Find The Best Flight Deals from $73
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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Road Town, Tortola (EIS)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 | Sat, Oct 04, 2025 - Sat, Oct 11, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Jul 23, 2025 - Wed, Jul 23, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sun, Mar 15, 2026 - Sun, Mar 22, 2026 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Thu, Oct 23, 2025 - Mon, Oct 27, 2025 | From $365 Seen: 15 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Jul 22, 2025 - Tue, Jul 22, 2025 | From $263 Seen: 15 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Sun, Jul 27, 2025 | From $263 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Thu, Aug 21, 2025 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Fri, Aug 22, 2025 | From $283 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sat, Jul 26, 2025 - Sat, Jul 26, 2025 | From $167 Seen: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Wed, Jul 30, 2025 - Thu, Jul 31, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Oct 06, 2025 - Tue, Oct 14, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Mon, Jul 28, 2025 - Mon, Jul 28, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Wed, Jul 23, 2025 - Wed, Jul 23, 2025 | From $167 Seen: 20 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jan 02, 2026 - Sun, Jan 11, 2026 | From $396 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sat, Nov 08, 2025 - Sun, Nov 16, 2025 | From $250 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Sep 13, 2025 - Sun, Sep 21, 2025 | From $365 Seen: 10 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Oct 18, 2025 - Sat, Oct 25, 2025 | From $365 Seen: 4 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 21, 2025 - Thu, Aug 28, 2025 | From $396 Seen: 15 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | Fri, Feb 13, 2026 - Sun, Feb 15, 2026 | From $367 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Road Town, Tortola (EIS) | Round-trip | Thu, Mar 12, 2026 - Thu, Mar 26, 2026 | 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 04, 2025 - Sat, Oct 11, 2025From$365Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Jul 23, 2025 - Wed, Jul 23, 2025From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sun, Mar 15, 2026 - Sun, Mar 22, 2026From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Thu, Oct 23, 2025 - Mon, Oct 27, 2025From$365Seen: 15 hrs 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 - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - The Bottom, Saba
- Philipsburg, Sint Maarten - Marigot, Dominica
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Road Town, Tortola - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - St. John's, Antigua