$567+ Cheap flights from Jacksonville, NC (OAJ) to Simpson Bay (SXM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — SXM
Feb 27 — Mar 61
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jacksonville to Simpson Bay
Cheapest flights from Jacksonville to Simpson BayExplore the most affordable flight options available from Jacksonville to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.
Explore the most affordable flight options available from Jacksonville to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:10 am
OAJ
- SXM
1 stop8h 11m
American Airlines
Thu 5/72:24 pm
SXM
- OAJ
1 stop9h 33m
American Airlines
Deal found 1/28![American Airlines logo]()
$567
This WestJet deal was found by Cheapflights users on 1/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:49 am
OAJ
- SXM
2 stops26h 28m
WestJet
Fri 2/64:20 pm
SXM
- OAJ
2 stops30h 22m
WestJet
Deal found 1/25![WestJet logo]()
$3,646
Find flight deals from Jacksonville to Simpson Bay
Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (OAJ) 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 January 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $567 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Jacksonville 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 January 28, 2026.
Use the filters below to find and compare flights from Jacksonville to Simpson Bay that are best for you.
Fly from
Jacksonville
Fly to
Simpson Bay
Route
Depart
Return
Price
JacksonvilleSimpson Bay
OAJ - SXM
OAJSXM
Jacksonville Albert J Ellis
Mon 5/4
5:10 am-1:21 pm
1 stop8h 11m
Simpson Bay Princess Juliana
Thu 5/7
2:24 pm-11:57 pm
1 stop9h 33m
$567
- Most accurate provider: When it comes to deals on Jacksonville, North Carolina-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville, North Carolina-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville, North Carolina-Simpson Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jacksonville, North Carolina-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 Jacksonville, North Carolina-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 Jacksonville to Simpson Bay
Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Jacksonville 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.
Related info for your journey
Find useful and relevant information for your journey from Jacksonville to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Simpson Bay?
Book flights to Simpson Bay if you plan to visit one of these locationsPhilipsburg