$104 Find Cheap Flights from Caribbean Islands to Simpson Bay - 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 to Simpson Bay departing on 10/10. 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 Caribbean Islands to Simpson Bay

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

Tue, Sep 8 - Sun, Sep 13
Winair Logo
4:10 pm - 4:25 pm
SBH
-
SXM
0h 15mnonstop
Winair Logo
11:15 am - 11:30 am
SXM
-
SBH
0h 15mnonstop
$205Winair
Sun, Sep 6 - Sun, Sep 13
Sunrise Airways Logo
11:45 am - 12:15 pm
SKB
-
SXM
0h 30mnonstop
Sunrise Airways Logo
1:00 pm - 1:30 pm
SXM
-
SKB
0h 30mnonstop
$327Sunrise Airways
Thu, Aug 20 - Sat, Aug 22
Sunrise Airways Logo
11:45 am - 12:15 pm
SKB
-
SXM
0h 30mnonstop
Sunrise Airways Logo
1:00 pm - 1:30 pm
SXM
-
SKB
0h 30mnonstop
$328Sunrise Airways
Fri, Aug 28 - Mon, Aug 31
Sunrise Airways Logo
11:45 am - 12:15 pm
SKB
-
SXM
0h 30mnonstop
Sunrise Airways Logo
1:00 pm - 1:30 pm
SXM
-
SKB
0h 30mnonstop
$329Sunrise Airways
Thu, Sep 17 - Thu, Sep 24
Arajet Logo
8:58 am - 10:25 am
SDQ
-
SXM
1h 27mnonstop
Arajet Logo
11:30 am - 1:00 pm
SXM
-
SDQ
1h 30mnonstop
$350Arajet
Thu, Dec 31 - Thu, Jan 7
Arajet Logo
8:58 am - 10:25 am
SDQ
-
SXM
1h 27mnonstop
Arajet Logo
11:30 am - 1:00 pm
SXM
-
SDQ
1h 30mnonstop
$352Arajet
Sat, Oct 10 - Sun, Nov 1
interCaribbean Airways Logo
1:45 pm - 2:25 pm
EIS
-
SXM
0h 40mnonstop
interCaribbean Airways Logo
1:25 pm - 2:05 pm
SXM
-
EIS
0h 40mnonstop
$355interCaribbean Airways
Tue, Aug 4 - Fri, Aug 7
Winair Logo
7:15 am - 1:35 pm
EIS
-
SXM
6h 20m
1 stop
Winair Logo
4:30 pm - 7:00 pm
SXM
-
EIS
2h 30m
1 stop
$378Winair
Sat, Sep 19 - Sat, Sep 26
Caribbean Airlines Logo
1:50 pm - 5:10 pm
KIN
-
SXM
2h 20mnonstop
Caribbean Airlines Logo
10:25 am - 11:55 am
SXM
-
KIN
2h 30mnonstop
$659Caribbean Airlines
Sat, Sep 19 - Sat, Sep 26
Caribbean Airlines Logo
1:50 pm - 5:10 pm
KIN
-
SXM
2h 20mnonstop
Caribbean Airlines Logo
6:10 pm - 12:00 pm
SXM
-
KIN
18h 50m
2 stops
$669Caribbean Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$104
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Road Town to Simpson Bay

FAQs for booking flights from Caribbean Islands to Simpson Bay

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

    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 Caribbean Islands to Simpson Bay.

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

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

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

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

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

Reviews of the top 5 airlines serving from Caribbean Islands to Simpson Bay

 
Need help choosing which airline to fly with from Caribbean Islands to Simpson Bay? 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
7.5Entertainment
9.5Crew
7.5Food
8.0Comfort
8.5Boarding
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.

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.

Excellent experience this was my first time booking with Kayak.

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

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

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

Checking in was seamless Flight left on time Flight arrived 45 minutes ahead of time, Overall, it was a good experience

When I booked my flight I choose a seat which was the window in the middle of the aircraft. My seating was change without notice and I was in the middle seat which cause me anxiety. Hated this whole flight experience

From the point of checking in I felt as if the agents and crew were like family and friends. The best customer service experience I ever had.

To be honest I did not like anything there because the flight was delay and poor customer service!

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.

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

Flew St Vincent to Barbados on an ATR-40 (?), seating about 60 passengers. Pretty tight in there. Flt. attendant was very friendly. Short flight - up & down in 40 minutes.

No food, no entertainment - half-hour flight (up & down) Smallest plane I’ve ever been on - maybe 60 passenger capacity?

I've had bad flights with InterCaribbean before (cancellations, no gate agents, etc.), but this one went perfectly smoothly!

Long delay. No AC on the flight from Barbados to St. Lucia.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Everything you need to know for your flight to Simpson Bay

Information on the airport you'll fly into in Simpson Bay