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Travel Throughout the Caribbean with Winair, with these best one way flight deals
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Basseterre, Saint Kitts (SKB)to
Road Town, Tortola (EIS)Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)*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 23, 2025 - Fri, Nov 28, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jul 16, 2025 - Sat, Jul 19, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sun, May 25, 2025 - Sun, Jun 01, 2025 | From $210 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Fri, Jul 04, 2025 - Fri, Jul 04, 2025 | From $210 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jun 27, 2025 - Sun, Jun 29, 2025 | From $210 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Jun 10, 2025 - Tue, Jun 17, 2025 | From $210 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Thu, Oct 09, 2025 - Sun, Oct 12, 2025 | From $117 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Thu, Aug 28, 2025 - Tue, Sep 02, 2025 | From $117 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Thu, May 01, 2025 - Thu, May 01, 2025 | From $169 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Jun 03, 2025 - Fri, Jun 06, 2025 | From $220 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Sep 30, 2025 - Fri, Oct 03, 2025 | From $220 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, May 15, 2025 - Fri, May 30, 2025 | From $169 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, May 15, 2025 - Thu, May 15, 2025 | From $169 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Oct 15, 2025 - Sat, Oct 18, 2025 | From $117 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Jun 12, 2025 - Tue, Jun 17, 2025 | From $117 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jun 13, 2025 - Mon, Jun 16, 2025 | From $219 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 10, 2025 - Fri, Sep 12, 2025 | From $219 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Thu, May 22, 2025 - Sun, May 25, 2025 | From $169 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Thu, Jul 10, 2025 - Fri, Jul 25, 2025 | From $219 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Oct 17, 2025 - Wed, Oct 22, 2025 | From $219 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 23, 2025 - Fri, Nov 28, 2025From$190*Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jul 16, 2025 - Sat, Jul 19, 2025From$190*Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sun, May 25, 2025 - Sun, Jun 01, 2025From$210*Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Fri, Jul 04, 2025 - Fri, Jul 04, 2025From$210*Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Fri, Jun 27, 2025 - Sun, Jun 29, 2025From$210*Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Tue, Jun 10, 2025 - Tue, Jun 17, 2025From$210*Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Thu, Oct 09, 2025 - Sun, Oct 12, 2025From$117*Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Thu, Aug 28, 2025 - Tue, Sep 02, 2025From$117*Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Thu, May 01, 2025 - Thu, May 01, 2025From$169*Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Tue, Jun 03, 2025 - Fri, Jun 06, 2025From$220*Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Tue, Sep 30, 2025 - Fri, Oct 03, 2025From$220*Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Thu, May 15, 2025 - Fri, May 30, 2025From$169*Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Thu, May 15, 2025 - Thu, May 15, 2025From$169*Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Wed, Oct 15, 2025 - Sat, Oct 18, 2025From$117*Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Thu, Jun 12, 2025 - Tue, Jun 17, 2025From$117*Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Fri, Jun 13, 2025 - Mon, Jun 16, 2025From$219*Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Wed, Sep 10, 2025 - Fri, Sep 12, 2025From$219*Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Thu, May 22, 2025 - Sun, May 25, 2025From$169*Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Thu, Jul 10, 2025 - Fri, Jul 25, 2025From$219*Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Fri, Oct 17, 2025 - Wed, Oct 22, 2025From$219*Seen: 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 - Willemstad, Curacao
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Marigot, Dominica
- St. John's, Antigua - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - St. John's, Antigua
- Oranjestad, Aruba - Willemstad, Curacao
- Marigot, Dominica - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Road Town, Tortola
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Charlestown, Nevis - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Marigot, Dominica
- Road Town, Tortola - Philipsburg, Sint Maarten