$186 Find Cheap Flights from Santiago 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 Santiago to Caribbean Islands departing on 10/14. 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 Santiago 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 Santiago to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Santiago to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$360
Santo Domingo
Santo Domingo1 stop$428
Punta Cana
Punta Cananonstop$360
Santo Domingo
Santo Domingo1 stop$428

Book Cheap Santiago 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 Santiago 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 Santiago to Caribbean Islands

Wed, Nov 19 - Sun, Nov 30
Arajet Logo
6:00 am - 1:19 pmSCL-PUJ
8h 19mnonstop
Arajet Logo
8:07 pm - 4:55 amPUJ-SCL
7h 48mnonstop
$360Arajet
Find Deal
Tue, Oct 14 - Tue, Oct 21
Multiple Airlines Logo
7:10 am - 4:50 pmSCL-SJU
10h 40m1 stop
Multiple Airlines Logo
9:55 am - 3:35 amSJU-SCL
16h 40m1 stop
$384Multiple Airlines
Find Deal
Fri, Nov 21 - Tue, Dec 2
Copa Airlines Logo
3:23 am - 12:17 pmSCL-CUR
9h 54m1 stop
Copa Airlines Logo
1:16 pm - 3:43 amCUR-SCL
13h 27m1 stop
$389Copa Airlines
Find Deal
Wed, Oct 29 - Thu, Nov 6
Avianca Logo
1:35 am - 11:35 amSCL-SJU
11h 00m1 stop
Avianca Logo
6:30 pm - 5:30 amSJU-SCL
10h 00m1 stop
$403Avianca
Find Deal
Thu, Oct 30 - Wed, Nov 12
Copa Airlines Logo
3:35 am - 1:04 pmSCL-SJU
10h 29m1 stop
Copa Airlines Logo
5:27 am - 11:41 pmSJU-SCL
17h 14m1 stop
$406Copa Airlines
Find Deal
Tue, Oct 28 - Wed, Nov 5
Sky Airline Logo
1:35 am - 4:25 pmSCL-PUJ
15h 50m2 stops
Sky Airline Logo
5:45 pm - 5:50 amPUJ-SCL
11h 05m1 stop
$434Sky Airline
Find Deal
Thu, Sep 25 - Tue, Sep 30
Sky Airline Logo
1:35 am - 4:35 pmSCL-PUJ
16h 00m2 stops
Sky Airline Logo
5:40 pm - 6:00 amPUJ-SCL
11h 20m1 stop
$435Sky Airline
Find Deal
Thu, Nov 13 - Wed, Nov 19
Avianca Logo
1:35 am - 11:00 amSCL-AUA
10h 25m1 stop
Avianca Logo
12:05 pm - 5:30 amAUA-SCL
16h 25m1 stop
$448Avianca
Find Deal
Sat, Mar 7 - Sun, Mar 22
LATAM Airlines Logo
4:35 am - 5:40 pmSCL-CUR
14h 05m1 stop
LATAM Airlines Logo
6:50 pm - 11:06 amCUR-SCL
15h 16m2 stops
$453LATAM Airlines
Find Deal
Mon, Mar 9 - Tue, Mar 24
LATAM Airlines Logo
8:59 pm - 5:40 pmSCL-CUR
21h 41m2 stops
LATAM Airlines Logo
6:50 pm - 2:05 pmCUR-SCL
18h 15m1 stop
$461LATAM Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Santiago to Caribbean Islands flights

Get data-powered insights and trends into flights from Santiago to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Santiago 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 Santiago found in the last 72 hours was to Punta Cana, at $335 round-trip. The most popular route is from Santiago (SCL) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $335.

Can I save money by flying with a layover from Santiago 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 $481, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Santiago to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Santiago 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 Santiago to Caribbean Islands is October, when tickets cost $432 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $620 and $600 respectively.

What’s the cheapest day of the week to fly from Santiago to Caribbean Islands?

The average price of all round-trip flights from Santiago to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Santiago to Caribbean Islands. For your return ticket, we recommend flying on a Sunday and avoiding Saturdays for the best deals.

How far in advance should I book a flight from Santiago 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 Santiago 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 Santiago to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonAugust
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 8% lower on average.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Santiago 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 Santiago to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Santiago 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 Santiago 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 Santiago 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 Santiago 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 Santiago 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 at night, when round-trip flights cost $546 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 $609.

Reviews of the top 5 airlines serving from Santiago to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Santiago 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 Santiago 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.
7.6
Copa AirlinesOverall score based on 1531 reviews
7.4Comfort
7.8Boarding
6.8Food
8.1Crew
6.8Entertainment
Airline reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

10.0 ExcellentNeil, Aug 2025PTY - BGI
Read more Copa Airlines reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Did upgrade, travel in business it was great (more room I could sleep)

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

My biggest complaint is the comfort. I am not tall and there was no legroom. It was very uncomfortable. During my transfer in Sao Paola, the flight was slightly delayed so boarding was confusing because there were no instructions in English.

Bought a ticket that included a bag and they still charged me to check it in, latam is the worst airline.

Because the flight was late, we lost the connection to Brazil. You, Delta delayed, and you Delta anticipated the door closing in 15 min from Miami to GRU. Why? It caused a lot of stress! I almost could not see my mother in law alive because of your delay.

Lost ,y connection due to a mechanical delay, huge line to get new connection and vouchers

It’s a delta flight operated by LATAM. The whole ticket sale is a mess, delta changed my flight but didn’t update it in LATAM system, I couldn’t get my boarding pass, it took me hours to resolve this issue with delta. I had to change my travel plan. No apology from Delta even though it’s their fault.

The boarding and new bag drop-off process was confusing and causing massive delays.

I travel often with LATAM, it never disappoints me. The service is great, nice crew, latest and some classic movies. I got 3 small meals, cannot complaint. I’ll definitely travel again with them.

We didn’t have any entertainment. I tried to go online without success. The airplane was extremely cold and they didn’t have blankets.

It was good, however the airplane was really cold. We received snacks and the crew was friendly.

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

Usb plugs for charging your phone does not work in every flight. uncomfortable chairs even in higher categories.

The usb plugs for charging your phone didn’t work, the seats were coarse and hard. Not very comfortable. No inflight WiFi

The seats were uncomfortable and barely reclined at all. Very little leg room despite being business class. The crew was friendly and the food was good. Had to use my own phone for in-flight entertainment.

Avianca is not what it used to be. So disappointing

The incoming plane was late and no information was shared. They even announced we would board in 10 muntes 40 minutes prior to the plane arriving, and the website said until takeoff that we had taken off an hour earlier

Boarding was excessively slow. They do it by groups in a way that it doesn’t make sense. After business class , ppl that need assistance and any other priority group they should have ppl board from the back to the front. First rows 20+. Then 15+. Then 10, etc. having ppl sitting in the back board last makes no sense. The libe backame long as soon as ppl on rows 10 or so where told to board. The line went all the way up the ramp and tunnel for 25 mins.

Terrible, We had to stay in Bogota for two days due to weather but the airline did not provide for the same day flight. Only two days later

Purchased a business class ticket and got a economy seat with center seat blocked they call it business. 3100usd ticket on a flight where economy costs 500usd The biggest scam insult have had on a regular airline. Avianca should be in the low cost category and kicked out of Star Alliance. I want the difference to be credited. Ets see what Avianca does. No reply so far. Avianca = low cost airline. Beware

Business class seats did not lie flat. There was only powdered milk for your coffee....in Business Class!! Food was good.

Excellent flight and one of the smoothest landing I’ve ever experienced

This airline scams people into paying multiple times for their baggage. I prepaid $150 for my son's baggage roundtrip from Miami to Cusco. We he checked in at Miami, they said it was not paid for in their system and they would not let him board the plane unless he paid $88 for the baggage despite him showing the receipt that I had already paid. THEN, when he landed in Lima, they told him he had to pay another $73 for his bag to get to Cusco or they would not let him board...even though he now had 2 receipts showing he paid! I called to let them know of this error and that I wanted to be refunded for the additional $161 they charged him. I also wanted to make sure that it was showing in the system that we had already paid for the baggage so that this would not happen again on his return flight. They assured me it was in the system, but when we went to check in for his return flight, they said it was not in the system (despite me showing all 3 of our previous receipts and where it had come out of my bank account) and made us pay another $73 for his baggage or they would not let him on his return flight! I have called twice and emailed twice with no resolution. We paid $384 for one normal size and weight bag. They did the same thing to my mom on a flight the week before! I truly believe that they are scamming customers out of hundreds of dollars. I would like to know what agency I can report this fraud to as trying to address it with the airline has not worked.

Disorganized. Multiple flight time changes both ways and double dipping charging for carry on bags/checked bags. We booked directly through Sky to avoid 3rd party agent hassle. Unlikely to fly again with this airline.

Changed schedule without notice , canceled flight, mediocre competition, no help with the lost connecting flights.

Bare bones flight no entertainment minimal, if any food or beverage. warm beer only if you want a cocktail

Sky canceled our 8 am flight at 1 am. However Kiwi.com, who we used to book our flight (because sky airways online system would always give us an error message when we entered our payment information ) didn’t claim it was a cancellation but simply a 12.5 hour delay, and rescheduled our flight for 8:30 pm. This would have left us stuckk at the airport for 12.5 more hours, as we we staying at the Wyndham hotel at the airport. We were unable to request a refund this through kiwi because they don’t allow refunds for any schedule changes with less than 24 hours difference. Kayak and sky airline’s own websites showed the flight as cancelled. Only kiwi showed it as a very very very delayed flight. This way kiwi can keep our money. Ugh. We tried for hours to request a refund at the sky airlines website, but there was always an error at the very last step where you enter your refund credit card information. We ended up being forced to request refund vouchers which are good for 12 months but which we will likely never use. We ended up booking new flights with Latam airlines that got us out at 8:40 am. We will never use kiwi.com again.

my flight was canceled without reason or possibility of resuming another flight within the time frame of my trip I could not contact an adviser either by email or by telephone because no communication possible on the website I could not have the flight reimbursed I find this way of doing things by the company inadmissible I have lost €250 it is theft I do not recommend this company and I consider that you have not done your job because I have not obtained any help from your part

J’ai réservé avec Kayak. Sur mon billet de confirmation il était noté que j’avais droit à des bagages pour chaque passager mais on m’a fait payer 36 dolllars pour l’un des passagers.

Flight check in Lima to Cusco all went very smoothly and plane boarded on time. All in all a great experience for a low cost fare.

Don’t ever book with them. They are worse than Ryanair and you will end up paying more for the worse possible airline and deal with ignorant people who don’t know what “customer” is. Avoid at all costs

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