JAX - SXM

$203 Find Cheap Flights from Jacksonville to Simpson Bay - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Simpson Bay departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$375
Typical prices: $302-$603
American Airlines
Sun 8/30Thu 9/3
JAX - SXM • 1 stop
Cheapest one-way
$144
American Airlines
Sat 12/12
JAX - SXM • 2 stops
Top airlines
Cheapest • from $375 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Jacksonville and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $520 (round-trip)
Shortest trip • 5h 35m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jacksonville to Simpson Bay (JAX-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jacksonville to Simpson Bay

Sun, Aug 30 - Thu, Sep 3
American Airlines Logo
6:00 am - 3:39 pm
JAX
-
SXM
9h 39m
1 stop
American Airlines Logo
2:22 pm - 12:30 am
SXM
-
JAX
10h 08m
1 stop
$375American Airlines
Sun, Aug 30 - Thu, Sep 3
American Airlines Logo
6:12 pm - 1:22 pm
JAX
-
SXM
19h 10m
2 stops
American Airlines Logo
4:39 pm - 11:56 am
SXM
-
JAX
19h 17m
2 stops
$380American Airlines
Thu, Sep 10 - Thu, Sep 17
American Airlines Logo
7:45 am - 1:23 pm
JAX
-
SXM
5h 38m
1 stop
American Airlines Logo
2:23 pm - 11:59 pm
SXM
-
JAX
9h 36m
1 stop
$380American Airlines
Sun, Aug 30 - Thu, Sep 3
American Airlines Logo
6:30 am - 1:42 pm
JAX
-
SXM
7h 12m
1 stop
American Airlines Logo
4:39 pm - 11:56 am
SXM
-
JAX
19h 17m
2 stops
$380American Airlines
Sat, Sep 12 - Thu, Sep 17
JetBlue Logo
7:19 am - 2:00 pm
JAX
-
SXM
6h 41m
1 stop
JetBlue Logo
3:05 pm - 10:29 pm
SXM
-
JAX
7h 24m
1 stop
$382JetBlue
Sun, Sep 6 - Fri, Sep 11
JetBlue Logo
7:10 am - 12:37 pm
JAX
-
SXM
5h 27m
1 stop
JetBlue Logo
3:05 pm - 10:29 pm
SXM
-
JAX
7h 24m
1 stop
$382JetBlue
Sun, Aug 30 - Thu, Sep 3
JetBlue Logo
7:10 am - 12:37 pm
JAX
-
SXM
5h 27m
1 stop
JetBlue Logo
1:42 pm - 7:57 pm
SXM
-
JAX
6h 15m
1 stop
$385JetBlue
Sat, Jan 9 - Wed, Jan 13
United Airlines Logo
3:50 pm - 1:50 pm
JAX
-
SXM
21h 00m
2 stops
United Airlines Logo
2:52 pm - 10:00 am
SXM
-
JAX
20h 08m
1 stop
$586United Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
10:06 am - 10:04 am
JAX
-
SXM
23h 58m
2 stops
Multiple Airlines Logo
5:00 pm - 6:53 pm
SXM
-
JAX
25h 53m
3 stops
$857Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
8:55 pm - 1:54 pm
JAX
-
SXM
16h 59m
2 stops
Multiple Airlines Logo
5:00 pm - 6:53 pm
SXM
-
JAX
25h 53m
3 stops
$874Multiple Airlines
Booking Insights

KAYAK's insights & trends for Jacksonville to Simpson Bay flights

Get data-powered insights and trends into flights from Jacksonville to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Jacksonville to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Jacksonville to Simpson Bay departing in August.

Flight prices are typical for this route right now.

Flights to Simpson Bay from Jacksonville usually cost between $309 and $698 in August.
The lowest price found in the past 5 days was $375 on American Airlines (Aug 30-Sep 3).

What is the cheapest month to fly from Jacksonville to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jacksonville to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Jacksonville to Simpson Bay is May, where tickets cost $437 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $880 and $826 respectively.

Good to know

Low season

February

Cheapest flight

$203
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Jacksonville to Simpson Bay

When to book flights from Jacksonville to Simpson Bay

Are your dates flexible? Find out the best times to travel from Jacksonville to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Jacksonville to Simpson Bay

  • What is the cheapest flight from Jacksonville to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Jacksonville to Simpson Bay was $144 for a one-way ticket and $375 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Simpson Bay?

    A passport is required to fly from Jacksonville to Simpson Bay.

  • Which airports will I be using when flying from Jacksonville to Simpson Bay?

    Jacksonville airport is called Jacksonville and the only airport in Simpson Bay is Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Jacksonville to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jacksonville to Simpson Bay?

    oneworld is the only airline alliance operating flights between Jacksonville and Simpson Bay.

  • Which is the best airline for flights from Jacksonville to Simpson Bay, American Airlines or JetBlue?

    The two airlines most popular with KAYAK users for flights from Jacksonville to Simpson Bay are American Airlines and JetBlue. With an average price for the route of $550 and an overall rating of 7.1, American Airlines is the most popular choice. JetBlue is also a great choice for the route, with an average price of $480 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Jacksonville to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Jacksonville to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jacksonville to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Jacksonville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Jacksonville to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Jacksonville with another airline. Booking your flights between Jacksonville and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jacksonville to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Jacksonville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Jacksonville to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Jacksonville to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11841 reviews
7.9Crew
7.2Comfort
7.5Boarding
6.8Entertainment
6.4Food
Airline reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

10.0 ExcellentSergio, Jul 2026
MIA - DCA
Read more American Airlines reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

Baggage claim took too long and priority bags were not delivered first.

Delayed 4 hours from Charlotte to Nashville. Could have driven there faster. Information provided by AA was sparse.

Gate change was a little tough but it was a good flight otherwise

Great flight, great service but most of all- our luggage made the trip with us.,

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Not having an assigned seat until boarding and then having to check my bag.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Everything you need to know for your flight from Jacksonville to Simpson Bay

Information on your arrival and departure airports