$253 Find Cheap Flights from Caribbean Islands to Valparaiso - 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 Valparaiso departing on 7/14. 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, 0 bags

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Cheap Flights from Caribbean Islands to Valparaiso

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

Thu, Aug 27 - Tue, Sep 1
Delta Logo
2:59 pm - 8:53 pm
SJU
-
VPS
6h 54m
1 stop
Delta Logo
12:00 pm - 10:29 pm
VPS
-
SJU
9h 29m
1 stop
$445Delta
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:24 pm - 11:52 pm
SJU
-
VPS
5h 28m
1 stop
American Airlines Logo
6:00 am - 9:55 pm
VPS
-
SJU
14h 55m
1 stop
$485American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:24 pm - 11:52 pm
SJU
-
VPS
5h 28m
1 stop
American Airlines Logo
6:54 pm - 12:40 pm
VPS
-
SJU
16h 46m
2 stops
$486American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:30 am - 8:03 pm
SJU
-
VPS
13h 33m
1 stop
American Airlines Logo
12:41 pm - 12:15 am
VPS
-
SJU
10h 34m
1 stop
$510American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:30 am - 8:03 pm
SJU
-
VPS
13h 33m
1 stop
American Airlines Logo
6:54 pm - 12:40 pm
VPS
-
SJU
16h 46m
2 stops
$511American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:24 pm - 11:52 pm
SJU
-
VPS
5h 28m
1 stop
American Airlines Logo
7:28 am - 6:33 pm
VPS
-
SJU
10h 05m
2 stops
$551American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
6:00 am - 8:03 pm
SJU
-
VPS
15h 03m
2 stops
American Airlines Logo
6:54 pm - 12:40 pm
VPS
-
SJU
16h 46m
2 stops
$626American Airlines
Tue, Nov 10 - Sat, Nov 14
WestJet Logo
5:30 pm - 11:07 pm
POP
-
VPS
31h 37m
2 stops
WestJet Logo
9:25 am - 4:33 pm
VPS
-
POP
29h 08m
2 stops
$1,819WestJet
Tue, Nov 10 - Sat, Nov 14
WestJet Logo
5:30 pm - 11:07 pm
POP
-
VPS
31h 37m
2 stops
WestJet Logo
9:25 am - 4:33 pm
VPS
-
POP
29h 08m
2 stops
$1,834WestJet
Tue, Nov 10 - Sat, Nov 14
WestJet Logo
5:30 pm - 11:07 pm
POP
-
VPS
31h 37m
2 stops
WestJet Logo
9:25 am - 4:33 pm
VPS
-
POP
29h 08m
2 stops
$1,843WestJet
Useful Info

Good to know

Most popular time to fly with an average 4% increase in price.

FAQs for booking flights from Caribbean Islands to Valparaiso

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

    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 Valparaiso.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Valparaiso 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 Valparaiso?

    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 Valparaiso 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 Valparaiso?

    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 Valparaiso 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 airline flying from Caribbean Islands to Valparaiso

 
Need help choosing which airline to fly with from Caribbean Islands to Valparaiso? 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.
7.1
American AirlinesOverall score based on 11766 reviews
6.8Entertainment
7.2Comfort
7.9Crew
6.4Food
7.5Boarding
Airline reviews

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

2.0 MediocreHolly, Jun 2026
ORD - MIA
Read more American Airlines reviews

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

We departed early and arrived early The plane was clean and the crew was incredibly efficient another positive experience with American airlines for me.

Departure down was really rough and ended up getting motion sickness on the flight

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