Find The Best Flight Deals from $80
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: 16 Mar 2026
From
$163
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Depart: 09 Jan 2026
From
$137
Seen: 17 hrs ago
One-way
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Depart: 15 Jan 2026
From
$108
Seen: 7 hrs ago
One-way
Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Feb 2026
From
$184
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)Depart: 08 Jan 2026
From
$230
Seen: 1 day ago
One-way
St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Depart: 18 Jan 2026
From
$172
Seen: 1 day ago
One-way
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Depart: 02 Mar 2026
From
$152
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Depart: 21 Feb 2026
From
$220
Seen: 1 day ago
One-way
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Depart: 17 Jan 2026
From
$183
Seen: 1 day ago
One-way
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Depart: 25 Dec 2025
From
$129
Seen: 11 hrs ago
One-way
Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Depart: 28 Jan 2026
From
$85
Seen: 1 day ago
One-way
Charlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)Depart: 04 Mar 2026
From
$125
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 | 29 Jan 2026 - 02 Feb 2026 | From $270 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 24 Jan 2026 - 29 Jan 2026 | From $270 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 14 May 2026 - 24 May 2026 | From $270 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 30 Dec 2025 - 02 Jan 2026 | From $270 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 15 Apr 2026 - 18 Apr 2026 | From $217 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 23 May 2026 - 30 May 2026 | From $217 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 01 Feb 2026 - 08 Feb 2026 | From $335 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 25 Dec 2025 - 30 Dec 2025 | From $414 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | 24 Dec 2025 - 02 Jan 2026 | From $529 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 28 Nov 2026 - 05 Dec 2026 | From $414 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 22 Dec 2025 - 24 Dec 2025 | From $414 Seen: 11 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 09 Feb 2026 - 19 Feb 2026 | From $335 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 02 Apr 2026 - 06 Apr 2026 | From $409 Seen: 8 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03 Apr 2026 - 06 Apr 2026 | From $335 Seen: 5 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 24 Aug 2026 - 24 Aug 2026 | From $335 Seen: 2 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | 18 Apr 2026 - 26 Apr 2026 | From $390 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 12 Feb 2026 - 06 Mar 2026 | From $374 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 29 Jan 2026 - 01 Feb 2026 | From $217 Seen: 11 hrs ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | 05 Jan 2026 - 11 Jan 2026 | From $390 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 22 Dec 2025 - 23 Dec 2025 | From $217 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)29 Jan 2026 - 02 Feb 2026From$270Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)24 Jan 2026 - 29 Jan 2026From$270Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)14 May 2026 - 24 May 2026From$270Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)30 Dec 2025 - 02 Jan 2026From$270Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)15 Apr 2026 - 18 Apr 2026From$217Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)23 May 2026 - 30 May 2026From$217Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)01 Feb 2026 - 08 Feb 2026From$335Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)25 Dec 2025 - 30 Dec 2025From$414Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)24 Dec 2025 - 02 Jan 2026From$529Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)28 Nov 2026 - 05 Dec 2026From$414Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)22 Dec 2025 - 24 Dec 2025From$414Seen: 11 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)09 Feb 2026 - 19 Feb 2026From$335Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)02 Apr 2026 - 06 Apr 2026From$409Seen: 8 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)03 Apr 2026 - 06 Apr 2026From$335Seen: 5 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)24 Aug 2026 - 24 Aug 2026From$335Seen: 2 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)18 Apr 2026 - 26 Apr 2026From$390Seen: 16 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)12 Feb 2026 - 06 Mar 2026From$374Seen: 1 day agoRound-tripThe Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)29 Jan 2026 - 01 Feb 2026From$217Seen: 11 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)05 Jan 2026 - 11 Jan 2026From$390Seen: 1 day agoRound-tripThe Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)22 Dec 2025 - 23 Dec 2025From$217Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.