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: 30 Jun 2026
From
$124
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 30 Jun 2026
From
$62
Seen: 3 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 27 Aug 2026
From
$229
Seen: 23 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 28 Jul 2026
From
$112
Seen: 21 hrs ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 05 Sep 2026
From
$141
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 09 Sep 2026
From
$192
Seen: 23 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Depart: 20 Jul 2026
From
$224
Seen: 2 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 08 Sep 2026
From
$241
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 19 Jul 2026
From
$117
Seen: 20 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 03 Aug 2026
From
$199
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 17 Sep 2026
From
$198
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 06 Sep 2026
From
$175
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 | 25 Jun 2026 - 25 Jun 2026 | From $186 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 26 Jun 2026 - 26 Jun 2026 | From $186 Seen: 13 minutes ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 05 Aug 2026 - 06 Aug 2026 | From $162 Seen: 4 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Jun 2026 - 25 Jun 2026 | From $186 Seen: 4 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Jun 2026 - 24 Jun 2026 | From $186 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 28 Oct 2026 - 02 Nov 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 24 Jun 2026 - 24 Jun 2026 | From $421 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 15 Jul 2026 - 16 Jul 2026 | From $162 Seen: 18 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 01 Dec 2026 - 09 Dec 2026 | From $274 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 01 Dec 2026 - 03 Dec 2026 | From $274 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 26 Jun 2026 - 10 Jul 2026 | From $421 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 09 Sep 2026 - 14 Sep 2026 | From $421 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 06 Jul 2026 - 21 Jul 2026 | From $384 Seen: 43 minutes ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Nov 2026 - 07 Nov 2026 | From $438 Seen: 23 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 05 Nov 2026 - 08 Nov 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 29 Aug 2026 - 09 Oct 2026 | From $438 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 20 Jul 2026 - 21 Jul 2026 | From $172 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 10 Oct 2026 - 16 Oct 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 04 Sep 2026 - 06 Sep 2026 | From $361 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | 06 Jul 2026 - 14 Jul 2026 | From $384 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)25 Jun 2026 - 25 Jun 2026From$186Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)26 Jun 2026 - 26 Jun 2026From$186Seen: 13 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)05 Aug 2026 - 06 Aug 2026From$162Seen: 4 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)25 Jun 2026 - 25 Jun 2026From$186Seen: 4 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)24 Jun 2026 - 24 Jun 2026From$186Seen: 1 hour agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)28 Oct 2026 - 02 Nov 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)24 Jun 2026 - 24 Jun 2026From$421Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)15 Jul 2026 - 16 Jul 2026From$162Seen: 18 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)01 Dec 2026 - 09 Dec 2026From$274Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)01 Dec 2026 - 03 Dec 2026From$274Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)26 Jun 2026 - 10 Jul 2026From$421Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)09 Sep 2026 - 14 Sep 2026From$421Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)06 Jul 2026 - 21 Jul 2026From$384Seen: 43 minutes agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)01 Nov 2026 - 07 Nov 2026From$438Seen: 23 minutes agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)05 Nov 2026 - 08 Nov 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)29 Aug 2026 - 09 Oct 2026From$438Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)20 Jul 2026 - 21 Jul 2026From$172Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)10 Oct 2026 - 16 Oct 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)04 Sep 2026 - 06 Sep 2026From$361Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)06 Jul 2026 - 14 Jul 2026From$384Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.