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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)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)The Bottom, Saba (SAB)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) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Mar 12, 2026 - Thu, Mar 12, 2026 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Fri, Aug 01, 2025 - Fri, Aug 08, 2025 | From $185 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Sep 14, 2025 - Sat, Sep 20, 2025 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Sep 10, 2025 - Fri, Sep 19, 2025 | From $365 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 21, 2025 - Mon, Aug 25, 2025 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sun, Sep 28, 2025 - Mon, Oct 06, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Jul 24, 2025 - Thu, Jul 24, 2025 | From $167 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Dec 02, 2025 - Tue, Dec 02, 2025 | From $167 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Mar 17, 2026 - Sun, Mar 22, 2026 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Sun, Oct 12, 2025 - Sun, Oct 12, 2025 | From $238 Seen: 12 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 03, 2025 - Sat, Oct 11, 2025 | From $365 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Aug 06, 2025 - Wed, Aug 20, 2025 | From $347 Seen: 2 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Aug 30, 2025 - Fri, Sep 05, 2025 | From $299 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Thu, Nov 20, 2025 - Thu, Nov 20, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Thu, Jul 24, 2025 - Mon, Jul 28, 2025 | From $236 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Oct 24, 2025 - Tue, Oct 28, 2025 | From $299 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Sep 12, 2025 - Fri, Sep 26, 2025 | From $299 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Sat, Jul 26, 2025 | From $224 Seen: 2 hrs ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 28, 2025 - Mon, Jul 28, 2025 | From $224 Seen: 3 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jul 30, 2025 - Wed, Jul 30, 2025 | From $263 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)Thu, Mar 12, 2026 - Thu, Mar 12, 2026From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Fri, Aug 01, 2025 - Fri, Aug 08, 2025From$185Seen: 1 day agoRound-trip
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sun, Sep 14, 2025 - Sat, Sep 20, 2025From$283Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Wed, Sep 10, 2025 - Fri, Sep 19, 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
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - The Bottom, Saba
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Marigot, Dominica - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola
- St. John's, Antigua - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts