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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)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)The Bottom, Saba (SAB)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)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 | Thu, Jul 10, 2025 - Tue, Jul 15, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Jun 05, 2025 - Sat, Jun 07, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Jun 18, 2025 - Wed, Jul 09, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Jul 14, 2025 - Fri, Jul 18, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Aug 22, 2025 - Sun, Sep 07, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Mon, Jun 30, 2025 - Sat, Jul 05, 2025 | From $356 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 |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Dec 27, 2025 - Sat, Jan 10, 2026 | From $269 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, Feb 25, 2026 - Wed, Mar 11, 2026 | From $396 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, May 30, 2025 - Mon, Jun 02, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 10, 2025 - Wed, Oct 15, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Aug 01, 2025 - Mon, Aug 11, 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: 7 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Mon, Oct 20, 2025 - Mon, Oct 20, 2025 | From $260 Seen: 3 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Aug 09, 2025 - Thu, Aug 21, 2025 | From $356 Seen: 5 hrs ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Jun 12, 2025 - Sun, Jun 15, 2025 | From $367 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Oct 07, 2025 - Sun, Oct 12, 2025 | From $249 Seen: 13 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jun 08, 2025 - Sun, Jun 08, 2025 | From $130 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Jun 09, 2025 - Mon, Jun 09, 2025 | From $159 Seen: 4 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Nov 11, 2025 - Sun, Nov 16, 2025 | From $356 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)Thu, Jul 10, 2025 - Tue, Jul 15, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Jun 05, 2025 - Sat, Jun 07, 2025From$190Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Wed, Jun 18, 2025 - Wed, Jul 09, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Jul 14, 2025 - Fri, Jul 18, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Fri, Aug 22, 2025 - Sun, Sep 07, 2025From$396Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Mon, Jun 30, 2025 - Sat, Jul 05, 2025From$356Seen: 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-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Sat, Dec 27, 2025 - Sat, Jan 10, 2026From$269Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Wed, Feb 25, 2026 - Wed, Mar 11, 2026From$396Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Fri, May 30, 2025 - Mon, Jun 02, 2025From$249Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Fri, Oct 10, 2025 - Wed, Oct 15, 2025From$398Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Fri, Aug 01, 2025 - Mon, Aug 11, 2025From$398Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, Feb 09, 2026 - Tue, Feb 17, 2026From$260Seen: 7 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, Oct 20, 2025 - Mon, Oct 20, 2025From$260Seen: 3 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sat, Aug 09, 2025 - Thu, Aug 21, 2025From$356Seen: 5 hrs agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Thu, Jun 12, 2025 - Sun, Jun 15, 2025From$367Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Tue, Oct 07, 2025 - Sun, Oct 12, 2025From$249Seen: 13 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Sun, Jun 08, 2025 - Sun, Jun 08, 2025From$130Seen: 4 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Mon, Jun 09, 2025 - Mon, Jun 09, 2025From$159Seen: 4 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Tue, Nov 11, 2025 - Sun, Nov 16, 2025From$356Seen: 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
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Philipsburg, Sint Maarten - Marigot, Dominica
- Oranjestad, Aruba - Willemstad, Curacao
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - The Bottom, Saba
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Road Town, Tortola - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - St. John's, Antigua