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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)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)*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 12, 2025 - Tue, Aug 12, 2025 | From $185 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Aug 04, 2025 - Wed, Aug 13, 2025 | From $185 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Oct 03, 2025 - Fri, Oct 10, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Oct 01, 2025 - Tue, Oct 14, 2025 | From $365 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Mar 17, 2026 - Sat, Mar 28, 2026 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Aug 17, 2025 - Sun, Aug 24, 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: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Aug 12, 2025 - Tue, Aug 12, 2025 | From $167 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Oct 02, 2025 - Wed, Oct 08, 2025 | From $365 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 03, 2025 - Sat, Sep 06, 2025 | From $365 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 14, 2025 - Sun, Oct 05, 2025 | From $263 Seen: 12 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Nov 05, 2025 - Wed, Nov 05, 2025 | From $263 Seen: 14 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Sep 26, 2025 - Sun, Sep 28, 2025 | From $347 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Oct 19, 2025 - Fri, Oct 31, 2025 | From $347 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Aug 06, 2025 - Mon, Aug 11, 2025 | From $236 Seen: 1 day ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Nov 01, 2025 - Sat, Nov 22, 2025 | From $236 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Fri, Feb 27, 2026 - Tue, Mar 03, 2026 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Tue, Aug 12, 2025 - Tue, Aug 12, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, Aug 03, 2025 - Sun, Aug 03, 2025 | From $167 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Sep 26, 2025 - Wed, Oct 01, 2025 | From $299 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 12, 2025 - Tue, Aug 12, 2025From$185Seen: 21 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Mon, Aug 04, 2025 - Wed, Aug 13, 2025From$185Seen: 18 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Fri, Oct 03, 2025 - Fri, Oct 10, 2025From$365Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Wed, Oct 01, 2025 - Tue, Oct 14, 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 - The Bottom, Saba
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - St. John's, Antigua
- Oranjestad, Aruba - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao