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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)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)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)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)*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 | Wed, Jul 30, 2025 - Sun, Aug 03, 2025 | From $263 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Jan 24, 2026 - Sat, Jan 31, 2026 | From $263 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Thu, Aug 21, 2025 - Fri, Aug 29, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 15, 2025 - Fri, Aug 22, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Oct 24, 2025 - Mon, Oct 27, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Tue, Jul 01, 2025 - Sat, Jul 05, 2025 | From $396 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 23, 2025 - Mon, Jun 23, 2025 | From $263 Seen: 9 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 13, 2025 - Mon, Jul 14, 2025 | From $273 Seen: 2 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Dec 22, 2025 - Mon, Dec 22, 2025 | From $167 Seen: 8 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 18, 2025 - Mon, Sep 22, 2025 | From $337 Seen: 4 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Dec 24, 2025 - Sun, Dec 28, 2025 | From $397 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 25, 2025 - Fri, Oct 03, 2025 | From $397 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Aug 17, 2025 - Sat, Aug 23, 2025 | From $337 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Oct 23, 2025 - Mon, Oct 27, 2025 | From $238 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Thu, Jan 01, 2026 - Fri, Jan 02, 2026 | From $337 Seen: 4 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jan 02, 2026 - Mon, Jan 05, 2026 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Thu, Jun 26, 2025 - Thu, Jun 26, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Wed, Jun 25, 2025 - Wed, Jun 25, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Tue, Dec 23, 2025 - Sun, Dec 28, 2025 | From $337 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Jun 26, 2025 - Thu, Jun 26, 2025 | From $167 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)Wed, Jul 30, 2025 - Sun, Aug 03, 2025From$263Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Jan 24, 2026 - Sat, Jan 31, 2026From$263Seen: 16 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Thu, Aug 21, 2025 - Fri, Aug 29, 2025From$397Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Fri, Aug 15, 2025 - Fri, Aug 22, 2025From$397Seen: 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 - Marigot, Dominica
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Oranjestad, Aruba - Willemstad, Curacao
- St. John's, Antigua - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola