$157 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 6/1. 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$608
Santo Domingo
Santo Domingo2 stops$562
Montego Bay
Montego Bay1 stop$386
Oranjestad
Oranjestad1 stop$635
Nassau
Nassau1 stop$534
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$636
George Town
George Town1 stop$625
St. John's
St. John's1 stop$764
Punta Cana
Punta Cana1 stop$608
Santo Domingo
Santo Domingo2 stops$562
Montego Bay
Montego Bay1 stop$386
Oranjestad
Oranjestad1 stop$635
Nassau
Nassau1 stop$534
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$636
George Town
George Town1 stop$625
St. John's
St. John's1 stop$764

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

Fri, May 8 - Tue, May 12
Delta Logo
6:00 am - 3:34 pm
VPS
-
MBJ
9h 34m
1 stop
Delta Logo
2:21 pm - 11:13 pm
MBJ
-
VPS
8h 52m
1 stop
$386Delta
Fri, May 8 - Tue, May 12
American Airlines Logo
6:58 pm - 3:37 pm
VPS
-
MBJ
20h 39m
2 stops
American Airlines Logo
4:37 pm - 10:57 am
MBJ
-
VPS
18h 20m
2 stops
$390American Airlines
Fri, Sep 18 - Thu, Sep 24
Southwest Logo
12:40 pm - 11:50 pm
VPS
-
SJU
10h 10m
2 stops
Southwest Logo
6:00 am - 3:25 pm
SJU
-
VPS
10h 25m
2 stops
$415Southwest
Fri, Apr 17 - Fri, Apr 24
Southwest Logo
12:35 pm - 11:25 pm
VPS
-
SJU
9h 50m
2 stops
Southwest Logo
5:05 am - 3:20 pm
SJU
-
VPS
11h 15m
2 stops
$420Southwest
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
4:46 pm - 10:53 am
VPS
-
SJU
17h 07m
2 stops
American Airlines Logo
7:25 am - 9:35 pm
SJU
-
VPS
15h 10m
1 stop
$430American Airlines
Mon, Apr 27 - Fri, May 1
Delta Logo
6:00 am - 12:54 pm
VPS
-
MBJ
6h 54m
1 stop
Delta Logo
2:10 pm - 8:28 pm
MBJ
-
VPS
6h 18m
1 stop
$484Delta
Mon, Jun 1 - Sat, Jun 6
JetBlue Logo
3:59 pm - 10:38 am
VPS
-
PUJ
17h 39m
1 stop
JetBlue Logo
12:09 pm - 9:06 am
PUJ
-
VPS
21h 57m
1 stop
$650JetBlue
Fri, Jun 12 - Sat, Jun 20
JetBlue Logo
9:59 am - 3:42 pm
VPS
-
STT
28h 43m
2 stops
JetBlue Logo
2:00 pm - 3:00 pm
STT
-
VPS
26h 00m
2 stops
$660JetBlue
Wed, May 6 - Wed, Jun 10
WestJet Logo
2:25 pm - 11:45 am
VPS
-
MBJ
21h 20m
2 stops
WestJet Logo
12:45 pm - 12:31 pm
MBJ
-
VPS
23h 46m
2 stops
$3,376WestJet
Sun, May 10 - Sun, May 17
WestJet Logo
2:01 pm - 11:45 am
VPS
-
MBJ
21h 44m
2 stops
WestJet Logo
7:30 pm - 10:22 am
MBJ
-
VPS
14h 52m
2 stops
$3,478WestJet
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 $321, 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$157
Most popular time to fly with an average 5% increase in price.
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 8356 reviews
8.1Boarding
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

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.

6.0 GoodAnonymous, Mar 2026
PBI - LGA
Read more Delta reviews

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 flight was great as well as the airline staff

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.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports