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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
The Bottom, Saba (SAB)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Willemstad, Curacao (CUR)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
Road Town, Tortola (EIS)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)*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 | Tue, Jul 22, 2025 - Tue, Jul 29, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jul 02, 2025 - Fri, Jul 04, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Thu, Aug 14, 2025 - Tue, Aug 19, 2025 | From $397 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Sep 06, 2025 - Fri, Sep 19, 2025 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Jun 30, 2025 - Mon, Jun 30, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Aug 25, 2025 - Mon, Aug 25, 2025 | From $167 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jun 29, 2025 - Sun, Jun 29, 2025 | From $195 Seen: 11 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 30, 2025 - Tue, Jul 01, 2025 | From $263 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Aug 12, 2025 - Sun, Sep 21, 2025 | From $263 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Fri, Sep 19, 2025 - Mon, Sep 22, 2025 | From $337 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Dec 07, 2025 - Fri, Dec 12, 2025 | From $397 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Aug 18, 2025 - Mon, Aug 25, 2025 | From $397 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Aug 25, 2025 - Mon, Aug 25, 2025 | From $203 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Oct 31, 2025 - Fri, Nov 14, 2025 | From $396 Seen: 49 minutes ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Aug 22, 2025 - Thu, Aug 28, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sun, Feb 08, 2026 - Sat, Feb 14, 2026 | From $337 Seen: 15 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Sat, Aug 02, 2025 - Mon, Aug 11, 2025 | From $238 Seen: 18 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jul 25, 2025 - Mon, Aug 11, 2025 | From $238 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Aug 17, 2025 - Sun, Aug 31, 2025 | From $224 Seen: 1 day ago |
| The Bottom, Saba (SAB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 05, 2025 - Tue, Jul 08, 2025 | From $224 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)Tue, Jul 22, 2025 - Tue, Jul 29, 2025From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jul 02, 2025 - Fri, Jul 04, 2025From$185Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Thu, Aug 14, 2025 - Tue, Aug 19, 2025From$397Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Sep 06, 2025 - Fri, Sep 19, 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Road Town, Tortola
- Road Town, Tortola - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao