$196 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 8/31. 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 72 hours
Punta Cana
Punta Cana1 stop$676
Santo Domingo
Santo Domingo1 stop$574
Montego Bay
Montego Bay1 stop$441
Oranjestad
Oranjestad2 stops$588
Nassau
Nassau2 stops$561
Kingston
Kingston1 stop$763
Simpson Bay
Simpson Bay1 stop$676
George Town
George Town1 stop$660
Willemstad
Willemstad2 stops$1,342
Punta Cana
Punta Cana1 stop$676
Santo Domingo
Santo Domingo1 stop$574
Montego Bay
Montego Bay1 stop$441
Oranjestad
Oranjestad2 stops$588
Nassau
Nassau2 stops$561
Kingston
Kingston1 stop$763
Simpson Bay
Simpson Bay1 stop$676
George Town
George Town1 stop$660
Willemstad
Willemstad2 stops$1,342

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, Oct 22 - Tue, Oct 27
Southwest Logo
2:00 pm - 12:20 am
VPS
-
SJU
9h 20m
2 stops
Southwest Logo
5:50 am - 1:30 pm
SJU
-
VPS
8h 40m
1 stop
$399Southwest
Sat, Sep 5 - Mon, Sep 14
Southwest Logo
12:15 pm - 9:55 pm
VPS
-
SJU
8h 40m
1 stop
Southwest Logo
6:00 am - 3:25 pm
SJU
-
VPS
10h 25m
2 stops
$407Southwest
Sat, Sep 19 - Sat, Oct 17
American Airlines Logo
5:40 am - 12:53 pm
VPS
-
MBJ
7h 13m
1 stop
American Airlines Logo
5:13 pm - 11:48 pm
MBJ
-
VPS
6h 35m
1 stop
$441American Airlines
Sat, Sep 19 - Sat, Oct 17
American Airlines Logo
4:29 pm - 12:53 pm
VPS
-
MBJ
20h 24m
2 stops
American Airlines Logo
5:13 pm - 11:48 pm
MBJ
-
VPS
6h 35m
1 stop
$445American Airlines
Thu, Oct 22 - Tue, Oct 27
Delta Logo
7:00 am - 4:33 pm
VPS
-
SJU
8h 33m
1 stop
Delta Logo
2:31 pm - 11:13 pm
SJU
-
VPS
9h 42m
1 stop
$497Delta
Mon, Jan 4 - Sat, Jan 9
Delta Logo
7:45 am - 4:45 pm
VPS
-
NAS
8h 00m
1 stop
Delta Logo
2:55 pm - 8:41 pm
NAS
-
VPS
6h 46m
1 stop
$575Delta
Mon, Aug 3 - Sat, Aug 8
JetBlue Logo
9:59 am - 1:12 am
VPS
-
SDQ
14h 13m
1 stop
JetBlue Logo
5:01 am - 3:04 pm
SDQ
-
VPS
11h 03m
1 stop
$966JetBlue
Mon, Aug 3 - Sat, Aug 8
JetBlue Logo
3:59 pm - 11:55 am
VPS
-
AUA
18h 56m
1 stop
JetBlue Logo
6:00 pm - 3:04 pm
AUA
-
VPS
22h 04m
1 stop
$1,089JetBlue
Mon, Jan 4 - Sat, Jan 9
WestJet Logo
2:25 pm - 3:40 pm
VPS
-
NAS
24h 15m
2 stops
WestJet Logo
4:50 pm - 6:28 pm
NAS
-
VPS
26h 38m
2 stops
$1,460WestJet
Thu, Jan 7 - Mon, Jan 11
WestJet Logo
9:25 am - 6:50 pm
VPS
-
AUA
31h 25m
2 stops
WestJet Logo
4:30 pm - 11:07 pm
AUA
-
VPS
32h 37m
2 stops
$3,535WestJet
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 $330, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$196
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 13% 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.
7.8
DeltaOverall score based on 8469 reviews
8.5Crew
7.8Entertainment
8.1Boarding
7.8Comfort
7.2Food
Airline reviews

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.

8.0 ExcellentRoseanne, Jul 2026
FLL - ATL
Read more Delta reviews

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.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

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