MCO - SXM

$117 Find Cheap Flights from Orlando 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 Orlando to Simpson Bay departing on 9/25. 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 Orlando 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 Orlando to Simpson Bay, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$317
Typical prices: $437-$615
JetBlue
Fri 10/2Fri 10/9
MCO - SXM • 1 stop
Cheapest non-stop
$391
Frontier
Sat 8/8Sat 8/15
MCO - SXM • Non-stop
Nonstop flights
Mon, Thu, Fri, Sat, Sun
You can fly direct with Southwest and Frontier. Average duration is 3h 20m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $317 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $442 (round-trip)
Shortest trip • 5h 15m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 91% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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 Orlando to Simpson Bay (MCO-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orlando 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 Orlando to Simpson Bay

Fri, Oct 2 - Fri, Oct 9
JetBlue Logo
8:55 am - 2:00 pm
MCO
-
SXM
5h 05m
1 stop
JetBlue Logo
1:45 pm - 10:09 pm
SXM
-
MCO
8h 24m
1 stop
$317JetBlue
Fri, Oct 2 - Sat, Oct 10
JetBlue Logo
8:55 am - 2:00 pm
MCO
-
SXM
5h 05m
1 stop
JetBlue Logo
1:45 pm - 10:09 pm
SXM
-
MCO
8h 24m
1 stop
$350JetBlue
Sat, Aug 15 - Sat, Aug 22
Multiple Airlines Logo
8:05 am - 11:30 am
MCO
-
SXM
3h 25mnonstop
Multiple Airlines Logo
1:42 pm - 10:16 pm
SXM
-
MCO
8h 34m
1 stop
$367Multiple Airlines
Fri, Oct 2 - Fri, Oct 9
JetBlue Logo
8:55 am - 2:00 pm
MCO
-
SXM
5h 05m
1 stop
JetBlue Logo
1:45 pm - 10:09 pm
SXM
-
MCO
8h 24m
1 stop
$377JetBlue
Sat, Aug 15 - Sat, Aug 22
JetBlue Logo
9:55 am - 12:37 pm
MCO
-
SXM
26h 42m
1 stop
JetBlue Logo
1:42 pm - 10:16 pm
SXM
-
MCO
8h 34m
1 stop
$383JetBlue
Sat, Aug 8 - Sat, Aug 15
Frontier Logo
8:05 am - 11:30 am
MCO
-
SXM
3h 25mnonstop
Frontier Logo
12:43 pm - 4:13 pm
SXM
-
MCO
3h 30mnonstop
$391Frontier
Fri, Aug 14 - Thu, Aug 20
Delta Logo
6:15 am - 1:53 pm
MCO
-
SXM
7h 38m
1 stop
Delta Logo
3:18 pm - 11:05 pm
SXM
-
MCO
7h 47m
1 stop
$401Delta
Mon, Aug 24 - Tue, Aug 25
American Airlines Logo
6:00 am - 1:22 pm
MCO
-
SXM
7h 22m
1 stop
American Airlines Logo
2:22 pm - 11:33 pm
SXM
-
MCO
9h 11m
1 stop
$411American Airlines
Wed, Sep 16 - Sun, Sep 20
JetBlue Logo
6:00 pm - 2:00 pm
MCO
-
SXM
20h 00m
1 stop
JetBlue Logo
3:05 pm - 9:35 pm
SXM
-
MCO
6h 30m
1 stop
$412JetBlue
Mon, Aug 24 - Tue, Aug 25
American Airlines Logo
9:59 am - 3:39 pm
MCO
-
SXM
5h 40m
1 stop
American Airlines Logo
4:39 pm - 2:12 pm
SXM
-
MCO
21h 33m
2 stops
$416American Airlines
Booking Insights

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

Get data-powered insights and trends into flights from Orlando 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 Orlando Airport 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 Orlando Airport to Simpson Bay departing in October.

What’s the cheapest day of the week to fly from Orlando to Simpson Bay?

The average price of all round-trip flights from Orlando Airport to Simpson Bay clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Simpson Bay on a Tuesday and more expensive on a Friday. On your return trip to Orlando, you should consider flying back on a Saturday, and avoid Tuesdays for better deals.

What is the cheapest month to fly from Orlando Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Airport 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 Orlando Airport to Simpson Bay is September, where tickets cost $419 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $734 and $692 respectively.

Can I save money by flying with a layover from Orlando Airport to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $585, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Orlando Airport to Simpson Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Orlando Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Orlando Airport to Simpson Bay, you should book around 4 weeks before departure, which saves you about 47% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$117
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Orlando to Simpson Bay

When to book flights from Orlando to Simpson Bay

Are your dates flexible? Find out the best times to travel from Orlando 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 Orlando to Simpson Bay flights

  • What is the cheapest flight from Orlando Airport to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Orlando Airport to Simpson Bay was $117 for a one-way ticket and $317 for a round-trip.

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

    Yes

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

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

  • Which airlines offer Wi-Fi service onboard planes from Orlando to Simpson Bay?

    JetBlue, and American Airlines offer inflight Wi-Fi service on the Orlando to Simpson Bay flight route.

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Orlando to Simpson Bay flight route.

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

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

  • On which days can I fly direct from Orlando to Simpson Bay?

    There are nonstop flights from Orlando to Simpson Bay on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Orlando to Simpson Bay are Southwest and Delta. With an average price for the route of $619 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $488 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Orlando 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 Orlando to Simpson Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Orlando 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 Orlando 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 Orlando with another airline. Booking your flights between Orlando 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 Orlando 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 Orlando up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Orlando Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $254 or less one-way and $555 or less round-trip.

Prefer to fly direct from Orlando to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Orlando to Simpson Bay Princess Juliana.
Find which airlines fly direct from Orlando Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Orlando to Simpson Bay Princess Juliana

Monday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Frontier,Southwest

Frontier,Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Orlando

Monday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Frontier,Southwest

Frontier,Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 5 airlines serving from Orlando to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Orlando 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 Orlando 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
SouthwestOverall score based on 4246 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Kayak could’ve posted the correct gate number. Almost missed my flight.

8.0 ExcellentValerie, Jun 2026
MCO - ATL
Read more Southwest reviews

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Clean planes and not take my comfort class seat away.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Flight delayed for people who “should’nt have gotten thru tsa” had to look for their bags took two hours With no explanation had never happened Poorly handled

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was great. Smooth flight, comfortable, left on time and landed on time.

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

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

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

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

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Flight got delayed for 5 hours no good explanation was offered ;(

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

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

Information on your arrival and departure airports