Find The Best Flight Deals from $45
expand_more
1 Passenger
expand_moretoday
today
Travel Throughout the Caribbean with Winair, with these best one way flight deals
flight_takeoff
flight_land
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Depart: 25 Apr 2026
From
$169
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Depart: 14 May 2026
From
$183
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Depart: 01 May 2026
From
$147
Seen: 1 day ago
One-way
Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Depart: 25 Mar 2026
From
$147
Seen: 19 hrs ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 16 Mar 2026
From
$165
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 17 May 2026
From
$119
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Depart: 22 Apr 2026
From
$226
Seen: 3 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 13 Mar 2026
From
$107
Seen: 9 hrs ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 06 Jun 2026
From
$189
Seen: 1 day ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 22 Mar 2026
From
$108
Seen: 10 hrs ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 02 May 2026
From
$152
Seen: 1 day ago
One-way
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Depart: 06 Jun 2026
From
$126
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
flight_takeoff
flight_land
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 18 Apr 2026 - 18 Apr 2026 | From $184 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 10 Mar 2026 - 15 Mar 2026 | From $276 Seen: 10 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 20 May 2026 - 21 May 2026 | From $408 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 21 Jun 2026 - 12 Jul 2026 | From $408 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 22 Mar 2026 - 29 Mar 2026 | From $232 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 03 Apr 2026 - 03 Apr 2026 | From $232 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 31 Jul 2026 - 24 Aug 2026 | From $401 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Jul 2026 - 26 Jul 2026 | From $401 Seen: 14 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 15 May 2026 - 19 May 2026 | From $409 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 May 2026 - 16 May 2026 | From $409 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 15 Oct 2026 - 19 Oct 2026 | From $224 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 03 May 2026 - 06 May 2026 | From $234 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 11 Oct 2026 - 17 Oct 2026 | From $408 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 13 Jul 2026 - 16 Aug 2026 | From $408 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 17 Jun 2026 - 17 Jun 2026 | From $222 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 05 May 2026 - 12 May 2026 | From $222 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 16 Jun 2026 - 16 Jun 2026 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 17 Jun 2026 - 17 Jun 2026 | From $341 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 08 Apr 2026 - 08 Apr 2026 | From $286 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 11 Apr 2026 - 15 Apr 2026 | From $321 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
flight_takeoff
flight_land
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)18 Apr 2026 - 18 Apr 2026From$184Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)10 Mar 2026 - 15 Mar 2026From$276Seen: 10 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)20 May 2026 - 21 May 2026From$408Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)21 Jun 2026 - 12 Jul 2026From$408Seen: 16 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)22 Mar 2026 - 29 Mar 2026From$232Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)03 Apr 2026 - 03 Apr 2026From$232Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)31 Jul 2026 - 24 Aug 2026From$401Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)01 Jul 2026 - 26 Jul 2026From$401Seen: 14 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)15 May 2026 - 19 May 2026From$409Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)11 May 2026 - 16 May 2026From$409Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)15 Oct 2026 - 19 Oct 2026From$224Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)03 May 2026 - 06 May 2026From$234Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)11 Oct 2026 - 17 Oct 2026From$408Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)13 Jul 2026 - 16 Aug 2026From$408Seen: 8 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)17 Jun 2026 - 17 Jun 2026From$222Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)05 May 2026 - 12 May 2026From$222Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)16 Jun 2026 - 16 Jun 2026From$341Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)17 Jun 2026 - 17 Jun 2026From$341Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)08 Apr 2026 - 08 Apr 2026From$286Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)11 Apr 2026 - 15 Apr 2026From$321Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.