Find The Best Flight Deals from $73
Travel Throughout the Caribbean with Winair, with these best one way flight deals
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)*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
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 143, 05, 2026 - 150, 05, 2026 | From $269 Seen: 10 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 326, 11, 2025 - 336, 12, 2025 | From $269 Seen: 17 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 339, 12, 2025 - 346, 12, 2025 | From $285 Seen: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 359, 12, 2025 - 362, 12, 2026 | From $282 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 356, 12, 2025 - 02, 01, 2026 | From $282 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 305, 11, 2025 - 308, 11, 2025 | From $399 Seen: 13 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 283, 10, 2025 - 312, 11, 2025 | From $269 Seen: 5 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 287, 10, 2025 - 290, 10, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 358, 12, 2025 - 02, 01, 2026 | From $397 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 331, 11, 2025 - 334, 11, 2025 | From $226 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 272, 09, 2025 - 280, 10, 2025 | From $231 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 346, 12, 2025 - 349, 12, 2025 | From $341 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 288, 10, 2025 - 309, 11, 2025 | From $399 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 51, 02, 2026 - 58, 02, 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 276, 10, 2025 - 276, 10, 2025 | From $216 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 03, 01, 2026 - 08, 01, 2026 | From $282 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 189, 07, 2026 - 189, 07, 2026 | From $282 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | 276, 10, 2025 - 278, 10, 2025 | From $269 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | 355, 12, 2025 - 358, 12, 2025 | From $226 Seen: 11 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 139, 05, 2026 - 142, 05, 2026 | From $256 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
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)143, 05, 2026 - 150, 05, 2026From$269Seen: 10 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)326, 11, 2025 - 336, 12, 2025From$269Seen: 17 hrs agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)339, 12, 2025 - 346, 12, 2025From$285Seen: 15 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)359, 12, 2025 - 362, 12, 2026From$282Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.
Popular flights from Winair
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - The Bottom, Saba
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Oranjestad, Aruba - Willemstad, Curacao
- Philipsburg, Sint Maarten - Road Town, Tortola
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, Aruba
- St. John's, Antigua - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Bridgetown, Barbados