$208 Find Cheap Flights from Caribbean Islands to Valparaiso

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 9/24. 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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Flight Deals

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

Fri, Sep 25 - Mon, Oct 5
Southwest Logo
6:30 am - 3:25 pm
SJU
-
VPS
9h 55m
2 stops
Southwest Logo
4:40 pm - 12:35 am
VPS
-
SJU
6h 55m
1 stop
$415Southwest
Fri, Sep 25 - Sun, Oct 4
Southwest Logo
5:30 am - 1:15 pm
SJU
-
VPS
8h 45m
1 stop
Southwest Logo
12:40 pm - 11:35 pm
VPS
-
SJU
9h 55m
2 stops
$416Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
5:30 am - 1:15 pm
SJU
-
VPS
8h 45m
1 stop
Southwest Logo
12:05 pm - 11:50 pm
VPS
-
SJU
10h 45m
1 stop
$425Southwest
Thu, Sep 24 - Sun, Oct 4
Delta Logo
12:58 pm - 6:29 pm
SJU
-
VPS
6h 31m
1 stop
Delta Logo
6:00 am - 1:16 pm
VPS
-
SJU
6h 16m
1 stop
$445Delta
Thu, Sep 24 - Sun, Oct 4
American Airlines Logo
6:30 am - 9:00 pm
SJU
-
VPS
15h 30m
2 stops
American Airlines Logo
4:57 pm - 11:05 am
VPS
-
SJU
17h 08m
2 stops
$446American Airlines
Thu, Jun 4 - Mon, Jun 8
JetBlue Logo
8:06 pm - 9:06 am
SJU
-
VPS
14h 00m
1 stop
JetBlue Logo
9:59 am - 1:38 am
VPS
-
SJU
14h 39m
1 stop
$469JetBlue
Wed, Jun 3 - Mon, Jun 8
JetBlue Logo
3:30 am - 9:06 am
SJU
-
VPS
30h 36m
1 stop
JetBlue Logo
9:59 am - 8:58 am
VPS
-
SJU
21h 59m
1 stop
$524JetBlue
Tue, Jun 30 - Mon, Jul 6
Delta Logo
3:29 pm - 11:10 pm
NAS
-
VPS
8h 41m
1 stop
Delta Logo
6:00 am - 4:37 pm
VPS
-
NAS
9h 37m
1 stop
$587Delta
Tue, Jun 30 - Mon, Jul 6
American Airlines Logo
6:40 pm - 11:47 pm
NAS
-
VPS
6h 07m
1 stop
American Airlines Logo
6:37 pm - 12:41 pm
VPS
-
NAS
17h 04m
2 stops
$599American Airlines
Thu, Oct 29 - Mon, Nov 2
WestJet Logo
4:30 pm - 6:28 pm
POP
-
VPS
26h 58m
2 stops
WestJet Logo
6:00 am - 4:33 pm
VPS
-
POP
32h 33m
2 stops
$1,926WestJet
Useful Info

Good to know

Most popular time to fly and prices are also 12% lower on average.

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 11631 reviews
7.5Boarding
6.4Food
7.9Crew
7.2Comfort
6.9Entertainment
Airline reviews

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

8.0 ExcellentMichael, May 2026
CLT - MCO
Read more American Airlines reviews

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Poor... food was horrible, boarding very slow, service on board mediocre

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Departed late but made up the time en route. Uncrowded and clean aircraft.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

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