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Caribbean Islands

$140+ Cheap flights from Simpson Bay (SXM) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — SJU
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Simpson Bay to Caribbean Islands

Cheapest flights from Simpson Bay to Caribbean Islands
Explore the most affordable flight options available from Simpson Bay to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This Trip.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1711:30 amSXM - SBH
Nonstop0h 15mFlexFlight
Wed 12/174:15 pmSBH - SXM
Nonstop0h 15mFlexFlight
Deal found 12/15$186
This SmartFares deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:00 amSXM - SBH
Nonstop0h 15mFlexFlight
Wed 12/244:00 pmSBH - SXM
Nonstop0h 15mFlexFlight
Deal found 12/14$187
This Trip.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1610:00 amSXM - SBH
Nonstop0h 15mFlexFlight
Tue 12/164:00 pmSBH - SXM
Nonstop0h 15mFlexFlight
Deal found 12/15$189
This CheapOair deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:30 amSXM - SBH
Nonstop0h 15mFlexFlight
Wed 12/174:00 pmSBH - SXM
Nonstop0h 15mFlexFlight
Deal found 12/14$207
This CheapOair deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:30 amSXM - SBH
Nonstop0h 15mMultiple Airlines
Thu 1/85:50 pmSBH - SXM
Nonstop0h 15mMultiple Airlines
Deal found 12/15$257
This Travelocity deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:05 amSXM - SBH
Nonstop0h 15mMultiple Airlines
Thu 1/14:15 pmSBH - SXM
Nonstop0h 15mMultiple Airlines
Deal found 12/15$277
This SmartFares deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2611:00 amSXM - SBH
Nonstop0h 15mWinair
Fri 12/265:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 12/14$286
This CheapOair deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3010:00 amSXM - SBH
Nonstop0h 15mMultiple Airlines
Sun 1/44:30 pmSBH - SXM
Nonstop0h 15mMultiple Airlines
Deal found 12/14$292
This Expedia deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1911:30 amSXM - SBH
Nonstop0h 15mMultiple Airlines
Sun 12/211:40 pmSBH - SXM
Nonstop0h 15mMultiple Airlines
Deal found 12/15$304
This Winair deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Winair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:30 amSXM - SBH
Nonstop0h 15mWinair
Mon 12/295:35 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 12/15$310
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:30 amSXM - SDQ
Nonstop1h 30mArajet
Wed 12/317:03 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 12/15$314
This FlightHub deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amSXM - SBH
Nonstop0h 15mWinair
Fri 1/25:20 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 12/15$320

Find flight deals from Simpson Bay to Caribbean Islands

Keep the following information in mind while searching for Simpson Bay to Caribbean Islands flight deals. Data was last updated December 16, 2025.

Round-trip from

$186
(Trip.com)

One-way from

$140
(Kiwi.com)

Popular in

November

Cheapest in

March

Average price

$315
From Simpson Bay Princess Juliana to Caribbean Islands
Search Deals
One-way flight from Simpson Bay Princess Juliana to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 34% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 16, 2025.
Use the filters below to find and compare flights from Simpson Bay to Caribbean Islands that are best for you.

