 Mar 2026
From
$169
Seen: 23 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 16 Feb 2026
From
$142
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 15 Mar 2026
From
$108
Seen: 13 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 22 Jan 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 06 Jan 2026
From
$189
Seen: 23 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 15 Feb 2026
From
$180
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 23 Mar 2026
From
$114
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Charlestown, Nevis (NEV)Depart: 16 Feb 2026
From
$214
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 05 Mar 2026
From
$138
Seen: 1 day ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 10 Jan 2026
From
$85
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 09 Jan 2026
From
$336
Seen: 21 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Depart: 03 Apr 2026
From
$224
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 | 22 Apr 2026 - 26 Apr 2026 | From $277 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 16 Feb 2026 - 16 Feb 2026 | From $184 Seen: 11 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Mar 2026 - 17 Mar 2026 | From $277 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 15 Apr 2026 - 18 Apr 2026 | From $222 Seen: 2 days ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 15 Jan 2026 - 16 Jan 2026 | From $222 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 12 Jan 2026 - 24 Jan 2026 | From $277 Seen: 11 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Mar 2026 - 29 Mar 2026 | From $402 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 02 Apr 2026 - 07 Apr 2026 | From $396 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Apr 2026 - 18 Apr 2026 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 09 May 2026 - 16 May 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 28 Feb 2026 - 13 Mar 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 06 Jan 2026 - 18 Feb 2026 | From $368 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 16 Mar 2026 - 20 Mar 2026 | From $402 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Charlestown, Nevis (NEV) | Round-trip | 05 Apr 2026 - 09 Apr 2026 | From $339 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Charlestown, Nevis (NEV) | Round-trip | 29 Mar 2026 - 09 Apr 2026 | From $349 Seen: 14 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 07 Oct 2026 - 11 Oct 2026 | From $266 Seen: 22 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 25 Apr 2026 - 30 Apr 2026 | From $271 Seen: 23 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 29 Jun 2026 - 30 Jun 2026 | From $236 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 06 Mar 2026 - 11 Mar 2026 | From $341 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 06 Jan 2026 - 21 Jan 2026 | From $368 Seen: 7 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)22 Apr 2026 - 26 Apr 2026From$277Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)16 Feb 2026 - 16 Feb 2026From$184Seen: 11 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)12 Mar 2026 - 17 Mar 2026From$277Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)15 Apr 2026 - 18 Apr 2026From$222Seen: 2 days agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)15 Jan 2026 - 16 Jan 2026From$222Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)12 Jan 2026 - 24 Jan 2026From$277Seen: 11 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)22 Mar 2026 - 29 Mar 2026From$402Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)02 Apr 2026 - 07 Apr 2026From$396Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)11 Apr 2026 - 18 Apr 2026From$396Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)09 May 2026 - 16 May 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)28 Feb 2026 - 13 Mar 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)06 Jan 2026 - 18 Feb 2026From$368Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)16 Mar 2026 - 20 Mar 2026From$402Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Charlestown, Nevis (NEV)05 Apr 2026 - 09 Apr 2026From$339Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Charlestown, Nevis (NEV)29 Mar 2026 - 09 Apr 2026From$349Seen: 14 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)07 Oct 2026 - 11 Oct 2026From$266Seen: 22 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)25 Apr 2026 - 30 Apr 2026From$271Seen: 23 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)29 Jun 2026 - 30 Jun 2026From$236Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)06 Mar 2026 - 11 Mar 2026From$341Seen: 22 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)06 Jan 2026 - 21 Jan 2026From$368Seen: 7 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.