Find The Best Flight Deals from $73
Discover our Destinations and Book your Ticket
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)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Gustavia, Saint Barthélemy (SBH)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 | Tue, Nov 18, 2025 - Sun, Nov 23, 2025 | From $365 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Thu, Oct 16, 2025 - Mon, Oct 20, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sat, Aug 16, 2025 - Sat, Aug 16, 2025 | From $185 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Sun, Jul 20, 2025 - Sat, Jul 26, 2025 | From $185 Seen: 23 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Sep 02, 2025 - Tue, Sep 02, 2025 | From $197 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jul 20, 2025 - Sun, Jul 20, 2025 | From $167 Seen: 6 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Oct 09, 2025 - Sun, Oct 12, 2025 | From $365 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 03, 2025 - Fri, Oct 10, 2025 | From $365 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Sep 10, 2025 - Sun, Sep 14, 2025 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Sun, Aug 10, 2025 - Sun, Sep 07, 2025 | From $238 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Oct 20, 2025 - Thu, Oct 30, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Feb 23, 2026 - Sun, Mar 08, 2026 | From $396 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sun, Feb 22, 2026 - Wed, Feb 25, 2026 | From $250 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Tue, Dec 30, 2025 - Sun, Jan 04, 2026 | From $250 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 21, 2025 - Sat, Aug 02, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 21, 2025 - Wed, Aug 20, 2025 | From $396 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Sep 02, 2025 - Wed, Oct 29, 2025 | From $386 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 27, 2025 - Sun, Jul 27, 2025 | From $386 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: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Jul 28, 2025 - Mon, Jul 28, 2025 | From $167 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)Tue, Nov 18, 2025 - Sun, Nov 23, 2025From$365Seen: 18 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Thu, Oct 16, 2025 - Mon, Oct 20, 2025From$365Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sat, Aug 16, 2025 - Sat, Aug 16, 2025From$185Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Sun, Jul 20, 2025 - Sat, Jul 26, 2025From$185Seen: 23 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Oranjestad, Aruba
- Oranjestad, Aruba - Willemstad, Curacao
- Philipsburg, Sint Maarten - Marigot, Dominica
- Marigot, Dominica - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Road Town, Tortola - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Road Town, Tortola
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts