HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$242+ Cheap flights from Valparaiso, FL (VPS) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Valparaiso to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Valparaiso to Caribbean

Cheapest flights from Valparaiso to Caribbean
Explore the most affordable flight options available from Valparaiso to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:00 pm
VPS
-
SJU
1 stop7h 40m
Southwest
Tue 4/2111:25 am
SJU
-
VPS
2 stops10h 35m
Southwest
Deal found 1/26$365
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:30 pm
VPS
-
SJU
2 stops8h 10m
Southwest
Fri 2/2710:50 am
SJU
-
VPS
2 stops12h 20m
Southwest
Deal found 1/25$370
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:20 am
VPS
-
SJU
1 stop14h 04m
American Airlines
Mon 4/136:56 pm
SJU
-
VPS
1 stop5h 54m
American Airlines
Deal found 1/25$385
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:00 pm
VPS
-
SJU
2 stops11h 35m
Southwest
Thu 2/2610:50 am
SJU
-
VPS
2 stops12h 20m
Southwest
Deal found 1/25$401
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:25 am
VPS
-
SJU
2 stops12h 10m
Southwest
Mon 3/97:00 am
SJU
-
VPS
2 stops9h 20m
Southwest
Deal found 1/25$406
This Southwest deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/152:00 pm
VPS
-
SJU
1 stop9h 15m
Southwest
Mon 6/295:30 am
SJU
-
VPS
1 stop8h 50m
Southwest
Deal found 1/26$420
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
VPS
-
SJU
1 stop9h 27m
Delta
Fri 2/276:42 pm
SJU
-
VPS
1 stop6h 21m
Delta
Deal found 1/25$425
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:20 am
VPS
-
SJU
1 stop5h 09m
American Airlines
Sat 5/237:09 pm
SJU
-
VPS
1 stop5h 41m
American Airlines
Deal found 1/25$435
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:03 am
VPS
-
SJU
1 stop14h 28m
American Airlines
Tue 2/2412:46 pm
SJU
-
VPS
2 stops11h 29m
American Airlines
Deal found 1/25$445
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
VPS
-
SJU
1 stop7h 49m
American Airlines
Sat 2/2810:50 am
SJU
-
VPS
1 stop15h 09m
American Airlines
Deal found 1/25$450
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:45 am
VPS
-
NAS
1 stop7h 09m
Delta
Fri 7/245:20 pm
NAS
-
VPS
1 stop4h 23m
Delta
Deal found 1/26$491
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:19 am
VPS
-
NAS
1 stop6h 14m
Delta
Fri 5/85:08 pm
NAS
-
VPS
1 stop7h 00m
Delta
Deal found 1/26$494

Find flight deals from Valparaiso to Caribbean

Keep the following information in mind while searching for Valparaiso to Caribbean flight deals. Data was last updated January 27, 2026.

Round-trip from

$365
(Southwest)

One-way from

$242
(Delta)

Popular in

February

Cheapest in

September

Average price

$584
From Valparaiso Destin-Ft Walton Beach to Caribbean
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Valparaiso to Caribbean that are best for you.

Fly from

Valparaiso

Fly to

Caribbean

Route

Depart

Return

Price

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Tue 4/14

2:00 pm-10:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 4/21

11:25 am-9:00 pm

2 stops10h 35m

$365

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Mon 2/23

2:30 pm-12:40 am

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Fri 2/27

10:50 am-9:10 pm

2 stops12h 20m

$370

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Mon 2/23

11:15 am-12:40 am

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Sat 2/28

7:35 am-8:55 pm

2 stops15h 20m

$401

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Thu 3/5

10:25 am-12:35 am

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Mon 3/9

7:00 am-3:20 pm

2 stops9h 20m

$406

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 4/10

4:46 pm-9:11 am

2 stops15h 25m

San Juan Luis Munoz Marin Intl

Mon 4/13

6:56 pm-11:50 pm

1 stop5h 54m

$410

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Mon 6/15

2:00 pm-12:15 am

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Mon 6/29

5:30 am-1:20 pm

1 stop8h 50m

$420

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Mon 2/23

6:00 am-5:27 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:42 pm-11:03 pm

1 stop6h 21m

$425

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Tue 3/17

7:59 am-3:40 pm

1 stop6h 41m

Saint Thomas Island Cyril E King

Mon 3/23

1:53 pm-11:59 pm

1 stop11h 06m

$499

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Fri 3/20

6:00 am-4:29 pm

1 stop9h 29m

Saint Thomas Island Cyril E King

Wed 3/25

4:42 pm-10:24 pm

1 stop6h 42m

$499

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

Thu 6/11

6:00 am-6:38 pm

1 stop11h 38m

Santo Domingo Las Americas

Sat 6/20

4:26 pm-11:50 pm

1 stop8h 24m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 36 results
1
2
3
4

Best time to book a flight from Valparaiso to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Valparaiso with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Valparaiso to Caribbean

What is the cheapest month to book a flight from Valparaiso, Florida to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $105). Flying from Valparaiso, Florida to Caribbean in September is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 27, 2026.
See what other customers who have flown with Delta and American Airlines from Valparaiso to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,119 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,119 reviews
Delta
7.9
Good
8,119 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,197 reviews
Delta
7.9
Good
8,119 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Valparaiso to Caribbean?

    For a flight from Valparaiso to Caribbean, you will be flying from Destin-Ft Walton Beach. Valparaiso Destin-Ft Walton Beach (VPS) is just 3.1 mi from the center of the city.

  • How long is the flight from Valparaiso, Florida to Caribbean?

    Departing from Valparaiso, Florida to Caribbean will take you 6h 41m. There are 1590 mi between Valparaiso, Florida and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Valparaiso, Florida to Caribbean?

    While some choose either Valparaiso Destin-Ft Walton Beach - Nassau Intl or Valparaiso Destin-Ft Walton Beach - Saint Thomas Island Cyril E King, Valparaiso Destin-Ft Walton Beach - San Juan Luis Munoz Marin Intl is the most popular route from Valparaiso, Florida to Caribbean.

  • Can I find deals for flights from Valparaiso to Caribbean that include hotel bookings?

    Yes. In addition to deals on Valparaiso to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Valparaiso to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Valparaiso to Caribbean.

  • Can I find deals for business class flights from Valparaiso to Caribbean?

    Yes. Cheapflights offers flight deals from Valparaiso to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Valparaiso, Florida to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $105). Flying from Valparaiso, Florida to Caribbean in September is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Valparaiso to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Miami to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to LaGuardia flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
Orlando to John F Kennedy Intl flights
Orlando to Las Vegas flights
Tampa to LaGuardia flights
Tampa to Newark flights
Tampa to John F Kennedy Intl flights
Orlando to LaGuardia flights
Orlando to Newark flights
Orlando to Los Angeles flights
Fort Lauderdale to Las Vegas flights
Miami to Madrid flights
Orlando to Seattle flights
West Palm Beach to Newark flights
Miami to Cancún flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Dulles Intl flights
Orlando to Denver flights
Tampa to Seattle flights
Miami to Denver flights
Miami to Mexico City flights
Tampa to Las Vegas flights
Orlando to Cancún flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Miami to Atlanta flights
Tampa to Denver flights
Fort Lauderdale to Atlanta flights
Orlando to Luis Munoz Marin Intl flights
Miami to Las Vegas flights
Tampa to Cancún flights
Miami to Heathrow flights
Miami to Leonardo da Vinci/Fiumicino flights
West Palm Beach to LaGuardia flights
Fort Lauderdale to Denver flights
Miami to Los Angeles flights
Miami to Jose Maria Cordova Intl flights
Fort Lauderdale to Detroit flights
Miami to Charles de Gaulle flights
Orlando to Heathrow flights
Miami to Dulles Intl flights
Tampa to Luis Munoz Marin Intl flights
Tampa to Atlanta flights
Orlando to Reagan-National flights
Jacksonville to John F Kennedy Intl flights
Miami to Ministro Pistarini flights
Miami to Barcelona-El Prat flights

Top 2 airlines flying from Valparaiso to Caribbean

Discover the top 2 airlines that operate flights from Valparaiso to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$299Average$602FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$356Average$529FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.