Find The Best Flight Deals from $65
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Travel Throughout the Caribbean with Winair, with these best one way flight deals
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)*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 | 89, 03, 2026 - 89, 03, 2026 | From $269 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 333, 11, 2025 - 333, 11, 2025 | From $269 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 296, 10, 2025 - 306, 11, 2025 | From $256 Seen: 3 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 155, 06, 2026 - 155, 06, 2026 | From $256 Seen: 3 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 330, 11, 2025 - 337, 12, 2025 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 360, 12, 2025 - 364, 12, 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 35, 02, 2026 - 38, 02, 2026 | From $216 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 314, 11, 2025 - 318, 11, 2025 | From $381 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 347, 12, 2025 - 351, 12, 2025 | From $282 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 227, 08, 2026 - 231, 08, 2026 | From $282 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 263, 09, 2026 - 269, 09, 2026 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 317, 11, 2025 - 323, 11, 2025 | From $365 Seen: 2 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 311, 11, 2025 - 316, 11, 2025 | From $381 Seen: 1 hour ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 74, 03, 2026 - 90, 03, 2026 | From $364 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 88, 03, 2026 - 89, 03, 2026 | From $364 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 96, 04, 2026 - 98, 04, 2026 | From $282 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | 336, 12, 2025 - 15, 01, 2026 | From $282 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 44, 02, 2026 - 55, 02, 2026 | From $349 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | 319, 11, 2025 - 327, 11, 2025 | From $349 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 139, 05, 2026 - 145, 05, 2026 | From $226 Seen: 6 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.
Current Flight Routes of Winair
Status | From | To | Date(s) | Actions |
|---|---|---|---|---|
Active | Antigua (ANU) | Sint Maarten (SXM) | Ongoing | |
Active | Antigua (ANU) | Tortola (EIS) | Ongoing | |
Active | Antigua (ANU) | Dominica (DOM) | Ongoing | |
Active | Aruba (AUA) | Sint Maarten (SXM) | Ongoing | |
Active | Aruba (AUA) | Curacao (CUR) | Ongoing | |
Active | Bonaire (BON) | Sint Maarten (SXM) | Ongoing | |
Active | Bonaire (BON) | Curacao (CUR) | Ongoing | |
Active | Curacao (CUR) | Bonaire (BON) | Ongoing | |
Active | Curacao (CUR) | Sint Maarten (SXM) | Ongoing | |
Active | Curacao (CUR) | Aruba (AUA) | Ongoing |
Most Popular Round trip Flight Deals with Winair
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)89, 03, 2026 - 89, 03, 2026From$269Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)333, 11, 2025 - 333, 11, 2025From$269Seen: 1 day agoRound-trip
Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)296, 10, 2025 - 306, 11, 2025From$256Seen: 3 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)155, 06, 2026 - 155, 06, 2026From$256Seen: 3 hrs agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.