$156 Find Cheap Flights from Simpson Bay to Caribbean Islands

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 10/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Caribbean Islands.
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Flight Deals

Cheap Flights from Simpson Bay to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingononstop$243
Oranjestad
Oranjestad1 stop$581
Kingston
Kingston2 stops$617
Port of Spain
Port of Spain1 stop$511
Bridgetown
Bridgetown1 stop$425
Willemstad
Willemstadnonstop$381
Castries
Castries2 stops$502
St. John's
St. John'snonstop$347
Santo Domingo
Santo Domingononstop$243
Oranjestad
Oranjestad1 stop$581
Kingston
Kingston2 stops$617
Port of Spain
Port of Spain1 stop$511
Bridgetown
Bridgetown1 stop$425
Willemstad
Willemstadnonstop$381
Castries
Castries2 stops$502
St. John's
St. John'snonstop$347

Book Cheap Simpson Bay to Caribbean Islands Plane Tickets

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

So, Nov 16 - Mi, Nov 19
Arajet Logo
12:25 pm - 4:39 pmSXM-SJU
4h 14m1 stop
Arajet Logo
3:20 pm - 7:52 pmSJU-SXM
4h 32m1 stop
$215Arajet
Find Deal
So, Nov 30 - Mi, Dez 3
Arajet Logo
12:25 pm - 4:39 pmSXM-SJU
4h 14m1 stop
Arajet Logo
3:20 pm - 7:52 pmSJU-SXM
4h 32m1 stop
$223Arajet
Find Deal
Mo, Dez 8 - Mi, Dez 10
Winair Logo
9:00 am - 9:15 amSXM-SBH
0h 15mnonstop
Winair Logo
5:25 pm - 5:40 pmSBH-SXM
0h 15mnonstop
$288Winair
Find Deal
Do, Feb 12 - Di, Feb 17
Winair Logo
9:00 am - 9:15 amSXM-SBH
0h 15mnonstop
Winair Logo
5:25 pm - 5:40 pmSBH-SXM
0h 15mnonstop
$290Winair
Find Deal
Do, Jan 22 - Do, Jan 29
Sunrise Airways Logo
3:30 pm - 5:15 pmSXM-DOM
1h 45m1 stop
Sunrise Airways Logo
12:55 pm - 2:40 pmDOM-SXM
1h 45m1 stop
$394Sunrise Airways
Find Deal
Fr, Nov 7 - Mo, Nov 10
Sunrise Airways Logo
2:25 pm - 5:45 pmSXM-DOM
3h 20m2 stops
Sunrise Airways Logo
12:55 pm - 2:40 pmDOM-SXM
1h 45m1 stop
$423Sunrise Airways
Find Deal
Sa, Okt 18 - Sa, Okt 25
Caribbean Airlines Logo
6:10 pm - 12:00 pmSXM-KIN
18h 50m2 stops
Caribbean Airlines Logo
1:50 pm - 5:10 pmKIN-SXM
2h 20mnonstop
$617Caribbean Airlines
Find Deal
Sa, Jan 31 - Sa, Feb 7
Caribbean Airlines Logo
10:25 am - 11:55 amSXM-KIN
2h 30mnonstop
Caribbean Airlines Logo
1:50 pm - 5:10 pmKIN-SXM
2h 20mnonstop
$619Caribbean Airlines
Find Deal
Fr, Nov 21 - Mi, Nov 26
American Airlines Logo
3:20 pm - 10:13 pmSXM-KIN
7h 53m1 stop
American Airlines Logo
7:30 am - 4:22 pmKIN-SXM
7h 52m1 stop
$1,199American Airlines
Find Deal
Di, Sep 30 - Di, Okt 7
American Airlines Logo
2:20 pm - 11:25 amSXM-GCM
22h 05m2 stops
American Airlines Logo
12:25 pm - 1:37 pmGCM-SXM
24h 12m2 stops
$1,301American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Simpson Bay to Caribbean Islands flights

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

What is the cheapest Simpson Bay to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Simpson Bay found in the last 72 hours was to Santo Domingo, at $198 round-trip. The most popular route is from Simpson Bay (SXM) to Santo Domingo (SDQ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $198.

Can I save money by flying with a layover from Simpson Bay to Caribbean Islands?

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 $493, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Simpson Bay to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Simpson Bay to Caribbean Islands, 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 Simpson Bay to Caribbean Islands is June, when tickets cost $161 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $406 and $342 respectively.

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

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

For Simpson Bay to Caribbean Islands, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Caribbean Islands back to Simpson Bay, the best deals are generally found on Friday, with Thursday being the most expensive.

How far in advance should I book a flight from Simpson Bay to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Simpson Bay to Caribbean Islands, 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 Simpson Bay to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$156
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Simpson Bay to Santo Domingo

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

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $229 on average. Morning departures are around 45% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $333.

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 $266 one-way - $382 round-trip; Port of Spain $259 one-way - $706 round-trip; Santo Domingo $169 one-way - $271 round-trip

Reviews of the top airlines flying from Simpson Bay to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Caribbean Islands. 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 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.
8.1
Caribbean AirlinesOverall score based on 179 reviews
6.8Entertainment
6.9Food
8.1Boarding
8.4Crew
7.9Comfort
Airline reviews

just a child who screamed and threw tantrums the entire flight

8.0 ExcellentAnonymous, Sep 2025YYZ - POS
Read more Caribbean Airlines reviews

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

Flight ended up being longer than anticipated because we had to reroute to the Bahamas. So a hour and half flight turned into 5 hours. 0/10.

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

Checking in, boarding, the food and crew were all excellent. It was my first time traveling on Caribbean Airlines and trust me it’s the only airline I’ll be flying on as of now as long as it’s going my way😁. The service was unbelievably good I don’t regret missing my flight on flair at all cause I wouldn’t have realized how great the service is on Caribbean Airlines

The flight could'nt be better ,the comfort ,the crew and everything was good.i will definitely fly with this sirline again.

I love my entire experience. What I love most, was the friendliness and helpfulness of the staff at check-in and that of the crew on the flight. Their Customer Service was paramount.

The flight crew was extremely hospitable, though there was a lot of turbulence, they made it a good experience. The only negative was the inflight experience for economy class. There wasn’t any, or at least non that I was aware of.

I liked the friendliness of the employees at the airport

I liked the extra leg room in Caribbean plus. Worth the extra money. The food could have been more balanced, there was no salad or veggies

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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