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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)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Oranjestad, St. Eustatius (EUX)to
Philipsburg, Sint Maarten (SXM)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)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) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Jun 30, 2025 - Mon, Jun 30, 2025 | From $263 Seen: 6 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Mon, Jun 23, 2025 - Mon, Jun 23, 2025 | From $263 Seen: 6 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Sat, Dec 13, 2025 - Mon, Feb 02, 2026 | From $397 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Oct 06, 2025 - Wed, Oct 08, 2025 | From $397 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Dec 03, 2025 - Sun, Dec 07, 2025 | From $263 Seen: 42 minutes ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Oct 03, 2025 - Wed, Oct 08, 2025 | From $263 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Fri, Jan 16, 2026 - Wed, Jan 21, 2026 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Aug 04, 2025 - Mon, Aug 11, 2025 | From $396 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Dec 19, 2025 - Mon, Jan 05, 2026 | From $397 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 11, 2025 - Sun, Sep 14, 2025 | From $397 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Jul 17, 2025 - Thu, Jul 24, 2025 | From $337 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Basseterre, Saint Kitts (SKB) | Round-trip | Mon, Nov 24, 2025 - Thu, Nov 27, 2025 | From $337 Seen: 20 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Jul 13, 2025 - Sun, Jul 13, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Jun 19, 2025 - Thu, Jun 19, 2025 | From $199 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Oct 17, 2025 - Fri, Oct 24, 2025 | From $238 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Jul 20, 2025 - Thu, Jul 24, 2025 | From $386 Seen: 1 day ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Aug 11, 2025 - Sun, Aug 17, 2025 | From $386 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Fri, Feb 27, 2026 - Sat, Mar 07, 2026 | From $236 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Fri, Nov 07, 2025 - Sat, Nov 15, 2025 | From $238 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 18, 2025 - Mon, Sep 22, 2025 | From $337 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
Gustavia, Saint Barthélemy (SBH)Mon, Jun 30, 2025 - Mon, Jun 30, 2025From$263Seen: 6 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Mon, Jun 23, 2025 - Mon, Jun 23, 2025From$263Seen: 6 hrs agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Sat, Dec 13, 2025 - Mon, Feb 02, 2026From$397Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Oct 06, 2025 - Wed, Oct 08, 2025From$397Seen: 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
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - Willemstad, Curacao
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Philipsburg, Sint Maarten - St. John's, Antigua
- Philipsburg, Sint Maarten - The Bottom, Saba
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Oranjestad, Aruba
- St. John's, Antigua - Philipsburg, Sint Maarten
- The Bottom, Saba - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius