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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)St. John's, Antigua (ANU)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 | Sun, Nov 30, 2025 - Sun, Dec 07, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Nov 29, 2025 - Sat, Dec 06, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Tue, Jul 15, 2025 - Fri, Jul 25, 2025 | From $398 Seen: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Nov 15, 2025 - Sat, Nov 29, 2025 | From $398 Seen: 7 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, May 16, 2025 - Sat, May 17, 2025 | From $269 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Aug 27, 2025 - Sun, Aug 31, 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: 19 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Fri, Aug 08, 2025 - Fri, Aug 08, 2025 | From $157 Seen: 17 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Jul 31, 2025 - Mon, Aug 04, 2025 | From $279 Seen: 21 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Oct 15, 2025 - Sat, Oct 18, 2025 | From $398 Seen: 15 hrs ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jul 30, 2025 - Wed, Aug 06, 2025 | From $367 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, May 19, 2025 - Mon, May 19, 2025 | From $133 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, May 25, 2025 - Sun, May 25, 2025 | From $133 Seen: 17 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Thu, Sep 11, 2025 - Mon, Sep 15, 2025 | From $260 Seen: 18 hrs ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Aug 09, 2025 - Sat, Aug 23, 2025 | From $356 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 16, 2025 - Mon, Jun 16, 2025 | From $356 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 28, 2025 - Tue, Sep 02, 2025 | From $367 Seen: 6 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 17, 2025 - Sat, Sep 20, 2025 | From $386 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jun 06, 2025 - Sun, Jun 08, 2025 | From $386 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Mon, Jan 12, 2026 - Fri, Jan 23, 2026 | From $249 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)Sun, Nov 30, 2025 - Sun, Dec 07, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Nov 29, 2025 - Sat, Dec 06, 2025From$190Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Tue, Jul 15, 2025 - Fri, Jul 25, 2025From$398Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Nov 15, 2025 - Sat, Nov 29, 2025From$398Seen: 7 hrs agoRound-trip
Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Fri, May 16, 2025 - Sat, May 17, 2025From$269Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Wed, Aug 27, 2025 - Sun, Aug 31, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Wed, May 21, 2025 - Wed, May 21, 2025From$130Seen: 19 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Fri, Aug 08, 2025 - Fri, Aug 08, 2025From$157Seen: 17 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Thu, Jul 31, 2025 - Mon, Aug 04, 2025From$279Seen: 21 hrs agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Wed, Oct 15, 2025 - Sat, Oct 18, 2025From$398Seen: 15 hrs agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Wed, Jul 30, 2025 - Wed, Aug 06, 2025From$367Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Mon, May 19, 2025 - Mon, May 19, 2025From$133Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sun, May 25, 2025 - Sun, May 25, 2025From$133Seen: 17 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Thu, Sep 11, 2025 - Mon, Sep 15, 2025From$260Seen: 18 hrs agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sat, Aug 09, 2025 - Sat, Aug 23, 2025From$356Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Mon, Jun 16, 2025 - Mon, Jun 16, 2025From$356Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Thu, Aug 28, 2025 - Tue, Sep 02, 2025From$367Seen: 6 hrs agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Wed, Sep 17, 2025 - Sat, Sep 20, 2025From$386Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Fri, Jun 06, 2025 - Sun, Jun 08, 2025From$386Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Mon, Jan 12, 2026 - Fri, Jan 23, 2026From$249Seen: 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