$182 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 5/15. 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$595
Santo Domingo
Santo Domingo1 stop$588
Montego Bay
Montego Bay2 stops$355
Oranjestad
Oranjestad2 stops$3,655
Nassau
Nassau2 stops$426
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$666
George Town
George Town1 stop$735
Willemstad
Willemstad2 stops$662
Punta Cana
Punta Cana1 stop$595
Santo Domingo
Santo Domingo1 stop$588
Montego Bay
Montego Bay2 stops$355
Oranjestad
Oranjestad2 stops$3,655
Nassau
Nassau2 stops$426
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$666
George Town
George Town1 stop$735
Willemstad
Willemstad2 stops$662

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, Jul 19 - Tue, Aug 4
American Airlines Logo
6:37 pm - 11:47 am
VPS
-
MBJ
17h 10m
2 stops
American Airlines Logo
5:17 pm - 11:42 am
MBJ
-
VPS
18h 25m
2 stops
$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
4:37 pm - 11:50 pm
MBJ
-
VPS
7h 13m
1 stop
$386American Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
4:46 pm - 3:37 pm
VPS
-
MBJ
22h 51m
2 stops
American Airlines Logo
4:37 pm - 11:50 pm
MBJ
-
VPS
7h 13m
1 stop
$390American Airlines
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
10:58 am - 10:18 am
VPS
-
SJU
22h 20m
2 stops
Multiple Airlines Logo
12:59 am - 1:50 pm
SJU
-
VPS
13h 51m
1 stop
$410Multiple Airlines
Tue, May 5 - Tue, May 12
Southwest Logo
2:00 pm - 10:40 pm
VPS
-
SJU
7h 40m
1 stop
Southwest Logo
5:05 am - 1:10 pm
SJU
-
VPS
9h 05m
1 stop
$415Southwest
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
7:15 am - 6:30 pm
VPS
-
NAS
10h 15m
2 stops
Southwest Logo
8:45 am - 9:20 pm
NAS
-
VPS
13h 35m
2 stops
$426Southwest
Tue, Sep 1 - Sun, Sep 13
Delta Logo
6:00 am - 4:35 pm
VPS
-
SJU
9h 35m
1 stop
Delta Logo
5:41 pm - 11:08 pm
SJU
-
VPS
6h 27m
1 stop
$470Delta
Thu, Jun 18 - Sun, Jun 21
Delta Logo
9:19 am - 8:43 pm
VPS
-
SJU
10h 24m
1 stop
Delta Logo
5:56 pm - 11:32 pm
SJU
-
VPS
6h 36m
1 stop
$505Delta
Mon, Apr 27 - Fri, May 1
JetBlue Logo
9:59 am - 1:19 am
VPS
-
SDQ
14h 20m
1 stop
JetBlue Logo
7:26 pm - 9:08 am
SDQ
-
VPS
14h 42m
1 stop
$588JetBlue
Fri, May 29 - Thu, Jun 4
JetBlue Logo
3:59 pm - 1:59 pm
VPS
-
CUR
21h 00m
2 stops
JetBlue Logo
3:04 pm - 3:04 pm
CUR
-
VPS
25h 00m
2 stops
$662JetBlue
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 $318, 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$182
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
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2026
MIA - DTW
Read more Delta reviews

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.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

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.

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

It was great. Smooth flight, comfortable, left on time and landed on time.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports