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)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)*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 | 106, 04, 2026 - 110, 04, 2026 | From $269 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | 303, 10, 2025 - 310, 11, 2025 | From $269 Seen: 1 day 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 | 325, 11, 2025 - 328, 11, 2025 | From $282 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 313, 11, 2025 - 45, 02, 2026 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | 23, 01, 2026 - 24, 01, 2026 | From $397 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 314, 11, 2025 - 320, 11, 2025 | From $381 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | 332, 11, 2025 - 334, 11, 2025 | From $381 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 302, 10, 2025 - 302, 10, 2025 | From $216 Seen: 13 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | 296, 10, 2025 - 296, 10, 2025 | From $216 Seen: 38 minutes ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 122, 05, 2026 - 130, 05, 2026 | From $256 Seen: 13 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | 20, 01, 2026 - 26, 01, 2026 | From $266 Seen: 17 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 78, 03, 2026 - 81, 03, 2026 | From $246 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | 346, 12, 2025 - 353, 12, 2025 | From $256 Seen: 13 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 42, 02, 2026 - 46, 02, 2026 | From $282 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | 23, 01, 2026 - 26, 01, 2026 | From $282 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 330, 11, 2025 - 332, 11, 2025 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | 296, 10, 2025 - 299, 10, 2025 | From $226 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 69, 03, 2026 - 77, 03, 2026 | From $364 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | 79, 03, 2026 - 89, 03, 2026 | From $364 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.
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)106, 04, 2026 - 110, 04, 2026From$269Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)303, 10, 2025 - 310, 11, 2025From$269Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)359, 12, 2025 - 362, 12, 2026From$282Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)325, 11, 2025 - 328, 11, 2025From$282Seen: 1 day agoRound-trip
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.