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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)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)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) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 01, 2025 - Sun, Aug 10, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Jul 11, 2025 - Sat, Jul 19, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Aug 23, 2025 - Sat, Aug 23, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jun 18, 2025 - Wed, Jun 18, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Jun 17, 2025 - Tue, Jun 17, 2025 | From $130 Seen: 2 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 14, 2025 - Fri, Jul 18, 2025 | From $269 Seen: 17 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 14, 2025 - Mon, Jul 14, 2025 | From $269 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Jun 12, 2025 - Thu, Jun 12, 2025 | From $130 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Nov 11, 2025 - Tue, Nov 11, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Sep 09, 2025 - Fri, Sep 19, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Oct 09, 2025 - Mon, Oct 13, 2025 | From $398 Seen: 9 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jan 12, 2026 - Tue, Jan 20, 2026 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Wed, Mar 11, 2026 - Mon, Mar 16, 2026 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sat, Dec 27, 2025 - Wed, Jan 07, 2026 | From $356 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jul 30, 2025 - Wed, Aug 13, 2025 | From $356 Seen: 10 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jan 02, 2026 - Mon, Jan 05, 2026 | From $249 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Jun 09, 2025 - Mon, Jun 09, 2025 | From $170 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jun 28, 2025 - Wed, Aug 27, 2025 | From $386 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Dec 26, 2025 - Sat, Jan 03, 2026 | From $386 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, Sep 17, 2025 - Wed, Sep 24, 2025 | From $396 Seen: 22 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
Willemstad, Curacao (CUR)Fri, Aug 01, 2025 - Sun, Aug 10, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Fri, Jul 11, 2025 - Sat, Jul 19, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Aug 23, 2025 - Sat, Aug 23, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jun 18, 2025 - Wed, Jun 18, 2025From$190Seen: 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 - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - St. John's, Antigua
- Marigot, Dominica - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Oranjestad, Aruba - Willemstad, Curacao
- Road Town, Tortola - Philipsburg, Sint Maarten