$206 Find Cheap Flights from Valparaiso to Caribbean Islands - Compare and Save

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 8/31. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
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$639
Santo Domingo
Santo Domingo1 stop$569
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$664
Nassau
Nassau2 stops$557
Kingston
Kingston1 stop$684
Simpson Bay
Simpson Bay2 stops$690
George Town
George Town1 stop$680
Punta Cana
Punta Cana1 stop$639
Santo Domingo
Santo Domingo1 stop$569
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$664
Nassau
Nassau2 stops$557
Kingston
Kingston1 stop$684
Simpson Bay
Simpson Bay2 stops$690
George Town
George Town1 stop$680

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

Thu, Sep 10 - Thu, Sep 17
Southwest Logo
2:00 pm - 11:55 pm
VPS
-
SJU
8h 55m
2 stops
Southwest Logo
5:00 am - 1:15 pm
SJU
-
VPS
9h 15m
2 stops
$399Southwest
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
2:00 pm - 11:55 pm
VPS
-
SJU
8h 55m
2 stops
Southwest Logo
5:30 am - 1:15 pm
SJU
-
VPS
8h 45m
1 stop
$399Southwest
Tue, Aug 18 - Wed, Sep 2
Southwest Logo
7:15 am - 6:10 pm
VPS
-
SJU
9h 55m
2 stops
Southwest Logo
6:00 am - 1:30 pm
SJU
-
VPS
8h 30m
1 stop
$399Southwest
Tue, Aug 18 - Wed, Sep 2
Southwest Logo
7:15 am - 6:10 pm
VPS
-
SJU
9h 55m
2 stops
Southwest Logo
10:30 am - 9:05 pm
SJU
-
VPS
11h 35m
2 stops
$399Southwest
Thu, Aug 20 - Thu, Aug 27
American Airlines Logo
4:50 pm - 1:49 pm
VPS
-
MBJ
20h 59m
2 stops
American Airlines Logo
5:08 pm - 11:52 pm
MBJ
-
VPS
6h 44m
1 stop
$465American Airlines
Thu, Aug 20 - Thu, Aug 27
American Airlines Logo
5:59 pm - 11:42 am
VPS
-
MBJ
17h 43m
2 stops
American Airlines Logo
5:08 pm - 11:51 am
MBJ
-
VPS
18h 43m
2 stops
$465American Airlines
Thu, Sep 17 - Mon, Sep 21
Delta Logo
7:13 pm - 12:26 pm
VPS
-
STI
16h 13m
2 stops
Delta Logo
7:30 pm - 10:55 am
STI
-
VPS
16h 25m
2 stops
$479Delta
Thu, Sep 17 - Mon, Sep 21
Delta Logo
7:13 pm - 12:26 pm
VPS
-
STI
16h 13m
2 stops
Delta Logo
7:30 pm - 10:55 am
STI
-
VPS
16h 25m
2 stops
$489Delta
Tue, Dec 1 - Tue, Dec 8
Delta Logo
7:00 am - 5:25 pm
VPS
-
SJU
8h 25m
1 stop
Delta Logo
1:55 pm - 11:20 pm
SJU
-
VPS
11h 25m
1 stop
$495Delta
Tue, Sep 1 - Sun, Sep 13
American Airlines Logo
7:01 am - 2:51 pm
VPS
-
SJU
6h 50m
1 stop
American Airlines Logo
10:16 am - 11:43 pm
SJU
-
VPS
14h 27m
1 stop
$516American Airlines
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 $300, 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 November, when the average cost of round-trip tickets is $891 and $852 respectively.

Good to know

Low season

August

Cheapest flight

$206
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 11% 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.
7.8
DeltaOverall score based on 8482 reviews
7.2Food
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
Airline reviews

Boarding was quick and i made my connection early due to early arrival time

10.0 ExcellentKalen, Jul 2026
TPA - ATL
Read more Delta reviews

Boarding was quick and i made my connection early due to early arrival time

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

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.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

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

This leg they tried and did well with what they had to work from.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports