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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)Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Charlestown, Nevis (NEV)to
Philipsburg, Sint Maarten (SXM)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)*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) | Willemstad, Curacao (CUR) | Round-trip | Sat, Oct 18, 2025 - Sat, Oct 25, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Tue, Jul 01, 2025 - Thu, Jul 10, 2025 | From $398 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Apr 19, 2025 - Tue, Apr 29, 2025 | From $356 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Apr 27, 2025 - Wed, Apr 30, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Tue, Dec 16, 2025 - Sun, Dec 21, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Apr 28, 2025 - Wed, Apr 30, 2025 | From $190 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jul 09, 2025 - Thu, Jul 10, 2025 | From $398 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jul 25, 2025 - Wed, Aug 20, 2025 | From $356 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Aug 06, 2025 - Sun, Aug 17, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Sep 09, 2025 - Thu, Sep 25, 2025 | From $249 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Mon, May 19, 2025 - Fri, May 23, 2025 | From $260 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sun, Aug 24, 2025 - Mon, Aug 25, 2025 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sat, May 03, 2025 - Sat, May 10, 2025 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, May 14, 2025 - Mon, Jun 09, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Jul 04, 2025 - Thu, Jul 17, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 28, 2025 - Fri, Aug 08, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Apr 10, 2025 - Fri, May 02, 2025 | From $396 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Apr 08, 2025 - Sat, May 10, 2025 | From $386 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Sep 17, 2025 - Wed, Sep 24, 2025 | From $386 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Apr 03, 2025 - Tue, Apr 15, 2025 | From $367 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
Willemstad, Curacao (CUR)Sat, Oct 18, 2025 - Sat, Oct 25, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Tue, Jul 01, 2025 - Thu, Jul 10, 2025From$398Seen: 1 day agoRound-trip
Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sat, Apr 19, 2025 - Tue, Apr 29, 2025From$356Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Sun, Apr 27, 2025 - Wed, Apr 30, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Tue, Dec 16, 2025 - Sun, Dec 21, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Mon, Apr 28, 2025 - Wed, Apr 30, 2025From$190Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Wed, Jul 09, 2025 - Thu, Jul 10, 2025From$398Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Fri, Jul 25, 2025 - Wed, Aug 20, 2025From$356Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Wed, Aug 06, 2025 - Sun, Aug 17, 2025From$249Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Tue, Sep 09, 2025 - Thu, Sep 25, 2025From$249Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Mon, May 19, 2025 - Fri, May 23, 2025From$260Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Sun, Aug 24, 2025 - Mon, Aug 25, 2025From$356Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Sat, May 03, 2025 - Sat, May 10, 2025From$356Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Wed, May 14, 2025 - Mon, Jun 09, 2025From$396Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Fri, Jul 04, 2025 - Thu, Jul 17, 2025From$396Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Mon, Jul 28, 2025 - Fri, Aug 08, 2025From$396Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Thu, Apr 10, 2025 - Fri, May 02, 2025From$396Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Tue, Apr 08, 2025 - Sat, May 10, 2025From$386Seen: 1 day agoRound-tripSt. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Wed, Sep 17, 2025 - Wed, Sep 24, 2025From$386Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Thu, Apr 03, 2025 - Tue, Apr 15, 2025From$367Seen: 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 - Fort-de-France, Martinique
- Bridgetown, Barbados - Charlestown, Nevis
- Bridgetown, Barbados - Basseterre, Saint Kitts
- Bridgetown, Barbados - Marigot, Dominica
- Bridgetown, Barbados - St. John's, Antigua
- Bridgetown, Barbados - Castries, Saint Lucia
- Bridgetown, Barbados - Oranjestad, Aruba
- Bridgetown, Barbados - Road Town, Tortola
- Bridgetown, Barbados - Kingstown, Saint Vincent
- Bridgetown, Barbados - Gustavia, Saint Barthélemy
- Bridgetown, Barbados - The Bottom, Saba