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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)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)*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 | Sat, Aug 02, 2025 - Fri, Aug 15, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Jul 10, 2025 - Thu, Jul 10, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sun, Feb 08, 2026 - Sun, Feb 22, 2026 | From $396 Seen: 2 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sun, Oct 05, 2025 - Sat, Oct 11, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Aug 18, 2025 - Fri, Aug 22, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sun, Mar 01, 2026 - Wed, Mar 04, 2026 | From $337 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Wed, Nov 05, 2025 - Tue, Nov 11, 2025 | From $337 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Sep 09, 2025 - Thu, Sep 11, 2025 | From $397 Seen: 15 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Mar 08, 2026 - Sat, Mar 21, 2026 | From $397 Seen: 19 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Aug 01, 2025 - Fri, Aug 22, 2025 | From $263 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 12, 2025 - Sun, Aug 17, 2025 | From $273 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Dec 26, 2025 - Fri, Jan 30, 2026 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Aug 15, 2025 - Sun, Aug 17, 2025 | From $238 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Dec 21, 2025 - Sat, Dec 27, 2025 | From $396 Seen: 6 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sat, Aug 23, 2025 - Sat, Aug 30, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 20, 2025 - Wed, Aug 20, 2025 | From $396 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Nov 09, 2025 - Wed, Nov 12, 2025 | From $250 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Feb 16, 2026 - Wed, Feb 18, 2026 | From $224 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Wed, Sep 03, 2025 - Sun, Sep 07, 2025 | From $224 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, Jul 06, 2025 - Sun, Jul 06, 2025 | From $204 Seen: 23 hrs 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)Sat, Aug 02, 2025 - Fri, Aug 15, 2025From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Jul 10, 2025 - Thu, Jul 10, 2025From$185Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Sun, Feb 08, 2026 - Sun, Feb 22, 2026From$396Seen: 2 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sun, Oct 05, 2025 - Sat, Oct 11, 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Marigot, Dominica - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Philipsburg, Sint Maarten - Road Town, Tortola
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, Aruba
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Castries, Saint Lucia - Philipsburg, Sint Maarten