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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)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)St. John's, Antigua (ANU)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
Basseterre, Saint Kitts (SKB)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
St. John's, Antigua (ANU)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 | Wed, Nov 26, 2025 - Sat, Nov 29, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Wed, Jul 30, 2025 - Wed, Jul 30, 2025 | From $398 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Tue, Jul 22, 2025 - Tue, Jul 29, 2025 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Jan 29, 2026 - Sun, Feb 01, 2026 | From $190 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Sun, Oct 05, 2025 - Sun, Oct 05, 2025 | From $130 Seen: 18 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Tue, Jun 17, 2025 - Tue, Jun 17, 2025 | From $130 Seen: 11 hrs ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 04, 2025 - Mon, Sep 08, 2025 | From $398 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Wed, Jan 28, 2026 - Wed, Jan 28, 2026 | From $249 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Mon, Oct 06, 2025 - Fri, Oct 10, 2025 | From $249 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jun 23, 2025 - Sat, Jul 19, 2025 | From $356 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jun 11, 2025 - Sat, Jun 14, 2025 | From $356 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Dec 08, 2025 - Mon, Dec 15, 2025 | From $396 Seen: 19 hrs ago |
| St. John's, Antigua (ANU) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Aug 08, 2025 - Mon, Aug 11, 2025 | From $386 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Fri, Jul 11, 2025 - Wed, Jul 16, 2025 | From $398 Seen: 21 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Mon, Aug 18, 2025 - Mon, Aug 25, 2025 | From $396 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Wed, Jun 11, 2025 - Wed, Jun 11, 2025 | From $269 Seen: 22 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Tue, Jun 10, 2025 - Tue, Jun 10, 2025 | From $269 Seen: 22 hrs ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | Fri, Jun 27, 2025 - Mon, Jun 30, 2025 | From $386 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | St. John's, Antigua (ANU) | Round-trip | Tue, Mar 03, 2026 - Tue, Mar 03, 2026 | From $386 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sat, Jun 14, 2025 - Sat, Jun 14, 2025 | From $133 Seen: 21 hrs 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)Wed, Nov 26, 2025 - Sat, Nov 29, 2025From$398Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Wed, Jul 30, 2025 - Wed, Jul 30, 2025From$398Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Tue, Jul 22, 2025 - Tue, Jul 29, 2025From$190Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Jan 29, 2026 - Sun, Feb 01, 2026From$190Seen: 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 - Willemstad, Curacao
- Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Marigot, Dominica
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Philipsburg, Sint Maarten - St. John's, Antigua
- Oranjestad, Aruba - Willemstad, Curacao
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Marigot, Dominica - Philipsburg, Sint Maarten
- Road Town, Tortola - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Castries, Saint Lucia