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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)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Oranjestad, St. Eustatius (EUX)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 | Tue, Aug 05, 2025 - Sat, Aug 09, 2025 | From $184 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Nov 26, 2025 - Sun, Nov 30, 2025 | From $184 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Sep 03, 2025 - Sat, Sep 06, 2025 | From $365 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Thu, Oct 16, 2025 - Tue, Oct 21, 2025 | From $365 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Aug 29, 2025 - Mon, Sep 01, 2025 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Dec 15, 2025 - Fri, Dec 19, 2025 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Wed, Aug 13, 2025 - Wed, Aug 13, 2025 | From $167 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Sep 13, 2025 - Wed, Sep 17, 2025 | From $365 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 14, 2025 - Mon, Aug 18, 2025 | From $263 Seen: 12 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Oct 12, 2025 - Sat, Oct 25, 2025 | From $263 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Tue, Aug 26, 2025 - Fri, Aug 29, 2025 | From $283 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sat, Aug 09, 2025 - Sat, Aug 09, 2025 | From $167 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sun, Aug 24, 2025 - Tue, Aug 26, 2025 | From $283 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Tue, Oct 14, 2025 - Sun, Oct 19, 2025 | From $250 Seen: 22 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Fri, Dec 26, 2025 - Fri, Jan 09, 2026 | From $250 Seen: 18 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Aug 20, 2025 - Mon, Aug 25, 2025 | From $299 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Sep 22, 2025 - Thu, Sep 25, 2025 | From $365 Seen: 2 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Aug 20, 2025 - Thu, Aug 28, 2025 | From $299 Seen: 23 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Aug 05, 2025 - Mon, Aug 11, 2025 | From $236 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Dec 20, 2025 - Sun, Jan 04, 2026 | From $236 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)Tue, Aug 05, 2025 - Sat, Aug 09, 2025From$184Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Nov 26, 2025 - Sun, Nov 30, 2025From$184Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Wed, Sep 03, 2025 - Sat, Sep 06, 2025From$365Seen: 22 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Thu, Oct 16, 2025 - Tue, Oct 21, 2025From$365Seen: 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - The Bottom, Saba
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Kralendijk, Bonaire
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Gerald's
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten