HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$499+ Cheap flights from Jacksonville (JAX) 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jacksonville to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$529
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$560
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
Highest demand for flights based on searches. 6% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/28. 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 12/145:13 amJAX - SXM
1 stop7h 42mAmerican Airlines
Fri 12/193:20 pmSXM - JAX
1 stop8h 35mAmerican Airlines
Deal found 4/28$499
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:10 amJAX - SXM
1 stop7h 44mDelta
Mon 5/193:19 pmSXM - JAX
1 stop7h 48mDelta
Deal found 4/29$695
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/412:22 pmJAX - SXM
3 stops24h 53mMultiple Airlines
Sun 6/82:10 pmSXM - JAX
3 stops30h 50mMultiple Airlines
Deal found 4/28$865

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 May 1, 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 10/18

8:25 pm-3:10 pm

2 stops18h 45m

Simpson Bay Princess Juliana

Sat 10/25

4:10 pm-11:54 pm

1 stop7h 44m

$529

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 5/28

6:30 am-2:43 pm

1 stop8h 13m

Simpson Bay Princess Juliana

Wed 6/4

3:55 pm-8:07 pm

1 stop28h 12m

$546

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 5/14

5:10 am-1:54 pm

1 stop8h 44m

Simpson Bay Princess Juliana

Mon 5/19

3:19 pm-12:14 am

1 stop8h 55m

$695

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sun 5/11

9:30 am-2:00 pm

3 stops28h 30m

Simpson Bay Princess Juliana

Sun 5/18

2:10 pm-3:02 pm

2 stops24h 52m

$1,646

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Jacksonville-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 25, 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 $669). 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 May 1, 2025.
Read through reviews of airlines operating flights from Jacksonville to Simpson Bay, such as Delta, United Airlines 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
7,934 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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, American Airlines ($529), United Airlines ($546), and Delta ($695) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that American Airlines is 13% 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 $669). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$357Average$676FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$441Average$624FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.