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Simpson Bay

$109+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 3/88:07 pm
JAX
-
SXM
1 stop17h 09m
American Airlines
Mon 3/164:28 pm
SXM
-
JAX
1 stop16h 35m
American Airlines
Deal found 1/27$295
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Wed 3/116:00 am
JAX
-
SXM
1 stop7h 16m
American Airlines
Sun 3/152:17 pm
SXM
-
JAX
2 stops18h 34m
American Airlines
Deal found 1/26$305
This American Airlines deal was found by Cheapflights users on 1/26. 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 5/247:59 pm
JAX
-
SXM
2 stops19h 32m
American Airlines
Wed 5/274:36 pm
SXM
-
JAX
1 stop16h 47m
American Airlines
Deal found 1/26$350
This American Airlines deal was found by Cheapflights users on 1/26. 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 3/126:00 am
JAX
-
SXM
1 stop7h 16m
American Airlines
Thu 3/194:28 pm
SXM
-
JAX
1 stop16h 35m
American Airlines
Deal found 1/26$413
This JetBlue deal was found by Cheapflights users on 1/27. 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 9/36:10 am
JAX
-
SXM
1 stop7h 18m
JetBlue
Mon 9/711:45 am
SXM
-
JAX
1 stop11h 07m
JetBlue
Deal found 1/27$449
This American Airlines deal was found by Cheapflights users on 1/24. 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.
Fri 3/137:01 am
JAX
-
SXM
1 stop7h 59m
American Airlines
Thu 3/194:28 pm
SXM
-
JAX
1 stop16h 35m
American Airlines
Deal found 1/24$461

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$595
Provider with most accurate pricing for Jacksonville-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Jacksonville-Simpson Bay Princess Juliana flights.
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From Jacksonville to Simpson Bay Princess Juliana
Search Deals
One-way flight from Jacksonville to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 27, 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

JAX - SXM

JAXSXM

Jacksonville

Wed 2/25

7:02 am-4:00 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 3/4

5:28 pm-11:59 pm

1 stop7h 31m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Mon 5/11

5:30 am-1:59 pm

1 stop8h 29m

Simpson Bay Princess Juliana

Fri 5/15

3:20 pm-12:02 am

1 stop8h 42m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 3/15

8:05 pm-11:29 am

1 stop15h 24m

Simpson Bay Princess Juliana

Thu 3/19

4:28 pm-9:03 am

1 stop16h 35m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Mon 3/23

5:30 am-1:54 pm

1 stop8h 24m

Simpson Bay Princess Juliana

Tue 3/31

12:55 pm-12:02 am

1 stop11h 07m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 4/12

6:00 am-3:20 pm

1 stop9h 20m

Simpson Bay Princess Juliana

Wed 4/15

2:24 pm-12:19 am

1 stop9h 55m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 4/22

6:00 am-11:37 am

1 stop5h 37m

Simpson Bay Princess Juliana

Wed 4/29

2:24 pm-12:19 am

1 stop9h 55m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 3/8

8:05 pm-11:29 am

1 stop15h 24m

Simpson Bay Princess Juliana

Mon 3/16

4:28 pm-9:03 am

1 stop16h 35m

$295

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 5/15

6:12 pm-11:37 am

2 stops17h 25m

$109

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 5/15

8:17 pm-11:20 am

3 stops39h 03m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Compare providers for flights from Jacksonville 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 Jacksonville to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*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 Jacksonville-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-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-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-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.

Cheapflights Insights

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

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 January 27, 2026.
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
7.9
Good
8,118 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

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
8,118 reviews
Delta
7.9
Good
8,118 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

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
11,197 reviews
Delta
7.9
Good
8,118 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.8

Overall

7.9

Boarding

8.1

Food

7.2

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 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 American Airlines and Delta fly from Jacksonville to Simpson Bay in about 7h 58m. The time it takes to get you to your destination can typically vary by up to 31m. 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 ($490), and Delta ($500) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that American Airlines is 24% 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.

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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$490Average$645FlexibilityNo cancel feeOn-time71%
DeltaCheapest$500Average$549FlexibilityNo cancel feeOn-timeN/A

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