$197 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 1/6. 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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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 Cana2 stops$519
Santo Domingo
Santo Domingo1 stop$897
Montego Bay
Montego Bay1 stop$530
Oranjestad
Oranjestad1 stop$553
Nassau
Nassau1 stop$473
Kingston
Kingston1 stop$583
Simpson Bay
Simpson Bay1 stop$613
St. John's
St. John's1 stop$601
Punta Cana
Punta Cana2 stops$519
Santo Domingo
Santo Domingo1 stop$897
Montego Bay
Montego Bay1 stop$530
Oranjestad
Oranjestad1 stop$553
Nassau
Nassau1 stop$473
Kingston
Kingston1 stop$583
Simpson Bay
Simpson Bay1 stop$613
St. John's
St. John's1 stop$601

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, Jan 22 - Tue, Jan 27
Southwest Logo
7:00 am - 11:10 pm
VPS
-
SJU
14h 10m2 stops
Southwest Logo
6:00 am - 6:55 pm
SJU
-
VPS
14h 55m2 stops
$344Southwest
Fri, Feb 20 - Tue, Feb 24
Southwest Logo
12:00 pm - 1:35 am
VPS
-
SJU
11h 35m2 stops
Southwest Logo
5:40 am - 6:55 pm
SJU
-
VPS
15h 15m2 stops
$364Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
11:05 am - 9:25 pm
VPS
-
SJU
9h 20m2 stops
Southwest Logo
5:15 am - 1:15 pm
SJU
-
VPS
9h 00m1 stop
$374Southwest
Thu, Feb 19 - Tue, Feb 24
American Airlines Logo
7:42 am - 11:34 pm
VPS
-
SJU
13h 52m2 stops
American Airlines Logo
12:46 pm - 11:59 pm
SJU
-
VPS
13h 13m1 stop
$384American Airlines
Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
11:31 am - 10:26 pm
VPS
-
SJU
8h 55m1 stop
American Airlines Logo
8:20 am - 4:30 pm
SJU
-
VPS
10h 10m1 stop
$404American Airlines
Wed, Feb 25 - Mon, Mar 2
American Airlines Logo
6:00 am - 1:33 pm
VPS
-
SJU
5h 33m1 stop
American Airlines Logo
4:01 pm - 11:18 pm
SJU
-
VPS
9h 17m1 stop
$414American Airlines
Sun, Jan 11 - Thu, Jan 15
Multiple Airlines Logo
6:32 pm - 4:08 pm
VPS
-
SJU
19h 36m1 stop
Multiple Airlines Logo
6:00 am - 7:08 pm
SJU
-
VPS
39h 08m2 stops
$441Multiple Airlines
Tue, Jan 27 - Thu, Feb 5
Delta Logo
6:00 am - 12:54 pm
VPS
-
MBJ
5h 54m1 stop
Delta Logo
4:45 pm - 11:05 pm
MBJ
-
VPS
7h 20m1 stop
$540Delta
Sat, Jan 24 - Fri, Jan 30
Delta Logo
5:56 pm - 12:30 pm
VPS
-
AUA
16h 34m1 stop
Delta Logo
4:35 pm - 11:05 pm
AUA
-
VPS
8h 30m1 stop
$553Delta
Thu, Apr 9 - Sun, Apr 12
JetBlue Logo
3:55 pm - 3:54 am
VPS
-
SDQ
10h 59m1 stop
JetBlue Logo
4:30 am - 3:00 pm
SDQ
-
VPS
11h 30m1 stop
$897JetBlue
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 $320, 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 January, when tickets cost $358 (return) on average. On the other hand, the most expensive months are February and November, when the average cost of round-trip tickets is $680 and $648 respectively.

What’s the cheapest day of the week to fly from Valparaiso to Caribbean Islands?

The average price of all round-trip flights from Valparaiso to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Valparaiso to Caribbean Islands, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Valparaiso, you’ll find the best rates on Fridays and the most expensive ones on Wednesdays.

Good to know

Low seasonAugust
Cheapest flight$196
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Valparaiso to San Juan

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 8014 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.3Food
7.9Entertainment
Airline reviews

The food is terrible. The staff is wonderful. Comfort is good.

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports