$167 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 3/5. 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
$346
Southwest
Thu 3/5Sun 3/8
SJU - VPS • 2 stops
Cheapest one-way
$167
Multiple Airlines
Thu 3/5
SJU - VPS • 2 stops
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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

Thu, Mar 5 - Sun, Mar 8
Southwest Logo
8:00 am - 3:20 pm
SJU
-
VPS
9h 20m2 stops
Southwest Logo
10:25 am - 1:40 am
VPS
-
SJU
14h 15m2 stops
$346Southwest
Thu, Mar 5 - Sun, Mar 8
Southwest Logo
6:30 am - 3:20 pm
SJU
-
VPS
10h 50m2 stops
Southwest Logo
2:00 pm - 12:05 am
VPS
-
SJU
9h 05m1 stop
$365Southwest
Tue, Feb 24 - Mon, Mar 2
Southwest Logo
5:40 am - 6:55 pm
SJU
-
VPS
15h 15m2 stops
Southwest Logo
7:10 am - 10:25 pm
VPS
-
SJU
13h 15m2 stops
$366Southwest
Tue, Jun 16 - Sun, Jun 21
Southwest Logo
6:30 am - 3:20 pm
SJU
-
VPS
9h 50m2 stops
Southwest Logo
7:25 am - 6:10 pm
VPS
-
SJU
9h 45m1 stop
$375Southwest
Tue, Feb 24 - Mon, Mar 2
American Airlines Logo
10:50 am - 10:15 pm
SJU
-
VPS
13h 25m2 stops
American Airlines Logo
7:42 am - 4:20 pm
VPS
-
SJU
6h 38m1 stop
$385American Airlines
Thu, Jan 22 - Sat, Jan 31
Southwest Logo
10:20 am - 6:55 pm
SJU
-
VPS
10h 35m2 stops
Southwest Logo
11:00 am - 12:10 am
VPS
-
SJU
11h 10m2 stops
$391Southwest
Fri, Feb 13 - Sun, Feb 15
American Airlines Logo
12:46 pm - 10:24 pm
SJU
-
VPS
11h 38m2 stops
American Airlines Logo
7:03 am - 11:31 pm
VPS
-
SJU
14h 28m1 stop
$405American Airlines
Wed, May 13 - Fri, Sep 18
American Airlines Logo
1:32 pm - 11:50 pm
STI
-
VPS
11h 18m1 stop
American Airlines Logo
6:00 am - 12:20 pm
VPS
-
STI
5h 20m1 stop
$587American Airlines
Wed, May 13 - Fri, Sep 18
American Airlines Logo
1:32 pm - 11:50 pm
STI
-
VPS
11h 18m1 stop
American Airlines Logo
4:57 pm - 12:20 pm
VPS
-
STI
18h 23m2 stops
$591American Airlines
Sat, Jan 31 - Wed, Feb 4
Delta Logo
6:38 am - 11:05 pm
STI
-
VPS
18h 27m2 stops
Delta Logo
6:00 am - 8:34 pm
VPS
-
STI
12h 34m2 stops
$652Delta
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 11111 reviews
6.4Food
7.5Boarding
6.9Entertainment
8.0Crew
7.2Comfort
Airline reviews

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

2.0 MediocreMary, Jan 2026
GCM - MIA
Read more American Airlines reviews

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

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.

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