$258 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 4/25. 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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Everything you should know

Cheapest round-trip
$345
Southwest
Fri 2/13Tue 2/17
SJU - VPS • 2 stops
Cheapest one-way
$258
American Airlines
Sat 4/25
SJU - VPS • 1 stop
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Flight Deals
Useful Info
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, Feb 13 - Tue, Feb 17
Southwest Logo
6:30 am - 9:10 pm
SJU
-
VPS
16h 40m2 stops
Southwest Logo
11:15 am - 12:40 am
VPS
-
SJU
11h 25m2 stops
$345Southwest
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
12:45 pm - 11:53 pm
SJU
-
VPS
13h 08m1 stop
American Airlines Logo
6:00 am - 3:46 pm
VPS
-
SJU
7h 46m1 stop
$375American Airlines
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
10:57 am - 11:53 pm
SJU
-
VPS
14h 56m1 stop
American Airlines Logo
4:39 pm - 10:07 am
VPS
-
SJU
15h 28m2 stops
$376American Airlines
Tue, Dec 23 - Wed, Dec 31
Southwest Logo
11:35 am - 9:10 pm
SJU
-
VPS
11h 35m2 stops
Southwest Logo
7:15 am - 9:30 pm
VPS
-
SJU
12h 15m2 stops
$400Southwest
Wed, Jan 14 - Thu, Jan 22
American Airlines Logo
6:00 am - 3:15 pm
SJU
-
VPS
11h 15m2 stops
American Airlines Logo
6:00 am - 11:59 pm
VPS
-
SJU
15h 59m1 stop
$404American Airlines
Wed, Jan 14 - Thu, Jan 22
American Airlines Logo
6:00 am - 9:00 pm
SJU
-
VPS
17h 00m2 stops
American Airlines Logo
11:00 am - 11:59 pm
VPS
-
SJU
10h 59m2 stops
$405American Airlines
Thu, Feb 12 - Tue, Feb 17
American Airlines Logo
7:00 pm - 11:53 pm
SJU
-
VPS
6h 53m1 stop
American Airlines Logo
6:00 am - 1:36 pm
VPS
-
SJU
5h 36m1 stop
$472American Airlines
Tue, Dec 23 - Wed, Dec 31
American Airlines Logo
12:47 pm - 11:17 pm
SJU
-
VPS
12h 30m2 stops
American Airlines Logo
6:50 am - 11:27 pm
VPS
-
SJU
14h 37m1 stop
$484American Airlines
Sat, Jan 31 - Tue, Feb 3
WestJet Logo
6:15 pm - 4:05 pm
NAS
-
VPS
22h 50m2 stops
WestJet Logo
6:00 am - 5:17 pm
VPS
-
NAS
34h 17m2 stops
$1,600WestJet
Wed, Jan 21 - Sun, Jan 25
WestJet Logo
5:30 pm - 12:59 pm
POP
-
VPS
45h 29m2 stops
WestJet Logo
5:05 pm - 4:33 pm
VPS
-
POP
45h 28m2 stops
$1,700WestJet
Useful Info

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.
7.2
American AirlinesOverall score based on 11047 reviews
6.5Food
7.2Comfort
7.5Boarding
6.9Entertainment
8.0Crew
Airline reviews

Attendants were pleasant and the flight was smooth and relaxed.

10.0 ExcellentDawn C, Dec 2025
DFW - MIA
Read more American Airlines reviews

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

The delayed flight was awful and moving the departure gate twice was annoying

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Traveling to a place near Valparaiso?

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Everything you need to know for your flight to Valparaiso

Information on the airport you'll fly into in Valparaiso

Valparaiso (VPS)