$129 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 2/1. 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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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$257
Oranjestad
Oranjestad1 stop$598
Kingston
Kingston1 stop$495
Port of Spain
Port of Spainnonstop$418
Bridgetown
Bridgetown1 stop$401
Willemstad
Willemstadnonstop$402
Castries
Castriesnonstop$551
St. John's
St. John's1 stop$344
Santo Domingo
Santo Domingononstop$257
Oranjestad
Oranjestad1 stop$598
Kingston
Kingston1 stop$495
Port of Spain
Port of Spainnonstop$418
Bridgetown
Bridgetown1 stop$401
Willemstad
Willemstadnonstop$402
Castries
Castriesnonstop$551
St. John's
St. John's1 stop$344

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

Thu, Nov 13 - Thu, Nov 20
Arajet Logo
11:30 am - 1:00 pmSXM-SDQ
1h 30mnonstop
Arajet Logo
8:58 am - 10:25 amSDQ-SXM
1h 27mnonstop
$257Arajet
Find Deal
Mon, Dec 22 - Thu, Jan 8
Copa Airlines Logo
12:24 pm - 2:26 amSXM-SDQ
14h 02m1 stop
Copa Airlines Logo
7:05 pm - 11:24 amSDQ-SXM
16h 19m1 stop
$260Copa Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Arajet Logo
11:30 am - 1:00 pmSXM-SDQ
1h 30mnonstop
Arajet Logo
8:58 am - 10:25 amSDQ-SXM
1h 27mnonstop
$261Arajet
Find Deal
Wed, Jan 14 - Wed, Jan 21
Arajet Logo
9:35 am - 11:05 amSXM-SDQ
1h 30mnonstop
Arajet Logo
7:03 am - 8:30 amSDQ-SXM
1h 27mnonstop
$263Arajet
Find Deal
Sun, Nov 16 - Wed, Nov 19
Winair Logo
10:10 am - 10:25 amSXM-SBH
0h 15mnonstop
Winair Logo
4:25 pm - 4:40 pmSBH-SXM
0h 15mnonstop
$288Winair
Find Deal
Wed, Dec 10 - Sun, Dec 14
Winair Logo
9:00 am - 9:15 amSXM-SBH
0h 15mnonstop
Winair Logo
4:55 pm - 5:10 pmSBH-SXM
0h 15mnonstop
$293Winair
Find Deal
Fri, Feb 13 - Wed, Feb 18
Sunrise Airways Logo
2:25 pm - 5:45 pmSXM-DOM
3h 20m2 stops
Sunrise Airways Logo
8:30 am - 10:15 amDOM-SXM
1h 45m1 stop
$471Sunrise Airways
Find Deal
Fri, Mar 6 - Mon, Mar 9
Caribbean Airlines Logo
11:35 am - 1:45 pmSXM-SJU
26h 10m3 stops
Caribbean Airlines Logo
4:00 pm - 10:45 amSJU-SXM
18h 45m3 stops
$545Caribbean Airlines
Find Deal
Tue, Mar 10 - Fri, Mar 13
Caribbean Airlines Logo
6:45 pm - 1:45 pmSXM-SJU
19h 00m2 stops
Caribbean Airlines Logo
3:15 pm - 9:25 amSJU-SXM
18h 10m3 stops
$577Caribbean Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Anguilla Air Services Logo
5:00 pm - 8:45 amSXM-SBH
15h 45m1 stop
Anguilla Air Services Logo
9:30 am - 12:40 pmSBH-SXM
3h 10m1 stop
$964Anguilla Air Services
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 $232 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 $339.

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 $497, 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 $160 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $541 and $336 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 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$129
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 8% increase 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 $230 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 $217 one-way - $394 round-trip; Port of Spain $285 one-way - $853 round-trip; Gustavia $208 one-way - $303 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.
8.0
Caribbean AirlinesOverall score based on 193 reviews
7.8Comfort
6.8Food
6.7Entertainment
8.4Crew
8.1Boarding
Airline reviews

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.

10.0 ExcellentAnonymous, Oct 2025POS - MCO
Read more Caribbean Airlines reviews

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.

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.

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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