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Simpson Bay

$132+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
Apr 15 — Apr 221
Tue 4/15
Tue 4/22
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Simpson Bay Princess Juliana are usually found in August or September, booked 7 days in advance, depart on a Sunday or Tuesday and return on a Monday

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 April 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Booking.com)

One-way from

$132
(Mytrip)

Popular in

November

Cheapest in

August

Average price

$639
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
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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 ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 10, 2025.

This Booking.com deal was found by Cheapflights users on 4/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/199:00 pmJAX - SXM
1 stop20h 06mFrontier
Mon 6/236:26 pmSXM - JAX
1 stop25h 34mFrontier
Deal found 4/9$342
This American Airlines deal was found by Cheapflights users on 4/9. 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 5/38:11 pmJAX - SXM
1 stop16h 49mAmerican Airlines
Sat 5/104:40 pmSXM - JAX
1 stop7h 12mAmerican Airlines
Deal found 4/9$499
This Mytrip deal was found by Cheapflights users on 4/9. 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.
Fri 5/164:19 pmJAX - SXM
2 stops21h 41mMultiple Airlines
Fri 5/233:05 pmSXM - JAX
2 stops29h 53mMultiple Airlines
Deal found 4/9$517
This United Airlines deal was found by Cheapflights users on 4/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/249:20 amJAX - SXM
1 stop27h 09mUnited Airlines
Sat 5/313:55 pmSXM - JAX
1 stop28h 12mUnited Airlines
Deal found 4/9$809
This Cheapflightsfares deal was found by Cheapflights users on 4/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/156:58 pmJAX - SXM
2 stops18h 48mWestJet
Sun 4/203:10 pmSXM - JAX
2 stops23h 22mWestJet
Deal found 4/9$3,896

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 April 10, 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

Thu 6/19

9:00 pm-5:06 pm

1 stop20h 06m

Simpson Bay Princess Juliana

Mon 6/23

6:26 pm-8:00 pm

1 stop25h 34m

$342

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sat 5/3

8:11 pm-1:00 pm

1 stop16h 49m

Simpson Bay Princess Juliana

Sat 5/10

4:40 pm-11:52 pm

1 stop7h 12m

$499

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 5/16

4:19 pm-2:00 pm

2 stops21h 41m

Simpson Bay Princess Juliana

Fri 5/23

3:05 pm-8:58 pm

2 stops29h 53m

$517

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sat 5/24

9:20 am-12:29 pm

1 stop27h 09m

Simpson Bay Princess Juliana

Sat 5/31

3:55 pm-8:07 pm

1 stop28h 12m

$809

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 4/24

5:34 pm-2:16 pm

2 stops20h 42m

Simpson Bay Princess Juliana

Sun 4/27

2:10 pm-12:55 pm

2 stops22h 45m

$3,942

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 5/1

7:07 pm-5:01 pm

1 stop21h 54m

$132

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 5/1

4:26 pm-2:00 pm

2 stops21h 34m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/8

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 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 far ahead should I book a flight from Jacksonville to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Jacksonville to Simpson Bay. Price data was last updated on April 4, 2025.

The best time to book flights from Jacksonville to Simpson Bay is 7 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 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 July is currently the most expensive (average of $675). 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.

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 April 10, 2025.
Read through reviews of airlines operating flights from Jacksonville to Simpson Bay, such as United Airlines, American Airlines and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,634 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,634 reviews
United Airlines
7.4
Good
8,634 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,634 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
WestJet
7.2
Good
2,802 reviews
United Airlines
7.4
Good
8,634 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Frontier
6.0
Okay
3,279 reviews
United Airlines
7.4
Good
8,634 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

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

    According to our current data, Frontier ($342), American Airlines ($499), and United Airlines ($809) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that Frontier is 43% 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 July is currently the most expensive (average of $675). 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

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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 April 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$357Average$676FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$442Average$620FlexibilityNo cancel feeOn-time71%

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