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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
Basseterre, Saint Kitts (SKB)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)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Marigot, Dominica (DOM)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 | Wed, Mar 11, 2026 - Tue, Mar 17, 2026 | From $185 Seen: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Aug 09, 2025 - Fri, Aug 15, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sat, Jan 24, 2026 - Tue, Jan 27, 2026 | From $283 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Fri, Sep 05, 2025 - Mon, Sep 08, 2025 | From $283 Seen: 11 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Aug 24, 2025 - Sat, Aug 30, 2025 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Aug 04, 2025 - Mon, Aug 25, 2025 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Sep 10, 2025 - Fri, Sep 12, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Sep 15, 2025 - Sun, Sep 21, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Wed, Aug 13, 2025 - Wed, Aug 13, 2025 | From $167 Seen: 7 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Aug 12, 2025 - Tue, Aug 12, 2025 | From $167 Seen: 3 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Dec 23, 2025 - Sat, Dec 27, 2025 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Aug 14, 2025 - Sun, Aug 17, 2025 | From $238 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Nov 02, 2025 - Tue, Nov 04, 2025 | From $250 Seen: 7 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Thu, Nov 20, 2025 - Mon, Nov 24, 2025 | From $250 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Sep 01, 2025 - Mon, Sep 08, 2025 | From $299 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Aug 22, 2025 - Thu, Aug 28, 2025 | From $299 Seen: 11 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Oct 12, 2025 - Sat, Oct 18, 2025 | From $365 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Nov 13, 2025 - Sun, Nov 16, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Fri, Aug 08, 2025 - Fri, Aug 08, 2025 | From $167 Seen: 12 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Thu, Aug 07, 2025 - Thu, Aug 07, 2025 | From $207 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)Wed, Mar 11, 2026 - Tue, Mar 17, 2026From$185Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Aug 09, 2025 - Fri, Aug 15, 2025From$185Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Sat, Jan 24, 2026 - Tue, Jan 27, 2026From$283Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Fri, Sep 05, 2025 - Mon, Sep 08, 2025From$283Seen: 11 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 - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Oranjestad, Aruba
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Marigot, Dominica - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten
- Castries, Saint Lucia - Philipsburg, Sint Maarten