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Find cheap flights from Simpson Bay to Caribbean Islands from $115

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to Caribbean Islands departing on 6/21. 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
0 bags
Wed 6/12
Wed 6/19

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Santo Domingo
Santo Domingononstop$235
Kingston
Kingston1 stop$721
Bridgetown
Bridgetown1 stop$415
Castries
Castries1 stop$711
Willemstad
Willemstadnonstop$231
St. John's
St. John's1 stop$336

Good to know

Low season

November

High season

December

Cheapest flight

$115
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Simpson Bay to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Simpson Bay to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Simpson Bay 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 Simpson Bay to Caribbean Islands?

    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 Caribbean Islands with an airline and back to Simpson Bay with another airline.

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

    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 Caribbean Islands from Simpson Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Simpson Bay to the following destinations at these prices or less: Willemstad $245 one-way - $234 round-trip; Port of Spain $299 one-way - $527 round-trip; Gustavia $182 one-way - $284 round-trip

Top 3 airlines serving from Simpson Bay to Caribbean Islands

 
Need help choosing which airline to fly with from Simpson Bay to Caribbean Islands? 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
Caribbean AirlinesOverall score based on 186 reviews
6.7Entertainment
8.2Boarding
6.7Food
8.3Crew
7.6Comfort
Airline reviews

There was no music on the flights unless you came with your headset.

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

Flight was delayed three hours waiting for the flight crew, even though the plane was at the gate for the scheduled departure

The absolute worst. Our flight from Madrid to Charlotte was delayed nearly 2hrs which cost us to miss our connecting flight. The only availability was to either separate my party of four (two being children) several other locations to reach our final destination. The other was drop us off at entirely different location we never intended on going. Thus resulting in us driving a rental 2 hrs to our original final destination. On top of that the flight from Madrid was uncomfortable and some staff were extremely rude.

The flight was awful. Apart from the flight delays, it was bumpy and uncomfortable. I feared for my life.

My previous flight was late and did not connect properly. The gate was closed and I missed this flight.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Poor on time performance. Flight was delayed due to a lightbulb. No updates from the pilot. Plane was dirty and hot, AC didn't work well.

just overall disappointing, not a treat to travel these days....paying for Main Cabin Extra was not worth it.

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

First of all , lucky I caught our flight changes and we actually flew into chicago then Fort Myers

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Book cheap flights from Simpson Bay to Caribbean Islands

Recent round-trip flight deals

6/14Fri
nonstop
1h 04mSXM-SJU
6/16Sun
nonstop
1h 10mSJU-SXM
$179
7/12Fri
nonstop
1h 03mSXM-SJU
7/14Sun
nonstop
1h 10mSJU-SXM
$209
6/23Sun
nonstopJetair Caribbean
1h 35mSXM-CUR
6/28Fri
nonstopJetair Caribbean
1h 35mCUR-SXM
$231
6/12Wed
nonstopArajet
1h 30mSXM-SDQ
6/26Wed
nonstopArajet
1h 25mSDQ-SXM
$235
10/24Thu
nonstopSilver Airways
1h 10mSXM-SJU
11/3Sun
nonstopSilver Airways
1h 10mSJU-SXM
$241
7/24Wed
nonstopArajet
1h 30mSXM-SDQ
7/31Wed
nonstopArajet
1h 25mSDQ-SXM
$267
8/9Fri
nonstopWinair
0h 15mSXM-SBH
8/18Sun
nonstopWinair
0h 15mSBH-SXM
$303
7/9Tue
nonstopWinair
0h 15mSXM-SBH
7/14Sun
nonstopWinair
0h 15mSBH-SXM
$304
10/23Wed
1 stopAmerican Airlines
22h 46mSXM-SJU
10/31Thu
1 stopAmerican Airlines
8h 33mSJU-SXM
$568
10/23Wed
1 stopAmerican Airlines
22h 46mSXM-SJU
10/30Wed
1 stopAmerican Airlines
8h 33mSJU-SXM
$590

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Recent one-way flight deals

6/21Fri
nonstopFrontier
1h 04mSXM-SJU
$115
7/21Sun
nonstopArajet
1h 30mSXM-SDQ
$140
6/9Sun
nonstopArajet
1h 30mSXM-SDQ
$145
6/11Tue
nonstopSilver Airways
1h 10mSXM-SJU
$173
6/2Sun
nonstopWinair
0h 15mSXM-SBH
$177
7/1Mon
nonstopWinair
0h 15mSXM-SBH
$183
5/19Sun
nonstopSilver Airways
1h 10mSXM-SJU
$237
7/2Tue
2 stopsCaribbean Airlines
16h 15mSXM-KIN
$306
7/2Tue
nonstopCaribbean Airlines
2h 30mSXM-KIN
$335
7/2Tue
1 stopAmerican Airlines
30h 04mSXM-KIN
$496

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Last minute flights from Simpson Bay to Caribbean Islands

Last minute flight, train and bus deals

5/15Wed
nonstop
1h 30mSXM-SDQ
5/16Thu
multi-stop
21h 58mSDQ-SXM
$442
5/15Wed
multi-stopSpirit Airlines
11h 32mSXM-SDQ
5/16Thu
multi-stopSpirit Airlines
30h 27mSDQ-SXM
$458
5/15Wed
multi-stopSpirit Airlines
11h 32mSXM-SDQ
5/16Thu
multi-stopSpirit Airlines
21h 58mSDQ-SXM
$475
5/15Wed
multi-stopAmerican Airlines
8h 25mSXM-SJU
5/22Wed
multi-stopAmerican Airlines
16h 46mSJU-SXM
$523
5/15Wed
multi-stop
6h 17mSXM-SJU
5/21Tue
multi-stop
12h 45mSJU-SXM
$525
5/17Fri
nonstopWinair
1h 00mSXM-DOM
5/19Sun
multi-stopWinair
12h 50mDOM-SXM
$573
5/15Wed
multi-stopSpirit Airlines
11h 44mSXM-SDQ
5/16Thu
multi-stopSpirit Airlines
30h 27mSDQ-SXM
$592
5/17Fri
nonstopWinair
1h 00mSXM-DOM
5/19Sun
multi-stopWinair
6h 50mDOM-SXM
$607
5/15Wed
multi-stopSpirit Airlines
11h 26mSXM-SJU
5/21Tue
multi-stopSpirit Airlines
12h 45mSJU-SXM
$607
5/15Wed
multi-stopJetBlue
11h 01mSXM-SJU
5/21Tue
multi-stopJetBlue
10h 37mSJU-SXM
$1,887

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Simpson Bay - Caribbean Islands Flights

Departure:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Caribbean Islands - Simpson Bay

Cabin classes:

$1,427
$921
$1,304
$113

Browse origins:

  • Flights » 
  • Simpson Bay