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Simpson Bay

$127+ 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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 74 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 June 12, 2025.

Round-trip from

$283
(Priceline)

One-way from

$127
(Frontier)

Popular in

November

Cheapest in

August

Average price

$650
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. 5% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/10. 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.
Fri 7/2511:21 amJAX - SXM
1 stop6h 00mFrontier
Fri 8/16:26 pmSXM - JAX
1 stop15h 54mFrontier
Deal found 6/10$283
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/2511:47 amJAX - SXM
2 stops26h 13mMultiple Airlines
Fri 8/13:05 pmSXM - JAX
2 stops28h 04mMultiple Airlines
Deal found 6/10$460
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/166:25 amJAX - SXM
1 stop8h 45mAmerican Airlines
Thu 11/205:00 pmSXM - JAX
1 stop7h 56mAmerican Airlines
Deal found 6/11$509
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 9/125:30 amJAX - SXM
1 stop8h 20mDelta
Wed 9/173:15 pmSXM - JAX
1 stop7h 08mDelta
Deal found 6/11$534

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 June 12, 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

Fri 7/25

11:21 am-5:21 pm

1 stop6h 00m

Simpson Bay Princess Juliana

Fri 8/1

6:26 pm-10:20 am

1 stop15h 54m

$283

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 7/25

11:47 am-2:00 pm

2 stops26h 13m

Simpson Bay Princess Juliana

Fri 8/1

3:05 pm-7:09 pm

2 stops28h 04m

$460

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 9/5

6:00 am-1:19 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Fri 9/12

2:45 pm-11:12 pm

1 stop8h 27m

$549

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Mon 7/7

5:10 am-1:56 pm

1 stop8h 46m

Simpson Bay Princess Juliana

Thu 7/10

3:21 pm-11:54 pm

1 stop8h 33m

$594

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Fri 6/20

11:21 am-5:16 pm

1 stop5h 55m

$127

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 8/6

6:10 am-1:56 pm

1 stop7h 46m

$278

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Wed 8/6

7:01 pm-1:45 pm

2 stops18h 44m

$303

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Thu 6/19

9:44 am-2:00 pm

3 stops28h 16m

$368

JacksonvilleSimpson Bay

JAX - SXM

JAXSXM

Jacksonville

Tue 6/17

3:50 pm-12:29 pm

3 stops20h 39m

$1,830

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 9, 2025.

The best time to book flights from Jacksonville to Simpson Bay is 74 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 March is currently the most expensive (average of $657). 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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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.
Frontier
5.9
Fair
3,295 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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, Frontier ($283), American Airlines ($509), and Delta ($534) offers the cheapest pricing from Jacksonville to Simpson Bay. Users have found that Frontier is 55% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Jacksonville to Simpson Bay one-way?

    The cheapest airlines for a one-way flight from Jacksonville to Simpson Bay are Frontier ($127), Delta ($278), and American Airlines ($303).

  • 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 $657). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$357Average$631FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$454Average$626FlexibilityNo cancel feeOn-time71%

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