$237 Find Cheap Flights from Valparaiso to Caribbean

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 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

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Cheap Flights from Valparaiso to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$504
Santo Domingo
Santo Domingo2 stops$506
Montego Bay
Montego Bay1 stop$573
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau1 stop$450
Kingston
Kingston1 stop$573
Simpson Bay
Simpson Bay1 stop$648
George Town
George Town1 stop$504
Willemstad
Willemstad2 stops$648
St. John's
St. John's2 stops$738
Punta Cana
Punta Cana2 stops$504
Santo Domingo
Santo Domingo2 stops$506
Montego Bay
Montego Bay1 stop$573
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau1 stop$450
Kingston
Kingston1 stop$573
Simpson Bay
Simpson Bay1 stop$648
George Town
George Town1 stop$504
Willemstad
Willemstad2 stops$648
St. John's
St. John's2 stops$738

Book Cheap Valparaiso to Caribbean 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 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

Wed, Apr 22 - Sun, Apr 26
Southwest Logo
7:15 am - 6:10 pmVPS-SJU
9h 55m2 stops
Southwest Logo
5:00 am - 1:15 pmSJU-VPS
9h 15m1 stop
$344Southwest
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Sun, Mar 1 - Thu, Mar 5
Delta Logo
4:20 pm - 11:49 pmVPS-SJU
5h 29m1 stop
Delta Logo
6:15 am - 12:57 pmSJU-VPS
8h 42m1 stop
$364Delta
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Mon, Mar 23 - Fri, Mar 27
Southwest Logo
7:20 am - 10:50 pmVPS-SJU
14h 30m2 stops
Southwest Logo
5:30 am - 5:15 pmSJU-VPS
12h 45m2 stops
$374Southwest
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Thu, Feb 19 - Tue, Feb 24
American Airlines Logo
7:40 am - 11:27 pmVPS-SJU
13h 47m2 stops
American Airlines Logo
2:31 pm - 10:22 pmSJU-VPS
9h 51m2 stops
$384American Airlines
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Thu, Feb 19 - Tue, Feb 24
American Airlines Logo
7:40 am - 11:27 pmVPS-SJU
13h 47m2 stops
American Airlines Logo
8:30 am - 3:55 pmSJU-VPS
9h 25m1 stop
$404American Airlines
Find Deal
Fri, Feb 20 - Tue, Feb 24
American Airlines Logo
6:00 am - 11:27 pmVPS-SJU
15h 27m1 stop
American Airlines Logo
7:00 am - 6:51 pmSJU-VPS
13h 51m2 stops
$414American Airlines
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Tue, Nov 18 - Thu, Dec 4
American Airlines Logo
4:57 pm - 3:47 pmVPS-SJU
20h 50m2 stops
American Airlines Logo
3:41 pm - 9:24 pmSJU-VPS
7h 43m1 stop
$424American Airlines
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Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:00 am - 1:15 pmVPS-SDQ
6h 15m1 stop
Delta Logo
2:40 pm - 8:43 pmSDQ-VPS
7h 03m1 stop
$516Delta
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Sun, Mar 29 - Wed, Apr 8
WestJet Logo
12:45 pm - 2:30 pmVPS-KIN
25h 45m2 stops
WestJet Logo
3:30 pm - 6:29 pmKIN-VPS
26h 59m2 stops
$3,340WestJet
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Tue, Dec 2 - Sun, Dec 7
WestJet Logo
5:00 pm - 1:35 pmVPS-PUJ
18h 35m2 stops
WestJet Logo
2:30 pm - 12:12 pmPUJ-VPS
23h 42m2 stops
$3,456WestJet
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Booking Insights

KAYAK's insights & trends for Valparaiso to Caribbean flights

Get data-powered insights and trends into flights from Valparaiso to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Valparaiso to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Valparaiso to Caribbean, 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 is January, when tickets cost $347 (return) on average. On the other hand, the most expensive months are February and August, when the average cost of round-trip tickets is $663 and $589 respectively.

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

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

If you are looking for a flight deal from Valparaiso to Caribbean, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Caribbean, Friday is the cheapest day to fly and Wednesday is the most expensive.

Good to know

Low seasonAugust
Cheapest flight$237
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Valparaiso to San Juan Airport

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Valparaiso to Caribbean?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Valparaiso to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Valparaiso to Caribbean 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?

    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 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?

    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 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?

    The cheapest time of day to fly to Caribbean 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 is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $503.

Reviews of the top 3 airlines serving from Valparaiso to Caribbean

 
Need help choosing which airline to fly with from Valparaiso to Caribbean? 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.
8.0
SouthwestOverall score based on 4241 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

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.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

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