$188 Find Cheap Flights from Valparaiso to Caribbean Islands - Compare and Save

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 9/21. 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 Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$855
Santo Domingo
Santo Domingo1 stop$549
Montego Bay
Montego Bay1 stop$665
Nassau
Nassau1 stop$594
Kingston
Kingston1 stop$758
Simpson Bay
Simpson Bay2 stops$660
George Town
George Town1 stop$635
Willemstad
Willemstad1 stop$647
St. John's
St. John's2 stops$3,632
Punta Cana
Punta Cana1 stop$855
Santo Domingo
Santo Domingo1 stop$549
Montego Bay
Montego Bay1 stop$665
Nassau
Nassau1 stop$594
Kingston
Kingston1 stop$758
Simpson Bay
Simpson Bay2 stops$660
George Town
George Town1 stop$635
Willemstad
Willemstad1 stop$647
St. John's
St. John's2 stops$3,632
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 $304, 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 April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $891 and $852 respectively.

Good to know

Low season

August

Cheapest flight

$188
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 11% 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.
7.8
DeltaOverall score based on 8502 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Pushing back flight and ultimately cancelling it after multiple changes and hours of delays. Comm were terrible as to what was going on and what options were available.

2.0 MediocreEugene, Aug 2026
Read more Delta reviews

Pushing back flight and ultimately cancelling it after multiple changes and hours of delays. Comm were terrible as to what was going on and what options were available.

Some of the passengers are coming on board with luggage so overstuffed and/or too large that have no business going into the overhead bins.

Boarding was quick and i made my connection early due to early arrival time

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

There was a 6 hours delay in our departure. And yet, no compensation was offered. A company should be responsible for such a delay.

My flight was delayed several hours, which is to be expected (American never fails to disappoint me!), but the parts that really bothered me are as follows: 1) I was unable to add myself to the standby list for another flight in the app, nor could the gate agents figure out how to help me do so (the app is difficult to work with and simply did not allow me to perform the action of adding myself to the list) 2) When I asked the gate agents to add me to the standby list, the agent said that he had added me, but I was not able to confirm that I was on the list in the app; as it turns out, I had NOT been added to the list after all. He had lied to me and/or failed to add me to the list. 3) I figured out I had not been added to the standby list when I spoke to the (rather rude, snippy, and dismissive) other gate agent, who finally did add me to the list after giving me some pretty unnecessary attitude. I understand that gate agents experience the worst of stressed travelers every day, so I appreciate that I was eventually able to make it onto the standby flight with their help. However, the app needs some SERIOUS attention!

Nice ! I am gold member at United Airlnes probably I will shift at American Airlines and JAL ! Thank you ! Kindly maintain quality service I fly often! ❤️

The flight was delayed 4 hours, and when we finally boarded, they told us that the fuel was only just then checked. So, we waited even longer to take off.

Everything was done like clockwork and I find no fault with the airline.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

This leg they tried and did well with what they had to work from.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports