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Travel Throughout the Caribbean with Winair, with these best one way flight deals
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Castries, Saint Lucia (SLU)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) | Willemstad, Curacao (CUR) | Round-trip | Thu, Sep 04, 2025 - Mon, Sep 08, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sun, Oct 05, 2025 - Fri, Oct 10, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jul 23, 2025 - Wed, Jul 23, 2025 | From $185 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Feb 25, 2026 - Sun, Mar 01, 2026 | From $185 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Sep 21, 2025 - Sun, Sep 21, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sat, Jul 26, 2025 - Sat, Jul 26, 2025 | From $167 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 21, 2025 - Tue, Aug 05, 2025 | From $263 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jan 26, 2026 - Fri, Feb 06, 2026 | From $263 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 31, 2025 - Mon, Nov 03, 2025 | From $365 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 03, 2025 - Fri, Oct 10, 2025 | From $365 Seen: 15 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Oct 30, 2025 - Mon, Nov 03, 2025 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Oct 03, 2025 - Fri, Oct 10, 2025 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Tue, Dec 16, 2025 - Sun, Dec 21, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sun, Dec 14, 2025 - Thu, Dec 18, 2025 | From $396 Seen: 17 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 27, 2025 - Sun, Aug 03, 2025 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Nov 21, 2025 - Mon, Nov 24, 2025 | From $283 Seen: 17 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Fri, Sep 19, 2025 - Sun, Sep 21, 2025 | From $250 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Tue, Sep 02, 2025 - Tue, Sep 09, 2025 | From $250 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Aug 02, 2025 - Sat, Aug 16, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 20, 2025 - Tue, Sep 02, 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
Willemstad, Curacao (CUR)Thu, Sep 04, 2025 - Mon, Sep 08, 2025From$365Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sun, Oct 05, 2025 - Fri, Oct 10, 2025From$365Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jul 23, 2025 - Wed, Jul 23, 2025From$185Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Feb 25, 2026 - Sun, Mar 01, 2026From$185Seen: 3 hrs 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 - The Bottom, Saba
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Marigot, Dominica
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Marigot, Dominica - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Castries, Saint Lucia - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Road Town, Tortola - Philipsburg, Sint Maarten