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: 14 May 2026
From
$169
Seen: 21 hrs ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 28 May 2026
From
$107
Seen: 13 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 12 May 2026
From
$142
Seen: 20 hrs ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Mar 2026
From
$183
Seen: 2 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 05 Apr 2026
From
$262
Seen: 5 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 01 Apr 2026
From
$147
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 25 Apr 2026
From
$189
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 08 Apr 2026
From
$152
Seen: 15 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 02 Jun 2026
From
$126
Seen: 6 hrs ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 02 May 2026
From
$85
Seen: 1 day ago
One-way
The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Depart: 14 May 2026
From
$80
Seen: 15 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 16 Apr 2026
From
$219
Seen: 21 hrs 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 | 29 Oct 2026 - 05 Nov 2026 | From $229 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 01 Jun 2026 - 05 Jun 2026 | From $276 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 13 Aug 2026 - 20 Aug 2026 | From $408 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Nov 2026 - 28 Nov 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 16 Jun 2026 - 16 Jun 2026 | From $222 Seen: 3 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 07 Apr 2026 - 10 Apr 2026 | From $276 Seen: 5 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 Apr 2026 - 22 Apr 2026 | From $321 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 03 Dec 2026 - 14 Dec 2026 | From $222 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 17 May 2026 - 24 May 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 12 May 2026 - 19 May 2026 | From $341 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 20 Jul 2026 - 27 Jul 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 24 Dec 2026 - 02 Jan 2027 | From $408 Seen: 56 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 28 Mar 2026 - 04 Apr 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 25 Mar 2026 - 01 Apr 2026 | From $232 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 24 Dec 2026 - 01 Jan 2027 | From $224 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 12 Oct 2026 - 16 Oct 2026 | From $254 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 11 Sep 2026 - 14 Sep 2026 | From $259 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 29 Jun 2026 - 31 Jul 2026 | From $408 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 19 Jun 2026 - 22 Jun 2026 | From $341 Seen: 23 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 10 Jan 2027 - 19 Jan 2027 | From $224 Seen: 4 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)29 Oct 2026 - 05 Nov 2026From$229Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)01 Jun 2026 - 05 Jun 2026From$276Seen: 22 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)13 Aug 2026 - 20 Aug 2026From$408Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)24 Nov 2026 - 28 Nov 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)16 Jun 2026 - 16 Jun 2026From$222Seen: 3 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)07 Apr 2026 - 10 Apr 2026From$276Seen: 5 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)15 Apr 2026 - 22 Apr 2026From$321Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)03 Dec 2026 - 14 Dec 2026From$222Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)17 May 2026 - 24 May 2026From$341Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)12 May 2026 - 19 May 2026From$341Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)20 Jul 2026 - 27 Jul 2026From$341Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)24 Dec 2026 - 02 Jan 2027From$408Seen: 56 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)28 Mar 2026 - 04 Apr 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)25 Mar 2026 - 01 Apr 2026From$232Seen: 18 hrs agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)24 Dec 2026 - 01 Jan 2027From$224Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)12 Oct 2026 - 16 Oct 2026From$254Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)11 Sep 2026 - 14 Sep 2026From$259Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)29 Jun 2026 - 31 Jul 2026From$408Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)19 Jun 2026 - 22 Jun 2026From$341Seen: 23 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)10 Jan 2027 - 19 Jan 2027From$224Seen: 4 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
