$186 Find Cheap Flights from Valparaiso to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Valparaiso to Caribbean Islands departing on 7/26. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Valparaiso to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Valparaiso to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Valparaiso to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$630
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad1 stop$674
Nassau
Nassau1 stop$496
Simpson Bay
Simpson Bay1 stop$676
George Town
George Town1 stop$665
Willemstad
Willemstad1 stop$1,046
St. John's
St. John's1 stop$1,090
Punta Cana
Punta Cana1 stop$630
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad1 stop$674
Nassau
Nassau1 stop$496
Simpson Bay
Simpson Bay1 stop$676
George Town
George Town1 stop$665
Willemstad
Willemstad1 stop$1,046
St. John's
St. John's1 stop$1,090

Book Cheap Valparaiso to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Valparaiso to Caribbean Islands 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 Valparaiso to Caribbean Islands

Wed, Sep 9 - Wed, Sep 16
Southwest Logo
7:15 am - 9:05 pm
VPS
-
SJU
12h 50m
2 stops
Southwest Logo
11:50 am - 9:05 pm
SJU
-
VPS
10h 15m
2 stops
$415Southwest
Thu, Aug 13 - Wed, Aug 19
JetBlue Logo
9:59 am - 12:10 am
VPS
-
SJU
13h 11m
1 stop
JetBlue Logo
9:10 pm - 9:00 am
SJU
-
VPS
12h 50m
1 stop
$421JetBlue
Fri, Aug 28 - Mon, Aug 31
American Airlines Logo
6:00 am - 11:42 am
VPS
-
MBJ
5h 42m
1 stop
American Airlines Logo
5:08 pm - 11:51 am
MBJ
-
VPS
18h 43m
2 stops
$425American Airlines
Mon, Jul 13 - Sun, Aug 2
American Airlines Logo
4:53 pm - 11:47 am
VPS
-
MBJ
18h 54m
2 stops
American Airlines Logo
5:14 pm - 12:20 pm
MBJ
-
VPS
19h 06m
2 stops
$430American Airlines
Tue, Sep 1 - Sun, Sep 13
American Airlines Logo
7:01 am - 11:59 pm
VPS
-
SJU
15h 58m
1 stop
American Airlines Logo
6:27 am - 9:55 pm
SJU
-
VPS
16h 28m
2 stops
$445American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
5:45 am - 3:40 pm
VPS
-
SJU
8h 55m
1 stop
American Airlines Logo
2:58 pm - 11:00 pm
SJU
-
VPS
9h 02m
1 stop
$450American Airlines
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
7:15 am - 6:25 pm
VPS
-
SJU
10h 10m
2 stops
Southwest Logo
5:30 am - 3:15 pm
SJU
-
VPS
10h 45m
2 stops
$455Southwest
Thu, Jul 16 - Wed, Jul 22
American Airlines Logo
12:47 pm - 10:59 pm
VPS
-
SJU
9h 12m
1 stop
American Airlines Logo
7:14 pm - 11:59 pm
SJU
-
VPS
5h 45m
1 stop
$465American Airlines
Wed, Sep 2 - Sun, Sep 6
Delta Logo
6:00 am - 1:53 pm
VPS
-
SXM
6h 53m
1 stop
Delta Logo
3:18 pm - 9:44 pm
SXM
-
VPS
7h 26m
1 stop
$676Delta
Thu, Jul 23 - Wed, Jul 29
Delta Logo
7:00 am - 3:20 pm
VPS
-
STT
7h 20m
1 stop
Delta Logo
3:33 pm - 11:29 pm
STT
-
VPS
8h 56m
1 stop
$729Delta
Booking Insights

KAYAK's insights & trends for Valparaiso to Caribbean Islands flights

Get data-powered insights and trends into flights from Valparaiso to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Valparaiso to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $286, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Valparaiso to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Valparaiso to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Valparaiso to Caribbean Islands is April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $668 and $594 respectively.

Good to know

Low seasonAugust
Cheapest flight$186
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Valparaiso to Montego Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Valparaiso to Caribbean Islands?

    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 Valparaiso to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Valparaiso to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Valparaiso to 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 Valparaiso to Caribbean Islands?

    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 from Valparaiso to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Valparaiso to Caribbean Islands?

    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 from Valparaiso to 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 airlines flying from Valparaiso to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Valparaiso to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Valparaiso to Caribbean Islands? 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.
7.9
DeltaOverall score based on 8398 reviews
7.2Food
7.8Entertainment
8.1Boarding
7.8Comfort
8.5Crew
Airline reviews

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

8.0 ExcellentAnonymous, Jun 2026
TPA - LGA
Read more Delta reviews

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports