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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Basseterre, Saint Kitts (SKB)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
Basseterre, Saint Kitts (SKB)Road Town, Tortola (EIS)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 | Sat, May 31, 2025 - Wed, Jun 11, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Jan 12, 2026 - Mon, Jan 19, 2026 | From $190 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 02, 2025 - Wed, Jun 04, 2025 | From $269 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Sep 13, 2025 - Tue, Sep 16, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Sep 12, 2025 - Tue, Sep 16, 2025 | From $398 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 02, 2025 - Thu, Jun 05, 2025 | From $269 Seen: 13 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Jun 03, 2025 - Tue, Jun 03, 2025 | From $130 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, May 29, 2025 - Thu, May 29, 2025 | From $130 Seen: 4 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Aug 15, 2025 - Sun, Aug 24, 2025 | From $398 Seen: 18 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Wed, Sep 03, 2025 - Wed, Sep 03, 2025 | From $260 Seen: 11 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Aug 31, 2025 - Sat, Sep 06, 2025 | From $260 Seen: 8 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Sep 03, 2025 - Mon, Sep 08, 2025 | From $249 Seen: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Tue, Jun 03, 2025 - Tue, Jun 03, 2025 | From $170 Seen: 16 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 30, 2025 - Fri, Aug 22, 2025 | From $330 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, Sep 10, 2025 - Mon, Sep 22, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sat, Jun 14, 2025 - Mon, Jun 16, 2025 | From $396 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Feb 09, 2026 - Thu, Feb 12, 2026 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Jul 10, 2025 - Thu, Jul 24, 2025 | From $249 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Nov 21, 2025 - Fri, Nov 28, 2025 | From $356 Seen: 18 hrs ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Jun 03, 2025 - Fri, Jun 06, 2025 | From $367 Seen: 12 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
Gustavia, Saint Barthélemy (SBH)Sat, May 31, 2025 - Wed, Jun 11, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Mon, Jan 12, 2026 - Mon, Jan 19, 2026From$190Seen: 1 day agoRound-trip
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Mon, Jun 02, 2025 - Wed, Jun 04, 2025From$269Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Sep 13, 2025 - Tue, Sep 16, 2025From$398Seen: 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
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten
- St. John's, Antigua - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Castries, Saint Lucia