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Simpson Bay

$209+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Expedia deal was found by Cheapflights users on 10/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:08 amJAX - SXM
1 stop8h 30mJetBlue
Thu 11/135:44 pmSXM - JAX
1 stop25h 35mJetBlue
Deal found 10/27$453
This Priceline deal was found by Cheapflights users on 10/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:00 amJAX - SXM
1 stop8h 38mJetBlue
Wed 12/175:49 pmSXM - JAX
1 stop17h 47mJetBlue
Deal found 10/25$500
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:40 amJAX - SXM
1 stop29h 03mJetBlue
Tue 12/95:49 pmSXM - JAX
1 stop17h 03mJetBlue
Deal found 10/26$510
This American Airlines deal was found by Cheapflights users on 10/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amJAX - SXM
2 stops9h 25mAmerican Airlines
Wed 12/175:25 pmSXM - JAX
2 stops22h 28mAmerican Airlines
Deal found 10/25$574
This American Airlines deal was found by Cheapflights users on 10/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:01 amJAX - SXM
1 stop7h 59mAmerican Airlines
Thu 12/45:25 pmSXM - JAX
1 stop7h 34mAmerican Airlines
Deal found 10/25$599
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/46:14 pmJAX - SXM
2 stops18h 38mAmerican Airlines
Tue 12/95:25 pmSXM - JAX
2 stops19h 51mAmerican Airlines
Deal found 10/26$629
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 11/307:46 pmJAX - SXM
1 stop19h 36mAmerican Airlines
Sun 12/75:25 pmSXM - JAX
2 stops19h 47mAmerican Airlines
Deal found 10/28$643
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/245:00 amJAX - SXM
1 stop7h 26mAmerican Airlines
Sun 12/281:39 pmSXM - JAX
1 stop7h 18mAmerican Airlines
Deal found 10/26$675

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$453
(Expedia)

One-way from

$209
(Mytrip)

Popular in

November

Cheapest in

August

Average price

$713
Provider with most accurate pricing for Jacksonville-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-Simpson Bay Princess Juliana flights.
Search Deals
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. 10% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 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 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 October 28, 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

Mon 11/10

7:08 am-4:38 pm

1 stop8h 30m

Simpson Bay Princess Juliana

Thu 11/13

5:44 pm-6:19 pm

1 stop25h 35m

$453

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 3/3

6:00 am-3:28 pm

1 stop8h 28m

Simpson Bay Princess Juliana

Tue 3/10

1:45 pm-11:32 pm

1 stop9h 47m

$467

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 2/1

8:10 pm-2:28 pm

1 stop17h 18m

Simpson Bay Princess Juliana

Wed 2/4

4:25 pm-7:15 pm

2 stops27h 50m

$478

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 12/4

10:40 am-4:43 pm

1 stop29h 03m

Simpson Bay Princess Juliana

Tue 12/9

5:49 pm-9:52 am

1 stop17h 03m

$510

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 2/1

6:00 pm-1:45 pm

2 stops18h 45m

Simpson Bay Princess Juliana

Wed 2/4

5:33 pm-1:51 pm

2 stops21h 18m

$524

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 3/31

7:55 am-2:20 pm

1 stop6h 25m

Simpson Bay Princess Juliana

Wed 4/8

2:35 pm-9:31 pm

1 stop6h 56m

$529

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sat 2/7

7:33 pm-1:45 pm

1 stop17h 12m

Simpson Bay Princess Juliana

Tue 2/17

3:40 pm-11:39 pm

1 stop8h 59m

$529

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 3/3

4:03 pm-12:40 pm

2 stops19h 37m

Simpson Bay Princess Juliana

Tue 3/10

2:30 pm-9:45 pm

1 stop7h 15m

$534

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

9:57 am-4:28 pm

1 stop5h 31m

Simpson Bay Princess Juliana

Tue 1/27

5:33 pm-9:26 am

1 stop16h 53m

$534

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 11/9

12:03 pm-2:15 pm

3 stops25h 12m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 15 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jacksonville-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Currently, August is the cheapest month in which you can book a flight from Jacksonville to Simpson Bay (average of $328). Flying from Jacksonville to Simpson Bay in November is currently the most expensive (average of $647). 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 October 28, 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
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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 and American Airlines fly from Jacksonville to Simpson Bay in about 8h 30m. The time it takes to get you to your destination can typically vary by up to 10h 15m. 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 25% 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, August is the cheapest month in which you can book a flight from Jacksonville to Simpson Bay (average of $328). Flying from Jacksonville to Simpson Bay in November is currently the most expensive (average of $647). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$499Average$657FlexibilityNo cancel feeOn-time71%
DeltaCheapest$524Average$611FlexibilityNo cancel feeOn-timeN/A

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