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Simpson Bay

$130+ Cheap flights from Orlando (MCO) to Simpson Bay (SXM)

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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SXM
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Simpson Bay Princess Juliana are usually found in June or August, booked 64 days in advance, depart on a Wednesday or Monday and return on a Thursday

Find flight deals from Orlando to Simpson Bay

Cheapest flights from Orlando to Simpson Bay
Explore the most affordable flight options available from Orlando to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/226:30 amMCO - SXM
1 stop6h 45mSpirit Airlines
Mon 11/243:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$362
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/176:30 amMCO - SXM
1 stop6h 45mSpirit Airlines
Fri 11/213:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$364
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Mon 12/16:45 amMCO - SXM
1 stop6h 30mSpirit Airlines
Sat 12/63:15 pmSXM - MCO
1 stop17h 30mSpirit Airlines
Deal found 10/20$368
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/207:50 pmMCO - SXM
1 stop17h 25mSpirit Airlines
Mon 11/243:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$370
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/226:30 amMCO - SXM
1 stop6h 45mSpirit Airlines
Fri 11/283:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$371
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/216:30 amMCO - SXM
1 stop6h 45mSpirit Airlines
Mon 11/243:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$374
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Tue 11/1810:40 amMCO - SXM
2 stops32h 12mMultiple Airlines
Sat 11/223:20 pmSXM - MCO
1 stop9h 21mMultiple Airlines
Deal found 10/21$377
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/246:45 amMCO - SXM
1 stop6h 30mSpirit Airlines
Fri 11/283:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$381
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Tue 11/1810:40 amMCO - SXM
2 stops32h 12mMultiple Airlines
Mon 11/243:20 pmSXM - MCO
1 stop17h 31mMultiple Airlines
Deal found 10/21$383
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/207:50 pmMCO - SXM
1 stop17h 25mSpirit Airlines
Fri 11/283:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$389
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/216:30 amMCO - SXM
1 stop6h 45mSpirit Airlines
Fri 11/283:20 pmSXM - MCO
1 stop17h 31mSpirit Airlines
Deal found 10/21$393

Cheap flight deals from Orlando to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$362
(Kiwi.com)

One-way from

$130
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$503
Provider with most accurate pricing for Orlando-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando-Simpson Bay Princess Juliana flights.
Search Deals
From Orlando to Simpson Bay Princess Juliana
Search Deals
One-way flight from Orlando to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Simpson Bay 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 22, 2025.
Use the filters below to find and compare flights from Orlando Airport to Simpson Bay that are best for you.

Fly from

Orlando

Fly to

Simpson Bay

Route

Depart

Return

Price

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Sat 11/22

6:30 am-2:15 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Mon 11/24

3:20 pm-7:51 am

1 stop17h 31m

$362

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Tue 11/18

10:40 am-7:52 pm

2 stops32h 12m

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-11:41 pm

1 stop9h 21m

$377

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Mon 11/24

6:45 am-2:15 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Fri 11/28

3:20 pm-7:51 am

1 stop17h 31m

$381

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Thu 11/20

7:50 pm-2:15 pm

1 stop17h 25m

Simpson Bay Princess Juliana

Fri 11/28

3:20 pm-7:51 am

1 stop17h 31m

$389

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Fri 11/21

6:30 am-2:15 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Fri 11/28

3:20 pm-7:51 am

1 stop17h 31m

$393

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Thu 12/4

7:34 pm-2:10 pm

1 stop17h 36m

Simpson Bay Princess Juliana

Thu 12/11

11:30 am-9:00 pm

2 stops34h 30m

$403

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Mon 11/24

6:45 am-2:15 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Sat 11/29

3:20 pm-11:41 pm

1 stop9h 21m

$404

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Sat 11/22

6:30 am-2:15 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sat 11/29

3:20 pm-11:41 pm

1 stop9h 21m

$404

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Mon 11/24

6:45 am-2:15 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Thu 11/27

11:30 am-11:59 pm

2 stops37h 29m

$410

OrlandoSimpson Bay

MCO - SXM

MCOSXM

Orlando

Thu 11/20

6:30 am-11:28 am

2 stops27h 58m

Simpson Bay Princess Juliana

Mon 11/24

3:20 pm-7:51 am

1 stop17h 31m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 21 results
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Compare providers for flights from Orlando to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Orlando Airport-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando Airport-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Orlando to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Orlando 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 Orlando Airport to Simpson Bay

How far ahead should I book a flight from Orlando Airport to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Simpson Bay. Price data was last updated on October 17, 2025.

The best time to book flights from Orlando Airport to Simpson Bay is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Orlando Airport to Simpson Bay?

Currently, August is the cheapest month in which you can book a flight from Orlando Airport to Simpson Bay (average of $171). Flying from Orlando Airport to Simpson Bay in December is currently the most expensive (average of $412). 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.

How much does it cost to fly round-trip from Orlando Airport to Simpson Bay?

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated October 22, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and Spirit Airlines from Orlando Airport to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,979 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,979 reviews
Delta
7.9
Good
7,979 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,028 reviews
Delta
7.9
Good
7,979 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,097 reviews
Delta
7.9
Good
7,979 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.8
Fair
3,130 reviews
Delta
7.9
Good
7,979 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Boarding

8.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Simpson Bay. 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 into for flights to Simpson Bay from Orlando?

    Simpson Bay Princess Juliana (SXM), located 0.5 mi from the city center, is the airport you fly into when you book flights from Orlando to Simpson Bay. 4 airlines have flights to Princess Juliana from Orlando on a regular basis. Booking flights from Orlando to Simpson Bay Princess Juliana should not be difficult; the airport handles an average of 0 inbound flights from Orlando per day.

  • How long is the flight from Orlando Airport to Simpson Bay?

    Departing from Orlando Airport to Simpson Bay will take you 6h 45m. The distance from Orlando Airport to Simpson Bay is about 1357 mi.

  • What are the cheapest airlines flying from Orlando Airport to Simpson Bay round-trip?

    Flying on Frontier is currently your cheapest option to Simpson Bay, with prices starting at $220. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Delta, with the lowest prices starting at $264 and $295, respectively. Frontier is currently priced 58% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Orlando to Simpson Bay 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 Orlando Airport to Simpson Bay?

    Currently, August is the cheapest month in which you can book a flight from Orlando Airport to Simpson Bay (average of $171). Flying from Orlando Airport to Simpson Bay in December is currently the most expensive (average of $412). 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.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top 4 airlines flying from Orlando to Simpson Bay

Discover the top 4 airlines that operate flights from Orlando to Simpson Bay. 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 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$220Average$353FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$264Average$365FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$527FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$495Average$603FlexibilityNo cancel feeOn-time71%

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