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Simpson Bay

$267+ Cheap flights from Jacksonville (JAX) 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Jacksonville to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) 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 September 11, 2025.

Round-trip from

$434
(Priceline)

One-way from

$267
(Delta)

Popular in

November

Cheapest in

August

Average price

$499
From Jacksonville to Simpson Bay Princess Juliana
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One-way flight from Jacksonville to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Jacksonville to Simpson Bay

Cheapest flights from Jacksonville to Simpson Bay
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 September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:12 pmJAX - SXM
1 stop22h 26mJetBlue
Sat 11/14:49 pmSXM - JAX
1 stop17h 43mJetBlue
Deal found 9/10$434
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:08 amJAX - SXM
1 stop8h 30mJetBlue
Mon 11/35:44 pmSXM - JAX
1 stop27h 53mJetBlue
Deal found 9/11$466
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 12/77:00 amJAX - SXM
1 stop8h 25mAmerican Airlines
Sun 12/145:25 pmSXM - JAX
1 stop7h 34mAmerican Airlines
Deal found 9/10$564
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 11/307:14 pmJAX - SXM
2 stops18h 05mAmerican Airlines
Sun 12/73:20 pmSXM - JAX
2 stops19h 35mAmerican Airlines
Deal found 9/11$574
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 11/296:06 pmJAX - SXM
1 stop21h 16mAmerican Airlines
Sun 12/75:25 pmSXM - JAX
1 stop7h 34mAmerican Airlines
Deal found 9/11$577
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Sun 9/2811:03 amJAX - SXM
3 stops26h 57mMultiple Airlines
Sat 10/43:05 pmSXM - JAX
2 stops16h 49mMultiple Airlines
Deal found 9/11$582
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/258:26 pmJAX - SXM
2 stops17h 16mAmerican Airlines
Sat 11/14:24 pmSXM - JAX
1 stop7h 35mAmerican Airlines
Deal found 9/10$599
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/116:12 pmJAX - SXM
2 stops19h 25mAmerican Airlines
Sat 10/184:24 pmSXM - JAX
1 stop7h 35mAmerican Airlines
Deal found 9/11$629
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/236:12 pmJAX - SXM
2 stops21h 03mAmerican Airlines
Sun 10/264:24 pmSXM - JAX
1 stop7h 35mAmerican Airlines
Deal found 9/10$659

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 September 11, 2025.
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

JAX - SXM

JAXSXM

Jacksonville

Sat 10/25

5:12 pm-3:38 pm

1 stop22h 26m

Simpson Bay Princess Juliana

Sat 11/1

4:49 pm-10:32 am

1 stop17h 43m

$434

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Mon 10/27

7:08 am-3:38 pm

1 stop8h 30m

Simpson Bay Princess Juliana

Mon 11/3

5:44 pm-8:37 pm

1 stop27h 53m

$466

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

5:30 am-2:56 pm

1 stop8h 26m

Simpson Bay Princess Juliana

Tue 1/27

1:45 pm-8:38 pm

1 stop7h 53m

$529

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

5:10 am-4:10 pm

2 stops10h 00m

Simpson Bay Princess Juliana

Tue 1/27

3:20 pm-12:14 am

1 stop9h 54m

$534

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 1/23

5:10 am-4:10 pm

2 stops10h 00m

Simpson Bay Princess Juliana

Fri 1/30

4:15 pm-8:33 am

2 stops17h 18m

$559

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 12/7

7:00 am-4:25 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Sun 12/14

5:25 pm-11:59 pm

1 stop7h 34m

$564

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 11/30

6:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Sun 12/7

3:20 pm-11:59 pm

1 stop9h 39m

$569

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

6:13 am-3:20 pm

1 stop8h 07m

$267

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

6:30 am-2:56 pm

1 stop7h 26m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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.

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Simpson Bay

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

Currently, September is the cheapest month in which you can book a flight from Jacksonville to Simpson Bay (average of $459). Flying from Jacksonville to Simpson Bay in March is currently the most expensive (average of $652). 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 Jacksonville 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 September 11, 2025.
Read through reviews of airlines operating flights from Jacksonville to Simpson Bay, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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 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.

  • How long is the flight from Jacksonville to Simpson Bay?

    Airlines like JetBlue, Delta, and American Airlines fly from Jacksonville to Simpson Bay in about 8h 26m. The time it takes to get you to your destination can typically vary by up to 14h. Jacksonville and Simpson Bay are separated by a distance of 1448 mi. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($499), and Delta ($524) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that American Airlines is 23% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville 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 Jacksonville to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Jacksonville to Simpson Bay (average of $459). Flying from Jacksonville to Simpson Bay in March is currently the most expensive (average of $652). 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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Top 2 airlines flying from Jacksonville to Simpson Bay

Discover the top 2 airlines that operate flights from Jacksonville 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$499Average$654FlexibilityNo cancel feeOn-time71%
DeltaCheapest$524Average$676FlexibilityNo cancel feeOn-timeN/A

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