$137 Find Cheap Flights from Caribbean Islands to Santiago de los Caballeros

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Santiago de los Caballeros departing on 5/15. 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

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Cheap Flights from Caribbean Islands to Santiago de los Caballeros

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Santiago de los Caballeros 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 Santiago de los Caballeros

Thu, Apr 16 - Mon, Apr 20
JetBlue Logo
1:57 pm - 3:12 pm
SJU
-
STI
1h 15mnonstop
JetBlue Logo
4:22 pm - 5:33 pm
STI
-
SJU
1h 11mnonstop
$287JetBlue
Fri, May 29 - Wed, Jun 3
JetBlue Logo
5:23 pm - 6:33 pm
SJU
-
STI
1h 10mnonstop
JetBlue Logo
7:48 pm - 8:55 pm
STI
-
SJU
1h 07mnonstop
$288JetBlue
Fri, Apr 3 - Sun, Apr 12
Spirit Airlines Logo
12:55 pm - 1:49 am
SJU
-
STI
12h 54m
1 stop
Spirit Airlines Logo
2:46 am - 11:49 am
STI
-
SJU
9h 03m
1 stop
$297Spirit Airlines
Fri, Apr 3 - Mon, Apr 13
JetBlue Logo
4:08 pm - 5:21 pm
SJU
-
STI
1h 13mnonstop
JetBlue Logo
6:31 pm - 7:38 pm
STI
-
SJU
1h 07mnonstop
$303JetBlue
Fri, Apr 10 - Sat, Apr 11
Multiple Airlines Logo
4:08 pm - 5:21 pm
SJU
-
STI
1h 13mnonstop
Multiple Airlines Logo
2:46 am - 6:55 pm
STI
-
SJU
16h 09m
1 stop
$308Multiple Airlines
Thu, Apr 9 - Fri, Apr 17
JetBlue Logo
7:00 pm - 7:20 am
SJU
-
STI
12h 20m
1 stop
JetBlue Logo
4:22 pm - 5:33 pm
STI
-
SJU
1h 11mnonstop
$313JetBlue
Fri, Apr 17 - Mon, Apr 20
JetBlue Logo
1:57 pm - 3:12 pm
SJU
-
STI
1h 15mnonstop
JetBlue Logo
4:22 pm - 5:33 pm
STI
-
SJU
1h 11mnonstop
$315JetBlue
Wed, Apr 15 - Sun, Apr 19
JetBlue Logo
1:57 pm - 3:12 pm
SJU
-
STI
1h 15mnonstop
JetBlue Logo
4:22 pm - 5:33 pm
STI
-
SJU
1h 11mnonstop
$318JetBlue
Thu, Apr 16 - Fri, Apr 24
JetBlue Logo
1:57 pm - 3:12 pm
SJU
-
STI
1h 15mnonstop
JetBlue Logo
8:01 am - 5:49 pm
STI
-
SJU
9h 48m
1 stop
$319JetBlue
Fri, Apr 3 - Sun, Apr 12
Spirit Airlines Logo
12:55 pm - 1:49 am
SJU
-
STI
12h 54m
1 stop
Spirit Airlines Logo
2:46 am - 6:55 pm
STI
-
SJU
16h 09m
1 stop
$326Spirit Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$137
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from San Juan to Santiago de los Caballeros

FAQs for booking flights from Caribbean Islands to Santiago de los Caballeros

  • How does KAYAK find such low prices on flights from Caribbean Islands to Santiago de los Caballeros?

    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 Santiago de los Caballeros.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Santiago de los Caballeros 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 Santiago de los Caballeros?

    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 Santiago de los Caballeros 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 Santiago de los Caballeros?

    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 Santiago de los Caballeros 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 airlines flying from Caribbean Islands to Santiago de los Caballeros

 
Need help choosing which airline to fly with from Caribbean Islands to Santiago de los Caballeros? 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.
7.2
JetBlueOverall score based on 2906 reviews
7.2Entertainment
6.6Food
7.5Comfort
8.0Crew
7.4Boarding
Airline reviews

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

2.0 MediocreAnonymous, Mar 2026
RSW - BOS
Read more JetBlue reviews

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

The seats have so much room. They give great free snacks. Staff was so nice.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

Very smooth flight, good legroom with the "even more room" seats. Entertainment choice was excellent, wifi on board, plane was modern. Pilot got a round of applause for a smooth landing in very blustery conditions. Love flying with them. Check in was OK too. We were too early so we had to wait until groundstaff showed up 3hrs before the flight.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

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 Santiago de los Caballeros

Information on the airport you'll fly into in Santiago de los Caballeros