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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
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Oranjestad, St. Eustatius (EUX)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, Feb 02, 2026 - Mon, Feb 16, 2026 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Jul 17, 2025 - Sun, Jul 20, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Aug 11, 2025 - Mon, Aug 18, 2025 | From $398 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Jun 27, 2025 - Sun, Jun 29, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Wed, May 21, 2025 - Wed, May 21, 2025 | From $130 Seen: 4 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, May 20, 2025 - Tue, May 20, 2025 | From $130 Seen: 19 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jun 20, 2025 - Sun, Jun 22, 2025 | From $398 Seen: 22 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Oct 15, 2025 - Sat, Oct 18, 2025 | From $398 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, May 17, 2025 - Sat, May 17, 2025 | From $269 Seen: 14 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, May 23, 2025 - Sat, May 24, 2025 | From $269 Seen: 12 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, May 25, 2025 - Sun, May 25, 2025 | From $133 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Tue, May 20, 2025 - Tue, May 20, 2025 | From $133 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Sep 21, 2025 - Sun, Sep 28, 2025 | From $260 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Mon, Dec 01, 2025 - Sat, Dec 06, 2025 | From $260 Seen: 21 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, May 23, 2025 - Mon, May 26, 2025 | From $249 Seen: 17 hrs ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 28, 2025 - Tue, Sep 02, 2025 | From $367 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jul 04, 2025 - Sun, Jul 06, 2025 | From $367 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jun 13, 2025 - Mon, Jun 16, 2025 | From $249 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Tue, May 27, 2025 - Sat, Jun 07, 2025 | From $356 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sat, Oct 11, 2025 - Sat, Oct 25, 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)Mon, Feb 02, 2026 - Mon, Feb 16, 2026From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Jul 17, 2025 - Sun, Jul 20, 2025From$190Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Aug 11, 2025 - Mon, Aug 18, 2025From$398Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Fri, Jun 27, 2025 - Sun, Jun 29, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Wed, May 21, 2025 - Wed, May 21, 2025From$130Seen: 4 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Tue, May 20, 2025 - Tue, May 20, 2025From$130Seen: 19 hrs agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Fri, Jun 20, 2025 - Sun, Jun 22, 2025From$398Seen: 22 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Wed, Oct 15, 2025 - Sat, Oct 18, 2025From$398Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Sat, May 17, 2025 - Sat, May 17, 2025From$269Seen: 14 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Fri, May 23, 2025 - Sat, May 24, 2025From$269Seen: 12 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sun, May 25, 2025 - Sun, May 25, 2025From$133Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Tue, May 20, 2025 - Tue, May 20, 2025From$133Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Sun, Sep 21, 2025 - Sun, Sep 28, 2025From$260Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, Dec 01, 2025 - Sat, Dec 06, 2025From$260Seen: 21 hrs agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Fri, May 23, 2025 - Mon, May 26, 2025From$249Seen: 17 hrs agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Thu, Aug 28, 2025 - Tue, Sep 02, 2025From$367Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Fri, Jul 04, 2025 - Sun, Jul 06, 2025From$367Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Fri, Jun 13, 2025 - Mon, Jun 16, 2025From$249Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Tue, May 27, 2025 - Sat, Jun 07, 2025From$356Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Sat, Oct 11, 2025 - Sat, Oct 25, 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
- Bridgetown, Barbados - Willemstad, Curacao
- Bridgetown, Barbados - Philipsburg, Sint Maarten
- Bridgetown, Barbados - Oranjestad, St. Eustatius
- Bridgetown, Barbados - Kralendijk, Bonaire
- Bridgetown, Barbados - Basseterre, Saint Kitts
- Bridgetown, Barbados - Marigot, Dominica
- Bridgetown, Barbados - St. John's, Antigua
- Bridgetown, Barbados - Oranjestad, Aruba
- Bridgetown, Barbados - Road Town, Tortola
- Bridgetown, Barbados - Gustavia, Saint Barthélemy
- Bridgetown, Barbados - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Willemstad, Curacao - Oranjestad, St. Eustatius
- Willemstad, Curacao - Kralendijk, Bonaire
- Willemstad, Curacao - Basseterre, Saint Kitts