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Caribbean Islands

$138+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Round-trip from

$283
(Orbitz)

One-way from

$138
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$259
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. 14% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Travelocity deal was found by Cheapflights users on 4/29. 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.
Wed 4/309:00 amSXM - SBH
Nonstop0h 15mWinair
Thu 5/84:20 pmSBH - SXM
Nonstop0h 15mWinair
Deal found 4/29$283
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/96:11 pmSXM - SJU
Nonstop1h 04mFrontier
Mon 5/193:55 pmSJU - SXM
Nonstop1h 06mFrontier
Deal found 4/29$283
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/912:18 pmSXM - SJU
1 stop9h 58mMultiple Airlines
Mon 5/193:55 pmSJU - SXM
Nonstop1h 06mMultiple Airlines
Deal found 4/29$288
This SmartFares deal was found by Cheapflights users on 4/29. 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.
Mon 11/33:50 pmSXM - DOM
2 stops2h 45mWinair
Mon 11/107:05 pmDOM - SXM
Nonstop0h 45mWinair
Deal found 4/29$385
This Winair deal was found by Cheapflights users on 4/29. 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.
Sat 8/167:10 amSXM - CUR
Nonstop2h 15mWinair
Sat 9/1312:35 pmCUR - SXM
Nonstop2h 15mWinair
Deal found 4/29$399
This Orbitz deal was found by Cheapflights users on 4/29. 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.
Fri 11/79:55 amSXM - DOM
3 stops5h 55mMultiple Airlines
Fri 11/147:35 pmDOM - SXM
Nonstop0h 45mMultiple Airlines
Deal found 4/29$464
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1212:40 pmSXM - SJU
1 stop13h 41mJetBlue
Sun 6/158:30 pmSJU - SXM
1 stop16h 58mJetBlue
Deal found 4/29$519
This Orbitz deal was found by Cheapflights users on 4/29. 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.
Fri 11/79:55 amSXM - DOM
3 stops5h 55mHahn Air
Fri 11/144:20 pmDOM - SXM
2 stops3h 30mHahn Air
Deal found 4/29$528
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1212:40 pmSXM - SDQ
1 stop11h 54mJetBlue
Tue 6/242:05 amSDQ - SXM
1 stop11h 23mJetBlue
Deal found 4/29$592
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/2410:25 amSXM - KIN
Nonstop2h 30mMultiple Airlines
Thu 5/291:34 pmKIN - SXM
1 stop23h 26mMultiple Airlines
Deal found 4/29$643
This FlightHub deal was found by Cheapflights users on 4/29. 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.
Fri 5/911:35 amSXM - SJU
2 stops26h 10mCaribbean Airlines
Thu 5/153:15 pmSJU - SXM
3 stops19h 35mCaribbean Airlines
Deal found 4/29$739
This FlightHub deal was found by Cheapflights users on 4/28. 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.
Sat 8/166:10 pmSXM - CUR
2 stops20h 23mMultiple Airlines
Sat 9/136:05 pmCUR - SXM
Nonstop2h 15mMultiple Airlines
Deal found 4/28$777

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 April 30, 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

Thu 5/22

9:00 am-9:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Tue 5/27

5:50 pm-6:05 pm

Nonstop0h 15m

$283

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Sun 5/11

12:18 pm-10:16 pm

1 stop9h 58m

San Juan Luis Munoz Marin Intl

Mon 5/19

3:55 pm-5:01 pm

Nonstop1h 06m

$288

Simpson BayRoseau

SXM - DOM

SXMDOM

Simpson Bay Princess Juliana

Wed 6/11

7:00 am-8:05 am

Nonstop1h 05m

Roseau Douglas–Charles

Fri 6/27

7:45 pm-8:50 pm

Nonstop1h 05m

$397

Simpson BayWillemstad

SXM - CUR

SXMCUR

Simpson Bay Princess Juliana

Sat 8/16

7:10 am-9:25 am

Nonstop2h 15m

Willemstad Hato Int.

Sat 9/13

12:35 pm-2:50 pm

Nonstop2h 15m

$399

Simpson BayRoseau

SXM - DOM

SXMDOM

Simpson Bay Princess Juliana

Wed 6/11

4:45 pm-6:35 pm

1 stop1h 50m

Roseau Douglas–Charles

Fri 6/27

4:20 pm-7:50 pm

2 stops3h 30m

$485

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Thu 6/12

12:40 pm-2:21 am

1 stop13h 41m

San Juan Luis Munoz Marin Intl

Sun 6/15

8:30 pm-1:28 pm

1 stop16h 58m

$519

Simpson BayRoseau

SXM - DOM

SXMDOM

Simpson Bay Princess Juliana

Fri 5/30

9:55 am-3:50 pm

3 stops5h 55m

Roseau Douglas–Charles

Tue 6/3

1:40 pm-9:10 am

1 stop19h 30m

$554

Simpson BaySanto Domingo

SXM - SDQ

SXMSDQ

Simpson Bay Princess Juliana

Thu 6/12

12:40 pm-12:34 am

1 stop11h 54m

Santo Domingo Las Americas

Tue 6/24

2:05 am-1:28 pm

1 stop11h 23m

$592

Simpson BayKingston

SXM - KIN

SXMKIN

Simpson Bay Princess Juliana

Sat 5/24

10:25 am-11:55 am

Nonstop2h 30m

Kingston Norman Manley

Thu 5/29

1:34 pm-2:00 pm

1 stop23h 26m

$643

Simpson BaySan Juan

SXM - SJU

SXMSJU

Simpson Bay Princess Juliana

Sat 5/10

6:10 pm-2:00 pm

1 stop19h 50m

San Juan Luis Munoz Marin Intl

Thu 5/15

3:15 pm-10:50 am

3 stops19h 35m

$699

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 45 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 December is currently the most expensive (average of $336). 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 April 30, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 30, 2025.
Get a feel of what it's like to fly with Caribbean Airlines, Copa Airlines and United Airlines from Simpson Bay to Caribbean Islands by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Caribbean Airlines
8.2
Very good
151 reviews
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Copa Airlines
7.5
Good
1,411 reviews
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
United Airlines
7.4
Good
8,696 reviews
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
JetBlue
7.3
Good
2,922 reviews
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
American Airlines
7.2
Good
10,000 reviews
Caribbean Airlines
8.2
Very good
151 reviews

Entertainment

6.8

Comfort

7.9

Crew

8.5

Overall

8.2

Boarding

8.2

Food

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.

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.

  • 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 $138 on Arajet. Other airlines that offer cheap prices include Frontier from $164 and Silver Airways from $167 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 most reliable airlines from Simpson Bay to Caribbean Islands?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Simpson Bay to Caribbean Islands on time: JetBlue (82%), Silver Airways (82%), United Airlines (82%).

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

    Looking at all options, your cheapest flight can be booked for $171. While the most popular route (Simpson Bay Princess Juliana - Gustavia St Barthelemy) can be booked for $248 on average our data indicates $277 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 December is currently the most expensive (average of $336). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$103Average$155FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$190Average$271FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$212Average$271FlexibilityNo cancel feeOn-timeN/A
WinairCheapest$498Average$552FlexibilityNo cancel feeOn-timeN/A
Caribbean AirlinesCheapest$575Average$604FlexibilityNo cancel feeOn-timeN/A

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