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Simpson Bay

$257+ 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
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$496
(Expedia)

One-way from

$257
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$739
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. 4% potential increase in price ($30 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 July 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 July 29, 2025.

This Expedia deal was found by Cheapflights users on 7/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/115:12 pmJAX - SXM
1 stop20h 03mJetBlue
Thu 9/182:35 pmSXM - JAX
1 stop20h 05mJetBlue
Deal found 7/28$496
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:30 amJAX - SXM
1 stop7h 05mDelta
Fri 12/54:00 pmSXM - JAX
1 stop7h 43mDelta
Deal found 7/27$509
This American Airlines deal was found by Cheapflights users on 7/27. 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 12/76:30 amJAX - SXM
1 stop8h 10mAmerican Airlines
Sun 12/144:45 pmSXM - JAX
2 stops16h 45mAmerican Airlines
Deal found 7/27$544
This Air Canada deal was found by Cheapflights users on 7/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/277:10 amJAX - SXM
2 stops31h 50mAir Canada
Mon 12/15:00 pmSXM - JAX
2 stops28h 10mAir Canada
Deal found 7/27$787
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2211:30 amJAX - SXM
1 stop27h 27mUnited Airlines
Sun 11/302:20 pmSXM - JAX
1 stop25h 18mUnited Airlines
Deal found 7/27$1,173

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 July 29, 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 9/11

5:12 pm-1:15 pm

1 stop20h 03m

Simpson Bay Princess Juliana

Thu 9/18

2:35 pm-10:40 am

1 stop20h 05m

$496

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 11/26

6:30 am-2:35 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Fri 12/5

4:00 pm-10:43 pm

1 stop7h 43m

$509

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sat 1/17

1:23 pm-3:20 pm

1 stop24h 57m

Simpson Bay Princess Juliana

Sat 1/24

4:15 pm-12:14 am

1 stop8h 59m

$542

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 11/27

7:10 am-4:00 pm

2 stops31h 50m

Simpson Bay Princess Juliana

Mon 12/1

5:00 pm-8:10 pm

2 stops28h 10m

$787

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Sat 11/22

11:30 am-3:57 pm

1 stop27h 27m

Simpson Bay Princess Juliana

Sun 11/30

2:20 pm-2:38 pm

1 stop25h 18m

$1,173

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

5:10 am-3:20 pm

2 stops9h 10m

$257

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 1/20

11:17 am-1:51 pm

3 stops25h 34m

$1,930

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 $655). 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 July 29, 2025.
Read through reviews of airlines operating flights from Jacksonville to Simpson Bay, such as Delta, United Airlines, and JetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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.
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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.
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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.
Air Canada
7.1
Good
9,822 reviews
Delta
8.0
Very good
7,977 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

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.

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

    According to our current data, JetBlue ($496), Delta ($509), and American Airlines ($542) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that JetBlue is 22% 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 $655). 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$377Average$631FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$458Average$631FlexibilityNo cancel feeOn-time71%

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