$261 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 12/4. 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$559
Santo Domingo
Santo Domingo1 stop$626
Montego Bay
Montego Bay1 stop$530
Oranjestad
Oranjestad1 stop$632
Kingston
Kingston1 stop$622
Simpson Bay
Simpson Bay1 stop$648
George Town
George Town1 stop$479
Willemstad
Willemstad1 stop$498
St. John's
St. John's1 stop$720
Punta Cana
Punta Cana1 stop$559
Santo Domingo
Santo Domingo1 stop$626
Montego Bay
Montego Bay1 stop$530
Oranjestad
Oranjestad1 stop$632
Kingston
Kingston1 stop$622
Simpson Bay
Simpson Bay1 stop$648
George Town
George Town1 stop$479
Willemstad
Willemstad1 stop$498
St. John's
St. John's1 stop$720

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, Apr 24 - Sat, May 2
Southwest Logo
12:35 pm - 11:40 pmVPS-SJU
10h 05m2 stops
Southwest Logo
1:45 pm - 9:00 pmSJU-VPS
8h 15m1 stop
$344Southwest
Find Deal
Sat, Feb 21 - Wed, Feb 25
American Airlines Logo
4:40 pm - 11:42 amVPS-SJU
17h 02m1 stop
American Airlines Logo
2:31 pm - 10:22 pmSJU-VPS
9h 51m2 stops
$364American Airlines
Find Deal
Sat, Jan 24 - Sun, Feb 1
Southwest Logo
7:25 am - 9:30 pmVPS-SJU
12h 05m2 stops
Southwest Logo
7:00 am - 9:15 pmSJU-VPS
16h 15m2 stops
$374Southwest
Find Deal
Tue, Dec 30 - Tue, Jan 13
American Airlines Logo
7:39 am - 10:05 pmVPS-SJU
12h 26m1 stop
American Airlines Logo
3:49 pm - 9:00 pmSJU-VPS
7h 11m1 stop
$384American Airlines
Find Deal
Sat, Apr 25 - Fri, May 1
JetBlue Logo
9:59 am - 8:20 pmVPS-SJU
9h 21m1 stop
JetBlue Logo
3:30 am - 3:01 pmSJU-VPS
12h 31m2 stops
$393JetBlue
Find Deal
Fri, Apr 24 - Fri, May 1
JetBlue Logo
9:59 am - 10:47 pmVPS-SJU
11h 48m1 stop
JetBlue Logo
3:30 am - 3:01 pmSJU-VPS
12h 31m2 stops
$407JetBlue
Find Deal
Sun, Feb 22 - Thu, Feb 26
Delta Logo
6:00 am - 2:45 pmVPS-CUR
6h 45m1 stop
Delta Logo
4:10 pm - 11:05 pmCUR-VPS
8h 55m1 stop
$498Delta
Find Deal
Sun, Mar 29 - Wed, Apr 1
Delta Logo
7:45 am - 2:15 pmVPS-POP
5h 30m1 stop
Delta Logo
3:35 pm - 11:08 pmPOP-VPS
8h 33m1 stop
$516Delta
Find Deal
Wed, Apr 8 - Thu, Apr 16
Multiple Airlines Logo
6:18 pm - 1:45 pmVPS-CUR
42h 27m3 stops
Multiple Airlines Logo
3:40 pm - 5:18 pmCUR-VPS
26h 38m3 stops
$1,166Multiple Airlines
Find Deal
Fri, Dec 19 - Mon, Jan 5
Multiple Airlines Logo
11:26 am - 12:14 pmVPS-KIN
23h 48m3 stops
Multiple Airlines Logo
1:19 pm - 11:11 pmKIN-VPS
10h 52m2 stops
$1,310Multiple Airlines
Find Deal
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 $298, 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 $352 (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$261
Most popular time to fly with an average 5% increase in price.
Flight from Valparaiso to San Juan Airport

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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $337 on average. Morning departures are around 28% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $503.

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 8007 reviews
7.9Comfort
8.5Crew
7.9Entertainment
8.1Boarding
7.3Food
Airline reviews

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.

10.0 ExcellentDuane, Nov 2025PBI - ATL
Read more Delta reviews

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.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

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

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports