$198 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 4/10. 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 Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$778
Montego Bay
Montego Bay2 stops$355
Oranjestad
Oranjestad1 stop$685
Nassau
Nassau1 stop$534
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$636
Willemstad
Willemstad2 stops$612
St. John's
St. John's1 stop$835
Punta Cana
Punta Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$778
Montego Bay
Montego Bay2 stops$355
Oranjestad
Oranjestad1 stop$685
Nassau
Nassau1 stop$534
Kingston
Kingston1 stop$713
Simpson Bay
Simpson Bay1 stop$636
Willemstad
Willemstad2 stops$612
St. John's
St. John's1 stop$835

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, Apr 30 - Mon, May 4
American Airlines Logo
4:46 pm - 3:37 pm
VPS
-
MBJ
22h 51m
2 stops
American Airlines Logo
4:37 pm - 11:52 am
MBJ
-
VPS
19h 15m
2 stops
$355American Airlines
Thu, Apr 30 - Mon, May 4
American Airlines Logo
7:43 am - 11:24 am
VPS
-
MBJ
27h 41m
1 stop
American Airlines Logo
2:29 pm - 9:35 pm
MBJ
-
VPS
7h 06m
1 stop
$357American Airlines
Mon, Apr 13 - Wed, May 6
Multiple Airlines Logo
8:00 am - 7:19 pm
VPS
-
SJU
10h 19m
1 stop
Multiple Airlines Logo
6:41 pm - 7:56 pm
SJU
-
VPS
26h 15m
2 stops
$386Multiple Airlines
Mon, Apr 13 - Sun, May 3
Multiple Airlines Logo
8:00 am - 7:19 pm
VPS
-
SJU
10h 19m
1 stop
Multiple Airlines Logo
3:21 am - 6:46 pm
SJU
-
VPS
16h 25m
2 stops
$388Multiple Airlines
Tue, Apr 28 - Sun, May 3
Southwest Logo
10:25 am - 10:40 pm
VPS
-
SJU
11h 15m
2 stops
Southwest Logo
5:35 am - 5:25 pm
SJU
-
VPS
12h 50m
2 stops
$406Southwest
Tue, Apr 28 - Sun, May 3
Southwest Logo
10:25 am - 11:40 pm
VPS
-
SJU
12h 15m
2 stops
Southwest Logo
5:00 am - 1:15 pm
SJU
-
VPS
9h 15m
1 stop
$420Southwest
Thu, Aug 20 - Wed, Aug 26
Delta Logo
7:45 am - 1:35 pm
VPS
-
NAS
4h 50m
1 stop
Delta Logo
3:00 pm - 11:08 pm
NAS
-
VPS
9h 08m
1 stop
$559Delta
Thu, Aug 20 - Sat, Aug 22
Delta Logo
6:00 am - 1:35 pm
VPS
-
NAS
6h 35m
1 stop
Delta Logo
3:00 pm - 11:08 pm
NAS
-
VPS
9h 08m
1 stop
$584Delta
Sat, Apr 18 - Wed, Apr 22
JetBlue Logo
9:59 am - 10:32 pm
VPS
-
STI
11h 33m
1 stop
JetBlue Logo
8:46 pm - 9:09 am
STI
-
VPS
13h 23m
1 stop
$730JetBlue
Mon, Jun 8 - Mon, Jun 15
JetBlue Logo
9:59 am - 1:00 am
VPS
-
STI
14h 01m
1 stop
JetBlue Logo
5:01 am - 3:00 pm
STI
-
VPS
10h 59m
1 stop
$735JetBlue
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 $324, 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 May, when tickets cost $374 (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$198
Most popular time to fly with an average 5% increase in price.
Flight from Valparaiso to Montego Bay

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 8293 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

10.0 ExcellentAnonymous, Mar 2026
TPA - ATL
Read more Delta reviews

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

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.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

Other than nearly three hour delay for maintenance issues, everything went smooth

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports