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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
Oranjestad, Aruba (AUA)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)*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, Jul 11, 2025 - Sat, Jul 19, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Dec 20, 2025 - Sat, Dec 27, 2025 | From $398 Seen: 12 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Dec 22, 2025 - Mon, Jan 05, 2026 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Mar 25, 2026 - Sun, Mar 29, 2026 | From $190 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Sun, Mar 01, 2026 - Fri, Mar 06, 2026 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Oct 30, 2025 - Tue, Dec 16, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Mar 01, 2026 - Wed, Mar 11, 2026 | From $398 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, May 15, 2025 - Mon, May 19, 2025 | From $269 Seen: 7 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, May 11, 2025 - Sun, May 11, 2025 | From $269 Seen: 6 hrs ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, May 23, 2025 - Sat, May 31, 2025 | From $249 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jul 13, 2025 - Sun, Jul 13, 2025 | From $130 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Dec 22, 2025 - Mon, Dec 22, 2025 | From $130 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Sep 30, 2025 - Wed, Oct 08, 2025 | From $356 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jun 01, 2025 - Sun, Jun 08, 2025 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | Mon, May 12, 2025 - Sat, May 17, 2025 | From $386 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | Mon, May 26, 2025 - Mon, May 26, 2025 | From $386 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Sat, Jul 19, 2025 - Sun, Jul 27, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Tue, Oct 21, 2025 - Wed, Oct 29, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sat, Feb 07, 2026 - Sat, Feb 14, 2026 | From $238 Seen: 9 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Nov 26, 2025 - Sun, Nov 30, 2025 | From $617 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, Jul 11, 2025 - Sat, Jul 19, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Dec 20, 2025 - Sat, Dec 27, 2025From$398Seen: 12 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Mon, Dec 22, 2025 - Mon, Jan 05, 2026From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Mar 25, 2026 - Sun, Mar 29, 2026From$190Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Sun, Mar 01, 2026 - Fri, Mar 06, 2026From$249Seen: 1 day agoRound-trip
Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Thu, Oct 30, 2025 - Tue, Dec 16, 2025From$398Seen: 1 day agoRound-tripWillemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Sun, Mar 01, 2026 - Wed, Mar 11, 2026From$398Seen: 1 day agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Thu, May 15, 2025 - Mon, May 19, 2025From$269Seen: 7 hrs agoRound-tripGustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Sun, May 11, 2025 - Sun, May 11, 2025From$269Seen: 6 hrs agoRound-tripWillemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Fri, May 23, 2025 - Sat, May 31, 2025From$249Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Sun, Jul 13, 2025 - Sun, Jul 13, 2025From$130Seen: 23 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Mon, Dec 22, 2025 - Mon, Dec 22, 2025From$130Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Tue, Sep 30, 2025 - Wed, Oct 08, 2025From$356Seen: 1 day agoRound-tripBasseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Sun, Jun 01, 2025 - Sun, Jun 08, 2025From$356Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Mon, May 12, 2025 - Sat, May 17, 2025From$386Seen: 20 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)Mon, May 26, 2025 - Mon, May 26, 2025From$386Seen: 21 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Sat, Jul 19, 2025 - Sun, Jul 27, 2025From$396Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Tue, Oct 21, 2025 - Wed, Oct 29, 2025From$396Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Sat, Feb 07, 2026 - Sat, Feb 14, 2026From$238Seen: 9 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Oranjestad, Aruba (AUA)Wed, Nov 26, 2025 - Sun, Nov 30, 2025From$617Seen: 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