$192 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 5/24. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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$587
Santo Domingo
Santo Domingo1 stop$541
Montego Bay
Montego Bay1 stop$351
Nassau
Nassau2 stops$461
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$671
St. John's
St. John's2 stops$3,629
Punta Cana
Punta Cana1 stop$587
Santo Domingo
Santo Domingo1 stop$541
Montego Bay
Montego Bay1 stop$351
Nassau
Nassau2 stops$461
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$671
St. John's
St. John's2 stops$3,629

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

Sun, Sep 6 - Fri, Sep 11
Delta Logo
7:45 am - 3:34 pm
VPS
-
MBJ
7h 49m
1 stop
Delta Logo
4:59 pm - 11:08 pm
MBJ
-
VPS
6h 09m
1 stop
$351Delta
Sun, Sep 6 - Fri, Sep 11
American Airlines Logo
7:27 pm - 1:50 pm
VPS
-
MBJ
18h 23m
2 stops
American Airlines Logo
1:05 pm - 11:58 pm
MBJ
-
VPS
10h 53m
1 stop
$355American Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
6:20 am - 3:37 pm
VPS
-
MBJ
9h 17m
1 stop
American Airlines Logo
12:56 pm - 11:50 pm
MBJ
-
VPS
10h 54m
1 stop
$386American Airlines
Thu, Jul 16 - Mon, Jul 20
Southwest Logo
2:00 pm - 12:15 am
VPS
-
SJU
9h 15m
1 stop
Southwest Logo
5:00 am - 1:20 pm
SJU
-
VPS
9h 20m
2 stops
$445Southwest
Wed, Jul 22 - Mon, Jul 27
Southwest Logo
12:05 pm - 11:45 pm
VPS
-
SJU
10h 40m
2 stops
Southwest Logo
5:00 am - 1:20 pm
SJU
-
VPS
9h 20m
2 stops
$460Southwest
Tue, Sep 1 - Sun, Sep 13
Delta Logo
7:45 am - 4:35 pm
VPS
-
SJU
7h 50m
1 stop
Delta Logo
5:41 pm - 11:08 pm
SJU
-
VPS
6h 27m
1 stop
$470Delta
Sat, May 30 - Sat, Jun 6
JetBlue Logo
3:59 pm - 3:36 am
VPS
-
SDQ
10h 37m
1 stop
JetBlue Logo
5:01 am - 3:04 pm
SDQ
-
VPS
11h 03m
1 stop
$541JetBlue
Mon, Jun 1 - Thu, Jun 4
JetBlue Logo
3:59 pm - 3:36 am
VPS
-
SDQ
10h 37m
1 stop
JetBlue Logo
3:10 am - 3:04 pm
SDQ
-
VPS
12h 54m
1 stop
$567JetBlue
Tue, Sep 22 - Fri, Sep 25
WestJet Logo
9:25 am - 2:30 pm
VPS
-
KIN
29h 05m
2 stops
WestJet Logo
3:30 pm - 1:29 pm
KIN
-
VPS
21h 59m
2 stops
$3,475WestJet
Tue, Sep 22 - Fri, Sep 25
WestJet Logo
9:25 am - 2:30 pm
VPS
-
KIN
29h 05m
2 stops
WestJet Logo
3:30 pm - 1:29 pm
KIN
-
VPS
21h 59m
2 stops
$3,476WestJet
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 $305, 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 May, when tickets cost $374 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is $648 and $624 respectively.

Good to know

Low seasonAugust
Cheapest flight$192
Most popular time to fly with an average 6% increase in price.
Flight from Valparaiso to Saint Thomas Island

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 8406 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
Airline reviews

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

2.0 MediocreGregory, Apr 2026
TPA - CVG
Read more Delta reviews

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

The flight attendant in business class was excellent! Professional, friendly and attentive.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports