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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
Oranjestad, St. Eustatius (EUX)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)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)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)*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, Jul 10, 2025 - Thu, Jul 24, 2025 | From $184 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Dec 20, 2025 - Fri, Dec 26, 2025 | From $184 Seen: 2 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sat, Jun 28, 2025 - Sat, Jun 28, 2025 | From $167 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Tue, Jul 08, 2025 - Tue, Jul 08, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 15, 2025 - Sat, Sep 06, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Dec 03, 2025 - Mon, Dec 29, 2025 | From $397 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Mar 15, 2026 - Sun, Mar 22, 2026 | From $250 Seen: 20 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sat, Nov 22, 2025 - Sat, Nov 29, 2025 | From $250 Seen: 18 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jun 29, 2025 - Fri, Jul 11, 2025 | From $263 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Sep 07, 2025 - Tue, Sep 09, 2025 | From $397 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Fri, Jun 27, 2025 - Fri, Jun 27, 2025 | From $167 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 24, 2025 - Thu, Oct 02, 2025 | From $263 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Oct 04, 2025 - Wed, Oct 08, 2025 | From $397 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Sep 15, 2025 - Mon, Sep 22, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Jul 08, 2025 - Tue, Jul 08, 2025 | From $167 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Jul 24, 2025 - Mon, Jul 28, 2025 | From $396 Seen: 21 hrs ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 10, 2025 - Mon, Oct 13, 2025 | From $223 Seen: 3 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Sun, Feb 15, 2026 - Fri, Feb 20, 2026 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jan 16, 2026 - Sun, Jan 18, 2026 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Jul 04, 2025 - Fri, Jul 11, 2025 | From $396 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, Jul 10, 2025 - Thu, Jul 24, 2025From$184Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Dec 20, 2025 - Fri, Dec 26, 2025From$184Seen: 2 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sat, Jun 28, 2025 - Sat, Jun 28, 2025From$167Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Tue, Jul 08, 2025 - Tue, Jul 08, 2025From$167Seen: 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
- Oranjestad, Aruba - Willemstad, Curacao
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- The Bottom, Saba - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola