Find The Best Flight Deals from $158

Travel Throughout the Caribbean with Winair, with these best one way flight deals

Philipsburg, Sint Maarten (SXM)to

Gustavia, Saint Barthélemy (SBH)
Depart: Sat, Jan 25, 2025
From
$158*
Seen: 1 day ago
One-way

Gustavia, Saint Barthélemy (SBH)to

Philipsburg, Sint Maarten (SXM)
Depart: Fri, Feb 07, 2025
From
$110*
Seen: 1 day ago
One-way

Philipsburg, Sint Maarten (SXM)to

The Bottom, Saba (SAB)
Depart: Sat, Feb 01, 2025
From
$139*
Seen: 1 day ago
One-way

Philipsburg, Sint Maarten (SXM)to

Willemstad, Curacao (CUR)
Depart: Fri, Feb 07, 2025
From
$217*
Seen: 1 day ago
One-way

Willemstad, Curacao (CUR)to

Philipsburg, Sint Maarten (SXM)
Depart: Wed, Jan 22, 2025
From
$194*
Seen: 1 day ago
One-way

St. John's, Antigua (ANU)to

Philipsburg, Sint Maarten (SXM)
Depart: Mon, Dec 30, 2024
From
$170*
Seen: 1 day ago
One-way

Oranjestad, Aruba (AUA)to

Willemstad, Curacao (CUR)
Depart: Sun, Dec 22, 2024
From
$139*
Seen: 1 day ago
One-way

Road Town, Tortola (EIS)to

Philipsburg, Sint Maarten (SXM)
Depart: Sat, Feb 01, 2025
From
$161*
Seen: 1 day ago
One-way

Philipsburg, Sint Maarten (SXM)to

Road Town, Tortola (EIS)
Depart: Fri, Jan 31, 2025
From
$205*
Seen: 1 day ago
One-way

Marigot, Dominica (DOM)to

Philipsburg, Sint Maarten (SXM)
Depart: Sun, Jan 12, 2025
From
$168*
Seen: 1 day ago
One-way

Philipsburg, Sint Maarten (SXM)to

Oranjestad, St. Eustatius (EUX)
Depart: Wed, Dec 11, 2024
From
$145*
Seen: 1 day ago
One-way

Basseterre, Saint Kitts (SKB)to

Philipsburg, Sint Maarten (SXM)
Depart: Thu, Dec 19, 2024
From
$156*
Seen: 1 day ago
One-way

*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

Popular Flight Deals with Winair
From
To
Fare Type
Dates
Price
FromPhilipsburg, Sint Maarten (SXM)ToGustavia, Saint Barthélemy (SBH)Round-tripMon, Nov 25, 2024 - Mon, Nov 25, 2024

From

$100*

Seen: 6 hrs ago

FromPhilipsburg, Sint Maarten (SXM)ToGustavia, Saint Barthélemy (SBH)Round-tripTue, Nov 26, 2024 - Tue, Nov 26, 2024

From

$100*

Seen: 3 hrs ago

FromGustavia, Saint Barthélemy (SBH)ToPhilipsburg, Sint Maarten (SXM)Round-tripSun, Dec 15, 2024 - Sat, Dec 21, 2024

From

$263*

Seen: 1 day ago

FromGustavia, Saint Barthélemy (SBH)ToPhilipsburg, Sint Maarten (SXM)Round-tripTue, May 06, 2025 - Tue, May 06, 2025

From

$263*

Seen: 1 day ago

FromPhilipsburg, Sint Maarten (SXM)ToWillemstad, Curacao (CUR)Round-tripWed, Aug 27, 2025 - Sun, Aug 31, 2025

From

$410*

Seen: 7 hrs ago

FromPhilipsburg, Sint Maarten (SXM)ToThe Bottom, Saba (SAB)Round-tripFri, Nov 29, 2024 - Fri, Nov 29, 2024

From

$79*

Seen: 11 hrs ago

FromPhilipsburg, Sint Maarten (SXM)ToThe Bottom, Saba (SAB)Round-tripMon, Nov 25, 2024 - Mon, Nov 25, 2024

From

$79*

Seen: 23 minutes ago

FromWillemstad, Curacao (CUR)ToPhilipsburg, Sint Maarten (SXM)Round-tripWed, Dec 18, 2024 - Sat, Dec 21, 2024

From

$410*

Seen: 1 day ago

FromWillemstad, Curacao (CUR)ToPhilipsburg, Sint Maarten (SXM)Round-tripThu, Sep 04, 2025 - Sun, Sep 07, 2025

From

$410*

Seen: 1 day ago

FromPhilipsburg, Sint Maarten (SXM)ToWillemstad, Curacao (CUR)Round-tripTue, Jul 29, 2025 - Sat, Aug 09, 2025

From

$410*

Seen: 1 day ago

FromOranjestad, Aruba (AUA)ToWillemstad, Curacao (CUR)Round-tripSun, Nov 24, 2024 - Thu, Nov 28, 2024

From

$261*

Seen: 6 hrs ago

FromOranjestad, Aruba (AUA)ToWillemstad, Curacao (CUR)Round-tripTue, Jan 07, 2025 - Sat, Jan 18, 2025

From

$261*

Seen: 21 hrs ago

FromPhilipsburg, Sint Maarten (SXM)ToBasseterre, Saint Kitts (SKB)Round-tripFri, Apr 25, 2025 - Tue, Apr 29, 2025

From

$355*

Seen: 1 day ago

FromRoad Town, Tortola (EIS)ToPhilipsburg, Sint Maarten (SXM)Round-tripMon, Dec 16, 2024 - Wed, Dec 18, 2024

From

$366*

Seen: 1 day ago

FromRoad Town, Tortola (EIS)ToPhilipsburg, Sint Maarten (SXM)Round-tripThu, Jan 23, 2025 - Sun, Jan 26, 2025

From

$366*

Seen: 1 day ago

FromPhilipsburg, Sint Maarten (SXM)ToRoad Town, Tortola (EIS)Round-tripThu, Nov 28, 2024 - Tue, Dec 03, 2024

From

$366*

Seen: 1 day ago

FromPhilipsburg, Sint Maarten (SXM)ToRoad Town, Tortola (EIS)Round-tripTue, Feb 11, 2025 - Sat, Feb 15, 2025

From

$366*

Seen: 23 hrs ago

FromMarigot, Dominica (DOM)ToPhilipsburg, Sint Maarten (SXM)Round-tripThu, Jul 31, 2025 - Sun, Aug 31, 2025

From

$395*

Seen: 1 day ago

FromMarigot, Dominica (DOM)ToPhilipsburg, Sint Maarten (SXM)Round-tripWed, Nov 27, 2024 - Sat, Nov 30, 2024

From

$395*

Seen: 1 day ago

FromPhilipsburg, Sint Maarten (SXM)ToBasseterre, Saint Kitts (SKB)Round-tripMon, Mar 03, 2025 - Wed, Mar 05, 2025

From

$355*

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

All route statuses
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

* The information provided is for informational purposes only and does not constitute any legal or other right. It is subject to change without notice.

Most Popular Round trip Flight Deals with Winair

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.

Popular flights from Winair