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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)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)*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, Jul 19, 2025 - Fri, Jul 25, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Jul 03, 2025 - Sun, Jul 06, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, May 22, 2025 - Thu, May 22, 2025 | From $190 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Sep 12, 2025 - Fri, Sep 19, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Oct 05, 2025 - Sat, Oct 11, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Jul 19, 2025 - Sat, Jul 26, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Fri, May 30, 2025 - Fri, May 30, 2025 | From $130 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Sat, Jul 12, 2025 - Sat, Jul 19, 2025 | From $356 Seen: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Nov 27, 2025 - Thu, Nov 27, 2025 | From $130 Seen: 17 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, Jan 14, 2026 - Sun, Jan 18, 2026 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, May 21, 2025 - Fri, Jun 06, 2025 | From $396 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 23, 2025 - Sat, Jul 05, 2025 | From $356 Seen: 1 day ago |
| Road Town, Tortola (EIS) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, May 23, 2025 - Fri, May 30, 2025 | From $367 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 27, 2025 - Sat, Aug 09, 2025 | From $396 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Fri, Jan 02, 2026 - Sat, Jan 10, 2026 | From $260 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 29, 2025 - Tue, Sep 02, 2025 | From $260 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Tue, Oct 28, 2025 - Tue, Oct 28, 2025 | From $165 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Jun 27, 2025 - Sun, Jun 29, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Aug 13, 2025 - Wed, Aug 20, 2025 | From $249 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Wed, Dec 24, 2025 - Sun, Jan 04, 2026 | 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
Willemstad, Curacao (CUR)Sat, Jul 19, 2025 - Fri, Jul 25, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Jul 03, 2025 - Sun, Jul 06, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, May 22, 2025 - Thu, May 22, 2025From$190Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Fri, Sep 12, 2025 - Fri, Sep 19, 2025From$398Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Sun, Oct 05, 2025 - Sat, Oct 11, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Jul 19, 2025 - Sat, Jul 26, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Fri, May 30, 2025 - Fri, May 30, 2025From$130Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Sat, Jul 12, 2025 - Sat, Jul 19, 2025From$356Seen: 16 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Thu, Nov 27, 2025 - Thu, Nov 27, 2025From$130Seen: 17 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Wed, Jan 14, 2026 - Sun, Jan 18, 2026From$396Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Wed, May 21, 2025 - Fri, Jun 06, 2025From$396Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Mon, Jun 23, 2025 - Sat, Jul 05, 2025From$356Seen: 1 day agoRound-tripRoad Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Fri, May 23, 2025 - Fri, May 30, 2025From$367Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Sun, Jul 27, 2025 - Sat, Aug 09, 2025From$396Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Fri, Jan 02, 2026 - Sat, Jan 10, 2026From$260Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Fri, Aug 29, 2025 - Tue, Sep 02, 2025From$260Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Tue, Oct 28, 2025 - Tue, Oct 28, 2025From$165Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Fri, Jun 27, 2025 - Sun, Jun 29, 2025From$249Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Wed, Aug 13, 2025 - Wed, Aug 20, 2025From$249Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Wed, Dec 24, 2025 - Sun, Jan 04, 2026From$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