$120 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 8/8. 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, 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 Simpson Bay to Caribbean Islands, as well as popular online travel agencies
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Best Caribbean Islands Flight Deals from Simpson Bay

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingononstop$249
Oranjestad
Oranjestad1 stop$371
Kingston
Kingstonnonstop$514
Port of Spain
Port of Spain1 stop$447
Bridgetown
Bridgetownnonstop$414
Willemstad
Willemstadnonstop$382
Castries
Castries1 stop$532
St. John's
St. John'snonstop$348
Santo Domingo
Santo Domingononstop$249
Oranjestad
Oranjestad1 stop$371
Kingston
Kingstonnonstop$514
Port of Spain
Port of Spain1 stop$447
Bridgetown
Bridgetownnonstop$414
Willemstad
Willemstadnonstop$382
Castries
Castries1 stop$532
St. John's
St. John'snonstop$348

Cheap Flights from Simpson Bay to Caribbean Islands

 
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

Fri, Aug 1 - Mon, Aug 4
Frontier Logo
6:26 pm - 7:29 pmSXM-SJU
1h 03mnonstop
Frontier Logo
4:18 pm - 5:21 pmSJU-SXM
1h 03mnonstop
$144Frontier
Find Deal
Wed, Sep 10 - Sun, Sep 14
Arajet Logo
9:17 am - 10:47 amSXM-SDQ
1h 30mnonstop
Arajet Logo
6:03 pm - 7:30 pmSDQ-SXM
1h 27mnonstop
$249Arajet
Find Deal
Mon, Jul 14 - Mon, Jul 21
Winair Logo
10:00 am - 10:15 amSXM-SBH
0h 15mnonstop
Winair Logo
4:30 pm - 4:45 pmSBH-SXM
0h 15mnonstop
$282Winair
Find Deal
Thu, Oct 9 - Sun, Oct 12
Winair Logo
9:00 am - 9:15 amSXM-SBH
0h 15mnonstop
Winair Logo
5:25 pm - 5:40 pmSBH-SXM
0h 15mnonstop
$283Winair
Find Deal
Sat, Aug 9 - Wed, Aug 13
 Logo
6:26 pm - 7:29 pmSXM-SJU
1h 03mnonstop
 Logo
3:20 pm - 4:30 pmSJU-SXM
25h 10m1 stop
Fri, Jul 18 - Sun, Jul 20
 Logo
3:30 pm - 7:00 pmSXM-DOM
3h 30m1 stop
 Logo
8:30 am - 10:15 amDOM-SXM
1h 45m1 stop
Mon, Sep 1 - Fri, Sep 5
Caribbean Airlines Logo
11:35 am - 2:00 pmSXM-SJU
26h 25m1 stop
Caribbean Airlines Logo
3:30 pm - 9:25 amSJU-SXM
17h 55m1 stop
$535Caribbean Airlines
Find Deal
Tue, Sep 16 - Sat, Oct 4
Caribbean Airlines Logo
11:40 am - 1:10 pmSXM-KIN
2h 30mnonstop
Caribbean Airlines Logo
1:50 pm - 5:10 pmKIN-SXM
2h 20mnonstop
$607Caribbean Airlines
Find Deal
Mon, Sep 1 - Mon, Sep 8
American Airlines Logo
2:45 pm - 11:00 amSXM-KIN
21h 15m1 stop
American Airlines Logo
6:00 am - 1:19 pmKIN-SXM
30h 19m1 stop
$1,027American Airlines
Find Deal
Sun, Dec 14 - Wed, Dec 31
American Airlines Logo
3:15 pm - 12:15 pmSXM-KIN
22h 00m1 stop
American Airlines Logo
8:25 am - 4:15 pmKIN-SXM
6h 50m1 stop
$1,178American Airlines
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Simpson Bay to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Simpson Bay found in the last 72 hours was to Santo Domingo, at $154 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 $154.

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 $655, 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 July, when tickets cost $159 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $342 and $272 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, Wednesday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Simpson Bay, the best deals are generally found on Monday, with Wednesday 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
High seasonJuly
Cheapest flight$120
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 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 $233 on average. Morning departures are around 43% 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: Port of Spain $301 one-way - $882 round-trip; Gustavia $175 one-way - $284 round-trip; Santo Domingo $194 one-way - $190 round-trip

Reviews of the top 3 airlines serving 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.
8.2
Caribbean AirlinesOverall score based on 163 reviews
8.2Boarding
6.9Food
8.5Crew
7.9Comfort
6.8Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Jun 2025YYZ - KIN
Read more Caribbean Airlines reviews

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

The Flight itself was smooth and uneventful. The crew was polite and caring. I used the Lounge in Piarco and the service was STELLAR

Crew were quite friendly. Food was very poor considering the price of the ticket and the flight time. Could not charge my phone due to USB charger not working..

The food wasn’t good. Need better food. There wasn’t any entertainment.

STEWARDESSES WERE AWESOME! The food could be a bit better. Rice was SOGGY with gravy and the chicken was RUBBERY.

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

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

Seats were roomy. Lavatories were surprisingly big and clean. Plenty of entertainment available. We were fed and offered drinks, multiple times during the flight.

British Airways staff are very polite and willing to help.

Any sort of gluten free snack option would be nice

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

The flight was late and we missed this connecting flight. American Airlines refused to put us anywhere for the night for their snafu. We had to find our own accommodations in Miami, and it was expensive for a crappy hotel.

My seat was horrible. I think it was broken in several places. Other than that, the crew was great and the plane was clean

2/29/2025: Tulum to DFW. Delay as usual with no explanation from AA. Three friends and I had a connecting flight from DFW to STL. We would have missed the latter without the delayed connecting flight, dashing through customs, and running through the airport. Did I mention our trip to Tulum on American was rerouted to Cancun and shuttle from Cancun to Tulum, arriving at our resort destination at midnight vs the 4 PM scheduled arrival? AA provided a lunch voucher for $12.00. The least expensive menu item was $9.99 for green beans. I will avoid traveling with AA as much as possible.

At least it was a short flight. Greyhound with wings.

Everything you need to know for your flight to Caribbean Islands

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