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)Marigot, Dominica (DOM)to
Philipsburg, Sint Maarten (SXM)Oranjestad, Aruba (AUA)to
Willemstad, Curacao (CUR)Philipsburg, Sint Maarten (SXM)to
Marigot, Dominica (DOM)Philipsburg, Sint Maarten (SXM)to
Oranjestad, St. Eustatius (EUX)Basseterre, Saint Kitts (SKB)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Oranjestad, Aruba (AUA)Road Town, Tortola (EIS)to
Philipsburg, Sint Maarten (SXM)Gustavia, Saint Barthélemy (SBH)to
Philipsburg, Sint Maarten (SXM)Willemstad, Curacao (CUR)to
Philipsburg, Sint Maarten (SXM)Philipsburg, Sint Maarten (SXM)to
The Bottom, Saba (SAB)*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, Sep 02, 2025 - Tue, Sep 09, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Willemstad, Curacao (CUR) | Round-trip | Mon, Sep 08, 2025 - Sun, Sep 14, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Wed, Mar 04, 2026 - Wed, Mar 04, 2026 | From $185 Seen: 14 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Gustavia, Saint Barthélemy (SBH) | Round-trip | Thu, Feb 12, 2026 - Wed, Feb 18, 2026 | From $185 Seen: 14 hrs ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Aug 10, 2025 - Wed, Aug 20, 2025 | From $396 Seen: 1 day ago |
| Marigot, Dominica (DOM) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Aug 21, 2025 - Mon, Aug 25, 2025 | From $396 Seen: 1 day ago |
| Oranjestad, Aruba (AUA) | Willemstad, Curacao (CUR) | Round-trip | Sat, Jan 31, 2026 - Tue, Feb 10, 2026 | From $250 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Tue, Oct 07, 2025 - Sun, Oct 12, 2025 | From $396 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Marigot, Dominica (DOM) | Round-trip | Tue, Oct 28, 2025 - Mon, Jan 12, 2026 | From $396 Seen: 1 day ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Sun, Jul 27, 2025 | From $263 Seen: 15 hrs ago |
| Gustavia, Saint Barthélemy (SBH) | Philipsburg, Sint Maarten (SXM) | Round-trip | Mon, Jul 21, 2025 - Mon, Jul 21, 2025 | From $263 Seen: 8 hrs ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Mon, Jul 21, 2025 - Mon, Jul 21, 2025 | From $167 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | Oranjestad, St. Eustatius (EUX) | Round-trip | Sun, Aug 10, 2025 - Sun, Aug 10, 2025 | From $199 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Jul 26, 2025 - Mon, Aug 18, 2025 | From $283 Seen: 1 day ago |
| Basseterre, Saint Kitts (SKB) | Philipsburg, Sint Maarten (SXM) | Round-trip | Thu, Sep 18, 2025 - Mon, Sep 22, 2025 | From $283 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Oranjestad, Aruba (AUA) | Round-trip | Thu, Oct 02, 2025 - Sun, Oct 05, 2025 | From $238 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sun, Oct 19, 2025 - Sun, Oct 26, 2025 | From $365 Seen: 1 day ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Thu, Jul 24, 2025 - Thu, Jul 24, 2025 | From $167 Seen: 11 hrs ago |
| Philipsburg, Sint Maarten (SXM) | The Bottom, Saba (SAB) | Round-trip | Wed, Jul 23, 2025 - Wed, Jul 23, 2025 | From $167 Seen: 1 day ago |
| Willemstad, Curacao (CUR) | Philipsburg, Sint Maarten (SXM) | Round-trip | Sat, Sep 13, 2025 - Sun, Sep 21, 2025 | From $365 Seen: 8 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)Tue, Sep 02, 2025 - Tue, Sep 09, 2025From$365Seen: 1 day agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Willemstad, Curacao (CUR)Mon, Sep 08, 2025 - Sun, Sep 14, 2025From$365Seen: 1 day agoRound-trip
Philipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Wed, Mar 04, 2026 - Wed, Mar 04, 2026From$185Seen: 14 hrs agoRound-tripPhilipsburg, Sint Maarten (SXM)to
Gustavia, Saint Barthélemy (SBH)Thu, Feb 12, 2026 - Wed, Feb 18, 2026From$185Seen: 14 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
- Gustavia, Saint Barthélemy - Philipsburg, Sint Maarten
- Basseterre, Saint Kitts - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Marigot, Dominica
- Philipsburg, Sint Maarten - Oranjestad, St. Eustatius
- Philipsburg, Sint Maarten - The Bottom, Saba
- Willemstad, Curacao - Philipsburg, Sint Maarten
- Marigot, Dominica - Philipsburg, Sint Maarten
- Oranjestad, Aruba - Willemstad, Curacao
- Willemstad, Curacao - Oranjestad, Aruba
- Philipsburg, Sint Maarten - Road Town, Tortola
- Oranjestad, St. Eustatius - Philipsburg, Sint Maarten
- Philipsburg, Sint Maarten - Basseterre, Saint Kitts
- Road Town, Tortola - Philipsburg, Sint Maarten