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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)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 | Mon, Aug 04, 2025 - Sat, Aug 09, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Fri, Jan 02, 2026 - Fri, Jan 02, 2026 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Tue, Dec 23, 2025 - Fri, Jan 02, 2026 | From $398 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 17, 2025 - Tue, Oct 28, 2025 | From $269 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Sep 22, 2025 - Sun, Sep 28, 2025 | From $398 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Aug 08, 2025 - Thu, Aug 14, 2025 | From $396 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) | Marigot, Dominica (DOM) | Round-trip | Fri, Jul 04, 2025 - Fri, Jul 18, 2025 | From $396 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 30, 2025 - Fri, Aug 22, 2025 | From $330 Seen: 4 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Oct 20, 2025 - Mon, Oct 27, 2025 | From $398 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Mon, Feb 09, 2026 - Tue, Feb 17, 2026 | From $260 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Mon, Oct 20, 2025 - Mon, Oct 20, 2025 | From $260 Seen: 20 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Aug 09, 2025 - Thu, Aug 21, 2025 | From $356 Seen: 22 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jun 01, 2025 - Sun, Jun 01, 2025 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, Jun 01, 2025 - Sun, Jun 01, 2025 | From $133 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Oct 07, 2025 - Sun, Oct 12, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Oct 09, 2025 - Sun, Oct 12, 2025 | From $249 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jun 08, 2025 - Sun, Jun 08, 2025 | From $130 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Jun 09, 2025 - Mon, Jun 09, 2025 | From $159 Seen: 21 hrs ago |
| Oranjestad, St. Eustatius (EUX) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jun 28, 2025 - Tue, Jul 01, 2025 | From $238 Seen: 18 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)Mon, Aug 04, 2025 - Sat, Aug 09, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Fri, Jan 02, 2026 - Fri, Jan 02, 2026From$190Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Tue, Dec 23, 2025 - Fri, Jan 02, 2026From$398Seen: 1 day agoRound-trip
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Fri, Oct 17, 2025 - Tue, Oct 28, 2025From$269Seen: 17 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Sep 22, 2025 - Sun, Sep 28, 2025From$398Seen: 17 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Fri, Aug 08, 2025 - Thu, Aug 14, 2025From$396Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Mon, Jun 02, 2025 - Wed, Jun 04, 2025From$269Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Fri, Jul 04, 2025 - Fri, Jul 18, 2025From$396Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Mon, Jun 30, 2025 - Fri, Aug 22, 2025From$330Seen: 4 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Mon, Oct 20, 2025 - Mon, Oct 27, 2025From$398Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, Feb 09, 2026 - Tue, Feb 17, 2026From$260Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, Oct 20, 2025 - Mon, Oct 20, 2025From$260Seen: 20 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sat, Aug 09, 2025 - Thu, Aug 21, 2025From$356Seen: 22 hrs agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Sun, Jun 01, 2025 - Sun, Jun 01, 2025From$238Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sun, Jun 01, 2025 - Sun, Jun 01, 2025From$133Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Tue, Oct 07, 2025 - Sun, Oct 12, 2025From$249Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Thu, Oct 09, 2025 - Sun, Oct 12, 2025From$249Seen: 23 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Sun, Jun 08, 2025 - Sun, Jun 08, 2025From$130Seen: 21 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Mon, Jun 09, 2025 - Mon, Jun 09, 2025From$159Seen: 21 hrs agoRound-tripOranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Sat, Jun 28, 2025 - Tue, Jul 01, 2025From$238Seen: 18 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
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Philipsburg, Sint Maarten - The Bottom, Saba
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Oranjestad, Aruba - Willemstad, Curacao
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- The Bottom, Saba - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Road Town, Tortola - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten