$247 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 4/28. 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$528
Santo Domingo
Santo Domingo1 stop$457
Montego Bay
Montego Bay2 stops$482
Oranjestad
Oranjestad1 stop$595
Nassau
Nassau1 stop$476
Simpson Bay
Simpson Bay1 stop$601
George Town
George Town1 stop$987
Willemstad
Willemstad1 stop$537
Punta Cana
Punta Cana1 stop$528
Santo Domingo
Santo Domingo1 stop$457
Montego Bay
Montego Bay2 stops$482
Oranjestad
Oranjestad1 stop$595
Nassau
Nassau1 stop$476
Simpson Bay
Simpson Bay1 stop$601
George Town
George Town1 stop$987
Willemstad
Willemstad1 stop$537

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 - Mon, May 11
Southwest Logo
2:00 pm - 11:40 pm
VPS
-
SJU
8h 40m
1 stop
Southwest Logo
6:50 am - 5:15 pm
SJU
-
VPS
11h 25m
2 stops
$375Southwest
Fri, Apr 10 - Mon, Apr 13
American Airlines Logo
6:20 am - 9:24 pm
VPS
-
SJU
14h 04m
1 stop
American Airlines Logo
10:03 am - 11:50 pm
SJU
-
VPS
14h 47m
1 stop
$390American Airlines
Mon, Mar 9 - Tue, Mar 17
Southwest Logo
7:20 am - 10:55 pm
VPS
-
SJU
14h 35m
2 stops
Southwest Logo
5:15 am - 1:15 pm
SJU
-
VPS
9h 00m
1 stop
$391Southwest
Fri, Apr 10 - Mon, Apr 13
American Airlines Logo
6:20 am - 6:10 pm
VPS
-
SJU
10h 50m
1 stop
American Airlines Logo
10:03 am - 11:50 pm
SJU
-
VPS
14h 47m
1 stop
$395American Airlines
Sat, May 16 - Tue, May 19
Southwest Logo
12:10 pm - 11:15 pm
VPS
-
SJU
10h 05m
1 stop
Southwest Logo
5:05 am - 1:10 pm
SJU
-
VPS
9h 05m
1 stop
$410Southwest
Mon, Mar 16 - Tue, Mar 24
Delta Logo
6:00 am - 2:45 pm
VPS
-
STT
7h 45m
1 stop
Delta Logo
1:55 pm - 11:15 pm
STT
-
VPS
10h 20m
1 stop
$569Delta
Tue, May 19 - Sun, May 24
Delta Logo
7:00 am - 1:24 pm
VPS
-
PUJ
5h 24m
1 stop
Delta Logo
4:05 pm - 10:53 pm
PUJ
-
VPS
7h 48m
1 stop
$595Delta
Thu, Mar 12 - Thu, Mar 19
JetBlue Logo
9:59 am - 3:16 pm
VPS
-
NAS
28h 17m
1 stop
JetBlue Logo
11:55 am - 2:59 pm
NAS
-
VPS
28h 04m
1 stop
$661JetBlue
Mon, Mar 30 - Mon, Apr 6
WestJet Logo
6:00 am - 8:57 am
VPS
-
PUJ
25h 57m
2 stops
WestJet Logo
3:30 pm - 6:39 pm
PUJ
-
VPS
28h 09m
2 stops
$2,200WestJet
Mon, Apr 27 - Wed, Apr 29
WestJet Logo
6:00 am - 2:15 pm
VPS
-
AUA
31h 15m
2 stops
WestJet Logo
3:05 pm - 6:40 pm
AUA
-
VPS
28h 35m
2 stops
$3,359WestJet
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 $319, 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 September, when tickets cost $384 (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$247
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 12% 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 8205 reviews
8.1Boarding
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
Airline reviews

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

10.0 ExcellentSharon, Feb 2026
TPA - ATL
Read more Delta reviews

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

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports