$190 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 5/29. 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 4 - Mon, Sep 7
Southwest Logo
5:00 am - 1:15 pm
SJU
-
VPS
9h 15m
2 stops
Southwest Logo
12:40 pm - 11:50 pm
VPS
-
SJU
10h 10m
2 stops
$446Southwest
Thu, Sep 3 - Mon, Sep 7
Southwest Logo
5:30 am - 1:15 pm
SJU
-
VPS
8h 45m
1 stop
Southwest Logo
12:40 pm - 11:50 pm
VPS
-
SJU
10h 10m
2 stops
$456Southwest
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
1:38 pm - 11:51 pm
SJU
-
VPS
11h 13m
1 stop
American Airlines Logo
7:01 am - 11:59 pm
VPS
-
SJU
15h 58m
1 stop
$468American Airlines
Fri, Sep 4 - Mon, Sep 7
Delta Logo
2:40 pm - 11:08 pm
SJU
-
VPS
9h 28m
1 stop
Delta Logo
6:00 am - 4:35 pm
VPS
-
SJU
9h 35m
1 stop
$475Delta
Thu, Sep 3 - Mon, Sep 7
Southwest Logo
5:00 am - 1:15 pm
SJU
-
VPS
9h 15m
2 stops
Southwest Logo
12:40 pm - 11:50 pm
VPS
-
SJU
10h 10m
2 stops
$525Southwest
Tue, Jun 30 - Mon, Jul 6
Delta Logo
6:02 pm - 11:10 pm
NAS
-
VPS
6h 08m
1 stop
Delta Logo
6:00 am - 4:37 pm
VPS
-
NAS
9h 37m
1 stop
$527Delta
Tue, Jun 30 - Mon, Jul 6
American Airlines Logo
1:32 pm - 11:47 pm
NAS
-
VPS
11h 15m
1 stop
American Airlines Logo
6:00 am - 3:09 pm
VPS
-
NAS
8h 09m
1 stop
$534American Airlines
Tue, Jun 30 - Mon, Jul 6
American Airlines Logo
2:55 pm - 11:47 pm
NAS
-
VPS
9h 52m
1 stop
American Airlines Logo
4:53 pm - 9:27 am
VPS
-
NAS
15h 34m
2 stops
$539American Airlines
Tue, Jun 2 - Wed, Jun 17
JetBlue Logo
6:15 am - 12:27 pm
SJU
-
VPS
7h 12m
1 stop
JetBlue Logo
9:19 am - 4:46 pm
VPS
-
SJU
6h 27m
1 stop
$574JetBlue
Wed, Jun 3 - Mon, Jun 8
JetBlue Logo
3:11 am - 3:03 pm
SDQ
-
VPS
12h 52m
1 stop
JetBlue Logo
3:59 pm - 3:36 am
VPS
-
SDQ
10h 37m
1 stop
$607JetBlue
Useful Info

Good to know

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 11669 reviews
7.2Comfort
6.4Food
7.5Boarding
7.9Crew
6.9Entertainment
Airline reviews

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.

6.0 GoodMiguel, May 2026
MAD - MIA
Read more American Airlines reviews

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.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

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