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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)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) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 01, 2025 - Thu, Aug 07, 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: 16 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Tue, Jun 03, 2025 - Thu, Jun 12, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, May 22, 2025 - Mon, May 26, 2025 | From $190 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jun 29, 2025 - Tue, Jul 22, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Jul 24, 2025 - Sun, Jul 27, 2025 | From $398 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, May 27, 2025 - Tue, May 27, 2025 | From $269 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jul 30, 2025 - Fri, Aug 08, 2025 | From $269 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: 3 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, May 20, 2025 - Tue, May 20, 2025 | From $130 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sat, Dec 20, 2025 - Sun, Jan 04, 2026 | From $260 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Thu, Jul 24, 2025 - Thu, Jul 31, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Thu, Aug 07, 2025 - Thu, Oct 09, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, May 23, 2025 - Mon, May 26, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 27, 2025 - Sat, Aug 09, 2025 | From $396 Seen: 10 hrs ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Fri, Aug 29, 2025 - Tue, Sep 02, 2025 | From $260 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, May 18, 2025 - Sun, May 18, 2025 | From $133 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: 14 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Oct 01, 2025 - Sat, Oct 04, 2025 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Tue, Jun 17, 2025 - Tue, Jun 24, 2025 | 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
Willemstad, Curacao (CUR)Fri, Aug 01, 2025 - Thu, Aug 07, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Jul 19, 2025 - Sat, Jul 26, 2025From$398Seen: 16 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Tue, Jun 03, 2025 - Thu, Jun 12, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, May 22, 2025 - Mon, May 26, 2025From$190Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Sun, Jun 29, 2025 - Tue, Jul 22, 2025From$398Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Thu, Jul 24, 2025 - Sun, Jul 27, 2025From$398Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Tue, May 27, 2025 - Tue, May 27, 2025From$269Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Wed, Jul 30, 2025 - Fri, Aug 08, 2025From$269Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Fri, May 30, 2025 - Fri, May 30, 2025From$130Seen: 3 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Tue, May 20, 2025 - Tue, May 20, 2025From$130Seen: 1 day agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Sat, Dec 20, 2025 - Sun, Jan 04, 2026From$260Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Thu, Jul 24, 2025 - Thu, Jul 31, 2025From$396Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Thu, Aug 07, 2025 - Thu, Oct 09, 2025From$396Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Fri, May 23, 2025 - Mon, May 26, 2025From$396Seen: 1 day agoRound-tripMarigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Sun, Jul 27, 2025 - Sat, Aug 09, 2025From$396Seen: 10 hrs agoRound-tripOranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Fri, Aug 29, 2025 - Tue, Sep 02, 2025From$260Seen: 8 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sun, May 18, 2025 - Sun, May 18, 2025From$133Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Tue, Oct 28, 2025 - Tue, Oct 28, 2025From$165Seen: 14 hrs agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Wed, Oct 01, 2025 - Sat, Oct 04, 2025From$249Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Tue, Jun 17, 2025 - Tue, Jun 24, 2025From$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