$60 Find Cheap Flights from Simpson Bay to Caribbean Islands - 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 Simpson Bay to Caribbean Islands departing on 8/5. 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.
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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$336
Oranjestad
Oranjestad1 stop$461
Kingston
Kingstonnonstop$662
Port of Spain
Port of Spain1 stop$469
Bridgetown
Bridgetown1 stop$407
Willemstad
Willemstadnonstop$389
Castries
Castries1 stop$648
St. John's
St. John's1 stop$373
Santo Domingo
Santo Domingononstop$336
Oranjestad
Oranjestad1 stop$461
Kingston
Kingstonnonstop$662
Port of Spain
Port of Spain1 stop$469
Bridgetown
Bridgetown1 stop$407
Willemstad
Willemstadnonstop$389
Castries
Castries1 stop$648
St. John's
St. John's1 stop$373

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

Wed, Aug 19 - Wed, Aug 26
Winair Logo
9:00 am - 9:15 am
SXM
-
SBH
0h 15mnonstop
Winair Logo
4:20 pm - 4:35 pm
SBH
-
SXM
0h 15mnonstop
$205Winair
Wed, Aug 12 - Wed, Aug 19
Winair Logo
11:10 am - 11:25 am
SXM
-
SBH
0h 15mnonstop
Winair Logo
5:30 pm - 5:45 pm
SBH
-
SXM
0h 15mnonstop
$206Winair
Wed, Oct 14 - Tue, Oct 20
Multiple Airlines Logo
9:35 am - 1:50 pm
SXM
-
SJU
4h 15m
1 stop
Multiple Airlines Logo
3:50 pm - 5:00 pm
SJU
-
SXM
1h 10mnonstop
$259Multiple Airlines
Wed, Oct 14 - Tue, Oct 20
Multiple Airlines Logo
9:35 am - 1:50 pm
SXM
-
SJU
4h 15m
1 stop
Multiple Airlines Logo
11:40 am - 12:50 pm
SJU
-
SXM
1h 10mnonstop
$282Multiple Airlines
Sun, Aug 30 - Sun, Sep 13
Arajet Logo
11:30 am - 1:00 pm
SXM
-
SDQ
1h 30mnonstop
Arajet Logo
8:58 am - 10:25 am
SDQ
-
SXM
1h 27mnonstop
$336Arajet
Wed, Sep 2 - Wed, Sep 9
Arajet Logo
9:35 am - 11:05 am
SXM
-
SDQ
1h 30mnonstop
Arajet Logo
7:03 am - 8:30 am
SDQ
-
SXM
1h 27mnonstop
$346Arajet
Fri, Aug 28 - Tue, Sep 1
Sunrise Airways Logo
1:00 pm - 8:45 am
SXM
-
DOM
19h 45m
2 stops
Sunrise Airways Logo
9:15 am - 12:15 pm
DOM
-
SXM
3h 00m
1 stop
$436Sunrise Airways
Tue, Oct 20 - Sat, Oct 31
Sunrise Airways Logo
1:00 pm - 5:15 pm
SXM
-
DOM
4h 15m
1 stop
Sunrise Airways Logo
9:15 am - 12:15 pm
DOM
-
SXM
3h 00m
1 stop
$445Sunrise Airways
Sat, Oct 24 - Sat, Oct 31
Caribbean Airlines Logo
10:25 am - 11:55 am
SXM
-
KIN
2h 30mnonstop
Caribbean Airlines Logo
1:50 pm - 5:10 pm
KIN
-
SXM
2h 20mnonstop
$676Caribbean Airlines
Sat, Oct 24 - Sat, Oct 31
Caribbean Airlines Logo
6:10 pm - 12:00 pm
SXM
-
KIN
18h 50m
2 stops
Caribbean Airlines Logo
1:50 pm - 5:10 pm
KIN
-
SXM
2h 20mnonstop
$684Caribbean 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 5 days was to Santo Domingo, at $326 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 5 days was $326.

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

The average price for all round-trip flights from Simpson Bay to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $226 on average. Morning departures are around 49% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $352.

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 $574, 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 $356 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $411 and $406 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, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Caribbean Islands back to Simpson Bay, the best deals are generally found on Monday, with Thursday being the most expensive.

Good to know

Low season

January

Cheapest flight

$60
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Simpson Bay to Gustavia

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.

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: Road Town $220 one-way - $507 round-trip; Gustavia $135 one-way - $206 round-trip; Santo Domingo $316 one-way - $376 round-trip

Reviews of the top 4 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.
8.5
WinairOverall score based on 4 reviews
8.5Boarding
8.0Comfort
7.5Entertainment
7.5Food
9.5Crew
Airline reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

6.0 GoodAnonymous, May 2026
SBH - SXM
Read more Winair reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

Boarding the flight was smooth and the flight was not full so i had an extra seat essentially

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

Excellent experience this was my first time booking with Kayak.

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

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

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

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

We booked Caribbean Plus and Business Class.. The problem was that in Toronto the staff we would collect our bags in POS, but we had to pick up our luggage in GEO, do immigration, and customers, and go from one terminal to the other with all our suitcases and 2 kids.. Not nice and not cool. Wont do that layover in GEO again

Flight was good, staff and crew was informative. Should have some sort and of entertainment during the flight given the price to fly.🙏

Wearing masks should be enforced in the lounge. There were a few patrons who just weren't wearing them even though it's mandatory in public places in Trinidad and Tobago. Other than that, it was a great experience.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

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

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