Fly from

Simpson Bay

Fly to

Caribbean Islands

Route

Depart

Return

Price

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Sat 1/10

10:00 am-10:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Wed 1/14

4:00 pm-4:15 pm

Nonstop0h 15m

$186

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 1/14

11:30 am-11:45 am

Nonstop0h 15m

Gustavia St Barthelemy

Wed 1/14

4:15 pm-4:30 pm

Nonstop0h 15m

$186

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 4/10

11:30 am-11:45 am

Nonstop0h 15m

Gustavia St Barthelemy

Tue 4/14

4:00 pm-4:15 pm

Nonstop0h 15m

$187

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 2/18

11:30 am-11:45 am

Nonstop0h 15m

Gustavia St Barthelemy

Thu 2/19

4:15 pm-4:30 pm

Nonstop0h 15m

$206

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 1/16

11:30 am-11:45 am

Nonstop0h 15m

Gustavia St Barthelemy

Tue 1/20

4:00 pm-4:15 pm

Nonstop0h 15m

$207

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Sat 1/17

10:00 am-10:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Sun 1/25

5:25 pm-5:40 pm

Nonstop0h 15m

$239

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Tue 1/13

1:45 pm-2:50 pm

Nonstop1h 05m

San Juan Luis Munoz Marin Intl

Tue 1/20

6:14 pm-11:24 am

1 stop17h 10m

$273

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Tue 1/13

1:45 pm-2:50 pm

Nonstop1h 05m

San Juan Luis Munoz Marin Intl

Tue 1/20

11:40 am-12:45 pm

Nonstop1h 05m

$298

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Fri 1/30

1:45 pm-2:50 pm

Nonstop1h 05m

San Juan Luis Munoz Marin Intl

Fri 2/6

11:40 am-12:45 pm

Nonstop1h 05m

$298

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Tue 2/17

1:45 pm-2:50 pm

Nonstop1h 05m

San Juan Luis Munoz Marin Intl

Tue 3/3

11:40 am-12:45 pm

Nonstop1h 05m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 60 results
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Best time to book a flight from Simpson Bay to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Simpson Bay with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Simpson Bay to Caribbean Islands

What is the cheapest month to book a flight from Simpson Bay to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Simpson Bay to Caribbean Islands (average of $73). Flying from Simpson Bay to Caribbean Islands in September is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SXM to EPX?

Find hourly flight availability from Simpson Bay to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 16, 2025.

It’s typically best to fly out from Simpson Bay to Caribbean Islands in the morning. Doing so could potentially save you 13% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated December 16, 2025.
Read reviews from past customers who have flown Caribbean Airlines from Simpson Bay to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.0
Very good
209 reviews

Boarding

8.0

Overall

8.0

Comfort

7.8

Food

6.8

Crew

8.4

Entertainment

6.6

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
Caribbean Airlines
8.0
Very good
209 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Boarding

8.0

Overall

8.0

Comfort

7.8

Food

6.8

Crew

8.4

Entertainment

6.6

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Simpson Bay to Caribbean Islands?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana (SXM) is the airport most travelers will use when flying to Caribbean Islands from Simpson Bay.

  • How long is the flight from Simpson Bay to Caribbean Islands?

    Airlines like FlexFlight, Contour, and Winair fly from Simpson Bay to Caribbean Islands in about 15m. The time it takes to get you to your destination is usually consistent. The distance from Simpson Bay to Caribbean Islands is about 20 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Simpson Bay to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as $103 on Frontier. Other airlines that offer cheap prices include FlexFlight from $122 and Winair from $127 one-way.

  • What are the most popular routes from Simpson Bay to Caribbean Islands?

    When deciding which route to take from Simpson Bay to Caribbean Islands consider Simpson Bay Princess Juliana - Gustavia St Barthelemy, Simpson Bay Princess Juliana - San Juan Luis Munoz Marin Intl or Simpson Bay Princess Juliana - Kingston Norman Manley as they are the most popular.

  • What are the cheapest flights from Simpson Bay to Caribbean Islands?

    Looking at all options, your cheapest flight can be booked for $168. While the most popular route (Simpson Bay Princess Juliana - Gustavia St Barthelemy) can be booked for $248 on average, our data indicates $295 when flying from Simpson Bay to Caribbean Islands.

  • Can I find deals for flights from Simpson Bay to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Simpson Bay to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Simpson Bay to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Simpson Bay to Caribbean Islands.

  • Can I find deals for business class flights from Simpson Bay to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Simpson Bay to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Simpson Bay to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Simpson Bay to Caribbean Islands (average of $73). Flying from Simpson Bay to Caribbean Islands in September is currently the most expensive (average of $231). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 5 airlines flying from Simpson Bay to Caribbean Islands

Discover the top 5 airlines that operate flights from Simpson Bay to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$184FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$187Average$336FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$198Average$290FlexibilityNo cancel feeOn-timeN/A
ContourCheapest$240Average$350FlexibilityNo cancel feeOn-timeN/A
WinairCheapest$359Average$482FlexibilityNo cancel feeOn-timeN/A

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