JAX - SXM

$143 Find Cheap Flights from Jacksonville to Simpson Bay

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 4/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$359
Typical prices: $430-$580
JetBlue
Sat 5/30Thu 6/18
JAX - SXM • 1 stop
Cheapest one-way
$143
Delta
Mon 4/20
JAX - SXM • 1 stop
Top airlines
Cheapest • from $359 (round-trip)
Best reviews • 7.9 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 $300 (round-trip)
Shortest trip • 5h 55m (one-way)
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

Sat, May 30 - Thu, Jun 18
JetBlue Logo
6:14 am - 4:09 pm
JAX
-
SXM
9h 55m
1 stop
JetBlue Logo
3:02 pm - 11:59 pm
SXM
-
JAX
8h 57m
1 stop
$359JetBlue
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:20 am - 1:50 pm
JAX
-
SXM
7h 30m
1 stop
American Airlines Logo
2:53 pm - 12:21 am
SXM
-
JAX
9h 28m
1 stop
$375American Airlines
Fri, May 1 - Wed, May 6
American Airlines Logo
8:19 pm - 11:37 am
JAX
-
SXM
15h 18m
2 stops
American Airlines Logo
12:41 pm - 11:59 pm
SXM
-
JAX
11h 18m
1 stop
$380American Airlines
Fri, May 1 - Wed, May 6
American Airlines Logo
11:00 am - 11:37 am
JAX
-
SXM
24h 37m
1 stop
American Airlines Logo
2:21 pm - 11:59 pm
SXM
-
JAX
9h 38m
1 stop
$382American Airlines
Tue, Jun 30 - Mon, Jul 6
American Airlines Logo
9:57 am - 3:42 pm
JAX
-
SXM
5h 45m
1 stop
American Airlines Logo
2:46 pm - 10:50 am
SXM
-
JAX
20h 04m
1 stop
$383American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
8:26 pm - 1:27 pm
JAX
-
SXM
17h 01m
1 stop
American Airlines Logo
4:09 pm - 10:16 am
SXM
-
JAX
18h 07m
2 stops
$385American Airlines
Sat, May 30 - Thu, Jun 18
American Airlines Logo
7:57 pm - 1:50 pm
JAX
-
SXM
17h 53m
1 stop
American Airlines Logo
4:43 pm - 12:54 pm
SXM
-
JAX
20h 11m
2 stops
$386American Airlines
Thu, Jun 18 - Mon, Jun 22
American Airlines Logo
7:59 pm - 3:42 pm
JAX
-
SXM
19h 43m
2 stops
American Airlines Logo
1:40 pm - 11:20 am
SXM
-
JAX
21h 40m
1 stop
$387American Airlines
Sat, Jun 13 - Fri, Jun 19
JetBlue Logo
6:05 am - 4:16 pm
JAX
-
SXM
10h 11m
1 stop
JetBlue Logo
3:02 pm - 11:59 pm
SXM
-
JAX
8h 57m
1 stop
$450JetBlue
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
8:26 pm - 1:27 pm
JAX
-
SXM
17h 01m
1 stop
American Airlines Logo
2:22 pm - 12:14 am
SXM
-
JAX
9h 52m
1 stop
$457American 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 May.

Good to know

Low seasonMay
Cheapest flight$143
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 7% increase in price.
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 3 days, the lowest price for a flight from Jacksonville to Simpson Bay was $143 for a one-way ticket and $359 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?

    SkyTeam, and oneworld are the airline alliances operating flights between Jacksonville and Simpson Bay, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Jacksonville to Simpson Bay are Delta and JetBlue. With an average price for the route of $549 and an overall rating of 7.9, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $494 and an overall rating of 7.2.

  • 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 3 airlines serving 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.
7.9
DeltaOverall score based on 8293 reviews
7.9Comfort
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

Other than nearly three hour delay for maintenance issues, everything went smooth

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

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

Information on your arrival and departure airports