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Travel Throughout the Caribbean with Winair, with these best one way flight deals
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)*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) | Willemstad, Curacao (CUR) | Round-trip | Sun, Aug 17, 2025 - Fri, Aug 29, 2025 | From $397 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Oct 13, 2025 - Mon, Oct 20, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jul 09, 2025 - Wed, Jul 09, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Nov 15, 2025 - Tue, Nov 25, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sat, Feb 14, 2026 - Fri, Feb 20, 2026 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sat, Jul 05, 2025 - Sat, Jul 05, 2025 | From $211 Seen: 15 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Nov 12, 2025 - Wed, Nov 19, 2025 | From $397 Seen: 12 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jul 04, 2025 - Wed, Jul 09, 2025 | From $263 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sat, Oct 04, 2025 - Sun, Oct 12, 2025 | From $396 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Dec 24, 2025 - Mon, Dec 29, 2025 | From $337 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Jul 07, 2025 - Mon, Jul 07, 2025 | From $167 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 24, 2025 - Fri, Oct 24, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sat, Jul 05, 2025 - Sat, Jul 05, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Jul 08, 2025 - Tue, Jul 08, 2025 | From $197 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Dec 19, 2025 - Mon, Dec 22, 2025 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Dec 19, 2025 - Tue, Dec 23, 2025 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Thu, Feb 26, 2026 - Tue, Mar 03, 2026 | From $337 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Thu, Aug 07, 2025 - Fri, Aug 22, 2025 | From $337 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | Fri, Jul 25, 2025 - Sun, Jul 27, 2025 | From $367 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | Wed, Jul 09, 2025 - Fri, Jul 11, 2025 | From $367 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
Willemstad, Curacao (CUR)Sun, Aug 17, 2025 - Fri, Aug 29, 2025From$397Seen: 4 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Oct 13, 2025 - Mon, Oct 20, 2025From$397Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jul 09, 2025 - Wed, Jul 09, 2025From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Nov 15, 2025 - Tue, Nov 25, 2025From$185Seen: 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - The Bottom, Saba
- Philipsburg, Sint Maarten - St. John's, Antigua
- Philipsburg, Sint Maarten - Road Town, Tortola
- Oranjestad, Aruba - Willemstad, Curacao
- Marigot, Dominica - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten