$202 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 5/8. 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

Wed, Apr 29 - Tue, May 12
Southwest Logo
5:05 am - 1:10 pm
SJU
-
VPS
9h 05m
1 stop
Southwest Logo
2:00 pm - 10:40 pm
VPS
-
SJU
7h 40m
1 stop
$440Southwest
Wed, Apr 29 - Tue, May 12
Southwest Logo
5:05 am - 1:10 pm
SJU
-
VPS
9h 05m
1 stop
Southwest Logo
10:25 am - 10:40 pm
VPS
-
SJU
11h 15m
2 stops
$441Southwest
Wed, Apr 29 - Tue, May 12
Southwest Logo
11:25 am - 9:00 pm
SJU
-
VPS
10h 35m
2 stops
Southwest Logo
10:25 am - 11:40 pm
VPS
-
SJU
12h 15m
2 stops
$461Southwest
Wed, May 6 - Wed, May 13
Delta Logo
12:55 pm - 8:28 pm
SJU
-
VPS
8h 33m
1 stop
Delta Logo
9:15 am - 8:30 pm
VPS
-
SJU
10h 15m
1 stop
$475Delta
Wed, May 6 - Wed, May 6
American Airlines Logo
7:25 am - 4:06 pm
SJU
-
VPS
9h 41m
1 stop
American Airlines Logo
6:58 pm - 4:32 am
VPS
-
SJU
8h 34m
1 stop
$514American Airlines
Wed, May 13 - Wed, May 13
American Airlines Logo
7:25 am - 4:06 pm
SJU
-
VPS
9h 41m
1 stop
American Airlines Logo
6:58 pm - 4:32 am
VPS
-
SJU
8h 34m
1 stop
$524American Airlines
Sun, May 3 - Sat, May 9
Delta Logo
6:15 am - 4:00 pm
SJU
-
VPS
10h 45m
1 stop
Delta Logo
2:58 pm - 10:17 pm
VPS
-
SJU
6h 19m
1 stop
$565Delta
Wed, May 6 - Wed, May 6
American Airlines Logo
6:45 am - 2:31 pm
SJU
-
VPS
8h 46m
1 stop
American Airlines Logo
4:46 pm - 9:13 am
VPS
-
SJU
15h 27m
2 stops
$566American Airlines
Thu, Apr 16 - Mon, Apr 20
JetBlue Logo
5:01 am - 3:00 pm
SJU
-
VPS
10h 59m
1 stop
JetBlue Logo
9:59 am - 9:00 pm
VPS
-
SJU
10h 01m
1 stop
$672JetBlue
Fri, May 8 - Mon, May 11
JetBlue Logo
5:01 am - 3:04 pm
SDQ
-
VPS
11h 03m
1 stop
JetBlue Logo
3:59 pm - 1:54 am
VPS
-
SDQ
8h 55m
1 stop
$728JetBlue
Useful Info

Good to know

Most popular time to fly with an average 1% 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 11555 reviews
6.4Food
7.2Comfort
7.9Crew
6.9Entertainment
7.5Boarding
Airline reviews

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

2.0 MediocreSerena, Apr 2026
DCA - TPA
Read more American Airlines reviews

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Crew was rude, almost 6 hour flight after horrific customs re entry line and near flight miss (unable to bug airport food) without food offerings.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

An delay of almost 3 hours while passengers were already in the plane kept us very uncomfortable. The food was also very limited. A bad experience overall.

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

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