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Caribbean Islands

$151+ 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 12/28. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — SJU
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 August 21, 2025.

Round-trip from

$249
(Copa Airlines)

One-way from

$151
(Mytrip)

Popular in

December

Cheapest in

June

Average price

$174
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. 12% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 21, 2025.

This Copa Airlines deal was found by Cheapflights users on 8/19. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:24 pmSXM - SDQ
1 stop10h 01mCopa Airlines
Sat 10/256:24 pmSDQ - SXM
1 stop17h 07mCopa Airlines
Deal found 8/19$249
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2310:10 amSXM - SBH
Nonstop0h 15mWinair
Sun 8/245:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 8/19$274
This Expedia deal was found by Cheapflights users on 8/18. 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.
Thu 9/115:35 pmSXM - SDQ
Nonstop1h 30mArajet
Sun 10/56:03 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 8/18$278
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/39:17 amSXM - SJU
1 stop4h 48mMultiple Airlines
Thu 9/45:50 pmSJU - SXM
1 stop17h 36mMultiple Airlines
Deal found 8/20$281
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:00 amSXM - SBH
Nonstop0h 15mWinair
Thu 9/45:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 8/20$283
This SmartFares deal was found by Cheapflights users on 8/20. 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.
Thu 9/49:00 amSXM - SBH
Nonstop0h 15mWinair
Thu 9/254:15 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 8/20$284
This Gotogate deal was found by Cheapflights users on 8/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2110:10 amSXM - SBH
Nonstop0h 15mWinair
Thu 8/215:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 8/20$285
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Thu 9/115:35 pmSXM - SDQ
Nonstop1h 30mArajet
Wed 10/86:45 amSDQ - SXM
Nonstop1h 27mArajet
Deal found 8/18$296
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Thu 9/115:35 pmSXM - SDQ
Nonstop1h 30mArajet
Thu 9/183:03 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 8/18$297
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/148:35 pmSXM - SDQ
Nonstop1h 30mArajet
Sun 10/56:03 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 8/18$300
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Wed 9/109:17 amSXM - SDQ
Nonstop1h 30mArajet
Sun 9/216:03 pmSDQ - SXM
Nonstop1h 27mArajet
Deal found 8/18$302
This Winair deal was found by Cheapflights users on 8/19. 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.
Fri 12/1210:10 amSXM - SBH
Nonstop0h 15mWinair
Sun 12/214:25 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 8/19$304

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 August 21, 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

Fri 9/12

12:25 pm-10:26 pm

1 stop10h 01m

Santo Domingo Las Americas

Sat 9/20

6:17 pm-11:26 am

1 stop17h 09m

$249

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Wed 10/15

12:24 pm-10:25 pm

1 stop10h 01m

Santo Domingo Las Americas

Sat 10/25

6:24 pm-11:31 am

1 stop17h 07m

$249

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Wed 9/10

12:25 pm-10:26 pm

1 stop10h 01m

Santo Domingo Las Americas

Thu 9/18

6:17 pm-11:26 am

1 stop17h 09m

$249

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Fri 10/17

12:24 pm-10:25 pm

1 stop10h 01m

Santo Domingo Las Americas

Tue 10/28

6:43 pm-11:31 am

1 stop16h 48m

$249

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Sun 9/14

8:35 pm-10:05 pm

Nonstop1h 30m

Santo Domingo Las Americas

Wed 9/17

6:45 am-8:12 am

Nonstop1h 27m

$278

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Thu 9/11

5:35 pm-7:05 pm

Nonstop1h 30m

Santo Domingo Las Americas

Sun 10/5

6:03 pm-7:30 pm

Nonstop1h 27m

$278

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Wed 9/3

9:17 am-2:05 pm

1 stop4h 48m

San Juan Luis Munoz Marin Intl

Thu 9/4

5:50 pm-11:26 am

1 stop17h 36m

$281

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Thu 9/4

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Thu 9/4

5:25 pm-5:40 pm

Nonstop0h 15m

$283

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Sat 1/10

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Sat 1/17

4:20 pm-4:35 pm

Nonstop0h 15m

$284

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Thu 9/25

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Thu 9/25

4:15 pm-4:30 pm

Nonstop0h 15m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

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, September is the cheapest month in which you can book a flight from Simpson Bay to Caribbean Islands (average of $254). Flying from Simpson Bay to Caribbean Islands in June is currently the most expensive (average of $339). 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 August 21, 2025.

When flying from Simpson Bay to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 21, 2025.
Read reviews from past customers who have flown Caribbean Airlines and American 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
171 reviews

Comfort

7.9

Crew

8.4

Overall

8.1

Boarding

8.1

Food

6.8

Entertainment

6.7

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
Caribbean Airlines
8.1
Very good
171 reviews
Caribbean Airlines
8.1
Very good
171 reviews

Comfort

7.9

Crew

8.4

Overall

8.1

Boarding

8.1

Food

6.8

Entertainment

6.7

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
American Airlines
7.2
Good
10,000 reviews
Caribbean Airlines
8.1
Very good
171 reviews

Comfort

7.9

Crew

8.4

Overall

8.1

Boarding

8.1

Food

6.8

Entertainment

6.7

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.

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 Copa Airlines, Winair, and Sunrise Airways fly from Simpson Bay to Caribbean Islands in about 15m. The time it takes to get you to your destination can typically vary by up to 9h 46m. The distance from Simpson Bay to Caribbean Islands is about 20 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $151 on Arajet. Other airlines that offer cheap prices include WorldTicket from $160 and Winair from $164 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 $130. While the most popular route (Simpson Bay Princess Juliana - Gustavia St Barthelemy) can be booked for $248 on average our data indicates $214 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, September is the cheapest month in which you can book a flight from Simpson Bay to Caribbean Islands (average of $254). Flying from Simpson Bay to Caribbean Islands in June is currently the most expensive (average of $339). 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 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$175FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$187Average$309FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$200Average$285FlexibilityNo cancel feeOn-timeN/A
WinairCheapest$357Average$478FlexibilityNo cancel feeOn-timeN/A

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