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Caribbean Islands

$149+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — SJU
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
1 adult, Economy
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Cheap 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 October 10, 2025.

Round-trip from

$220
(Mytrip)

One-way from

$149
(Orbitz)

Popular in

November

Cheapest in

June

Average price

$256
From Simpson Bay Princess Juliana to Caribbean Islands
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One-way flight from Simpson Bay Princess Juliana to Caribbean Islands
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Highest demand for flights based on searches. 30% potential increase in price ($103 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 10, 2025.

This Orbitz deal was found by Cheapflights users on 10/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:35 pmSXM - SDQ
Nonstop1h 30mArajet
Thu 10/308:58 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$269
This Expedia deal was found by Cheapflights users on 10/9. 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.
Wed 10/298:57 pmSXM - SDQ
Nonstop1h 30mArajet
Wed 11/56:25 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$274
This Orbitz deal was found by Cheapflights users on 10/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:57 pmSXM - SDQ
Nonstop1h 30mArajet
Wed 11/196:25 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$276
This Travelocity deal was found by Cheapflights users on 10/8. 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.
Thu 10/165:35 pmSXM - SDQ
Nonstop1h 30mArajet
Thu 10/233:03 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/8$278
This Expedia deal was found by Cheapflights users on 10/9. 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.
Wed 11/58:57 pmSXM - SDQ
Nonstop1h 30mArajet
Wed 11/126:25 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$280
This Travelocity deal was found by Cheapflights users on 10/9. 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.
Thu 11/611:30 amSXM - SDQ
Nonstop1h 30mArajet
Thu 11/138:58 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$285
This Expedia deal was found by Cheapflights users on 10/8. 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.
Sun 10/128:35 pmSXM - SDQ
Nonstop1h 30mArajet
Wed 10/156:45 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/8$287
This SmartFares deal was found by Cheapflights users on 10/9. 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 11/129:00 amSXM - SBH
Nonstop0h 15mWinair
Wed 11/194:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 10/9$288
This Expedia deal was found by Cheapflights users on 10/9. 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.
Wed 10/159:17 amSXM - SDQ
Nonstop1h 30mArajet
Wed 10/226:45 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/9$289
This Orbitz deal was found by Cheapflights users on 10/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/119:35 amSXM - SBH
Nonstop0h 15mWinair
Sun 11/164:20 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 10/7$293
This Expedia deal was found by Cheapflights users on 10/8. 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.
Wed 12/249:35 amSXM - SDQ
Nonstop1h 30mArajet
Wed 12/317:03 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 10/8$297
This SmartFares deal was found by Cheapflights users on 10/9. 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.
Tue 12/2311:15 amSXM - SBH
Nonstop0h 15mWinair
Fri 1/25:30 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 10/9$298

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 October 10, 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 BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Sun 3/8

11:30 am-1:00 pm

Nonstop1h 30m

Santo Domingo Las Americas

Sun 3/15

8:58 am-10:25 am

Nonstop1h 27m

$223

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Sun 2/22

11:30 am-1:00 pm

Nonstop1h 30m

Santo Domingo Las Americas

Sun 3/1

8:58 am-10:25 am

Nonstop1h 27m

$223

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Sun 2/22

11:30 am-1:00 pm

Nonstop1h 30m

Santo Domingo Las Americas

Sun 3/1

8:58 am-10:25 am

Nonstop1h 27m

$251

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Wed 3/4

9:35 am-11:05 am

Nonstop1h 30m

Santo Domingo Las Americas

Wed 3/11

7:03 am-8:30 am

Nonstop1h 27m

$253

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Thu 3/26

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Mon 3/30

4:20 pm-4:35 pm

Nonstop0h 15m

$288

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 3/25

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Mon 3/30

4:30 pm-4:45 pm

Nonstop0h 15m

$288

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Sun 12/28

10:10 am-10:25 am

Nonstop0h 15m

Gustavia St Barthelemy

Mon 1/5

4:20 pm-4:35 pm

Nonstop0h 15m

$288

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 12/5

11:05 am-11:20 am

Nonstop0h 15m

Gustavia St Barthelemy

Mon 12/8

5:30 pm-5:45 pm

Nonstop0h 15m

$288

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 11/12

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Wed 11/19

4:25 pm-4:40 pm

Nonstop0h 15m

$288

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 12/26

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Sat 1/3

4:30 pm-4:45 pm

Nonstop0h 15m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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 $63). 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 October 10, 2025.

It’s typically best to fly out from Simpson Bay to Caribbean Islands in the morning. Doing so could potentially save you 18% 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 October 10, 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
8.1
Very good
186 reviews

Boarding

8.1

Entertainment

6.7

Food

6.8

Overall

8.1

Comfort

7.8

Crew

8.4

Reviews

1 / 11
10.0
Excellent

Boy,Sep 2025

POS - YYZ

The pasta need to be cut out and some more local dishes need to be serve .
Caribbean Airlines
8.1
Very good
186 reviews
Caribbean Airlines
8.1
Very good
186 reviews

Boarding

8.1

Entertainment

6.7

Food

6.8

Overall

8.1

Comfort

7.8

Crew

8.4

Reviews

1 / 11
10.0
Excellent

Boy,Sep 2025

POS - YYZ

The pasta need to be cut out and some more local dishes need to be serve .

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 Arajet, Winair, and Contour 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 $149 on Arajet. Other airlines that offer cheap prices include Copa Airlines from $159 and Winair from $174 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 - Willemstad Hato Int. 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 $156. While the most popular route (Simpson Bay Princess Juliana - Gustavia St Barthelemy) can be booked for $248 on average, our data indicates $158 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 $63). 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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Alternative routes for Simpson Bay to Caribbean Islands

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Top 4 airlines flying from Simpson Bay to Caribbean Islands

Discover the top 4 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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$184FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$187Average$336FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$198Average$279FlexibilityNo cancel feeOn-timeN/A
WinairCheapest$356Average$471FlexibilityNo cancel feeOn-timeN/A

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