$126 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 3/1. 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 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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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$233
Oranjestad
Oranjestad1 stop$535
Kingston
Kingston1 stop$572
Port of Spain
Port of Spainnonstop$685
Bridgetown
Bridgetownnonstop$431
Willemstad
Willemstadnonstop$403
St. John's
St. John'snonstop$345
Santo Domingo
Santo Domingononstop$233
Oranjestad
Oranjestad1 stop$535
Kingston
Kingston1 stop$572
Port of Spain
Port of Spainnonstop$685
Bridgetown
Bridgetownnonstop$431
Willemstad
Willemstadnonstop$403
St. John's
St. John'snonstop$345

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

Mon, Feb 2 - Fri, Feb 6
FlexFlight Logo
11:30 am - 11:45 am
SXM
-
SBH
0h 15mnonstop
FlexFlight Logo
4:00 pm - 4:15 pm
SBH
-
SXM
0h 15mnonstop
$184FlexFlight
Fri, Jan 16 - Fri, Jan 16
FlexFlight Logo
10:00 am - 10:15 am
SXM
-
SBH
0h 15mnonstop
FlexFlight Logo
4:00 pm - 4:15 pm
SBH
-
SXM
0h 15mnonstop
$188FlexFlight
Sun, Feb 1 - Sun, Feb 8
Arajet Logo
11:30 am - 1:00 pm
SXM
-
SDQ
1h 30mnonstop
Arajet Logo
8:58 am - 10:25 am
SDQ
-
SXM
1h 27mnonstop
$233Arajet
Thu, Jan 29 - Sat, Jan 31
Multiple Airlines Logo
11:30 am - 11:45 am
SXM
-
SBH
0h 15mnonstop
Multiple Airlines Logo
5:30 pm - 5:45 pm
SBH
-
SXM
0h 15mnonstop
$239Multiple Airlines
Wed, Jan 14 - Wed, Jan 21
Multiple Airlines Logo
9:35 am - 11:05 am
SXM
-
SDQ
1h 30mnonstop
Multiple Airlines Logo
7:03 am - 8:30 am
SDQ
-
SXM
1h 27mnonstop
$240Multiple Airlines
Thu, Mar 19 - Thu, Mar 26
Arajet Logo
11:30 am - 1:00 pm
SXM
-
SDQ
1h 30mnonstop
Arajet Logo
8:58 am - 10:25 am
SDQ
-
SXM
1h 27mnonstop
$243Arajet
Sat, Jan 31 - Mon, Feb 16
Winair Logo
11:10 am - 11:25 am
SXM
-
SBH
0h 15mnonstop
Winair Logo
4:15 pm - 4:30 pm
SBH
-
SXM
0h 15mnonstop
$310Winair
Fri, Jan 30 - Sun, Feb 15
Winair Logo
11:10 am - 11:25 am
SXM
-
SBH
0h 15mnonstop
Winair Logo
4:15 pm - 4:30 pm
SBH
-
SXM
0h 15mnonstop
$345Winair
Tue, Feb 3 - Tue, Feb 10
Caribbean Airlines Logo
11:40 am - 1:10 pm
SXM
-
KIN
2h 30mnonstop
Caribbean Airlines Logo
2:30 pm - 5:50 pm
KIN
-
SXM
2h 20mnonstop
$629Caribbean Airlines
Tue, Jan 27 - Tue, Feb 3
Caribbean Airlines Logo
11:40 am - 1:10 pm
SXM
-
KIN
2h 30mnonstop
Caribbean Airlines Logo
2:30 pm - 5:50 pm
KIN
-
SXM
2h 20mnonstop
$634Caribbean Airlines
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 $187 round-trip. The most popular route is from Simpson Bay (SXM) to Willemstad (CUR), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $402.

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 $495, 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 March, when tickets cost $151 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $552 and $322 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 Tuesday 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 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$126
Best time to beat the crowds with an average 15% drop 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 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 $227 on average. Morning departures are around 47% 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 $300 one-way - $545 round-trip; Gustavia $182 one-way - $205 round-trip; Santo Domingo $188 one-way - $198 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.
7.9
Caribbean AirlinesOverall score based on 211 reviews
8.3Crew
6.6Entertainment
7.8Comfort
6.7Food
8.0Boarding
Airline reviews

There was no flight. They canceled the flight with no knowledge to me, and I still haven’t received a refund

2.0 Mediocrejahbless, Dec 2025
FLL - KIN
Read more Caribbean Airlines reviews

There was no flight. They canceled the flight with no knowledge to me, and I still haven’t received a refund

Overall, it was good. There was no food or entertainment, which is why I put poor (it wasn't an issue though).

Nothing, they could have made some accommodation for an awful experience. Me and my family were not informed properly we we separated. They took me off the original flight i booked. I booked our flight at one price and called me and told me they were not honoring my rate and they charged me double of what I paid. Me and my family don’t want to ever use your services again.

This flight was great. The plane took off and arrived at the destination an hour early. The crew was pleasant. The food and entertainment options are minimal but adequate for a 1-hour flight. They passed out water and quickly supplied me with a fresh magazine since the previous one had the crossword section filled out.

Better movie and tv selections. Also, the overnight flight to Trinidad from Toronto, the staff were not very attentive. I did not see them for at least half the fight. They were behind their curtain a lot of the time, and they did not check on us before landing to make sure all landing requirements were met.

Little space for luggage and the flight was delayed by an hour.

The flight was delayed over a hour and that was over 15 hours in advance not good

At check in I had to pay for my seat that I already paid for on purchasing my ticket. The flight was over an hour late and the plane smelt gross.

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

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

The ticket you issued was an hour after when the real flight was

I didn’t get a chance to experience anything because the 3rd party company that receives payment did a really bad job. After I received confirmation number I went to bed then I tried to check in my confirmation number did not work then I received a massage that my payment did not go through I called the company to rectify the problem and I was told that confirmation the whole thing was cancelled and that they couldn’t do anything about it and hang up the phone. So I decided to purchase a new ticket from another airline. I will never use kayak again and I’ll make sure all the people in my circle doesn’t deal with you guys.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports