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Valparaiso

$258+ Cheap flights from Caribbean Islands to Valparaiso, FL (VPS)

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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — VPS
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Valparaiso

Keep the following information in mind while searching for Caribbean Islands to Valparaiso flight deals. Data was last updated January 12, 2026.

Round-trip from

$346
(Southwest)

One-way from

$258
(Delta)
From Caribbean Islands to Valparaiso Destin-Ft Walton Beach
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One-way flight from Caribbean Islands to Valparaiso Destin-Ft Walton Beach
Search Deals

Find flight deals from Caribbean Islands to Valparaiso

Cheapest flights from Caribbean Islands to Valparaiso
Explore the most affordable flight options available from Caribbean Islands to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This American Airlines deal was found by Cheapflights users on 1/11. 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.
Tue 8/181:35 pm
SJU
-
VPS
2 stops10h 15m
American Airlines
Sat 8/297:30 pm
VPS
-
SJU
1 stop17h 55m
American Airlines
Deal found 1/11$365
This Southwest deal was found by Cheapflights users on 1/10. 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 6/166:30 am
SJU
-
VPS
2 stops9h 50m
Southwest
Sun 6/217:25 am
VPS
-
SJU
1 stop9h 45m
Southwest
Deal found 1/10$375
This American Airlines deal was found by Cheapflights users on 1/11. 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.
Wed 3/2511:30 am
SJU
-
VPS
1 stop11h 54m
American Airlines
Sun 3/294:40 pm
VPS
-
SJU
2 stops15h 20m
American Airlines
Deal found 1/11$386
This Southwest deal was found by Cheapflights users on 1/10. 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 6/155:00 am
SJU
-
VPS
2 stops9h 20m
Southwest
Sun 6/217:25 am
VPS
-
SJU
1 stop9h 45m
Southwest
Deal found 1/10$395
This American Airlines deal was found by Cheapflights users on 1/11. 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 2/1312:46 pm
SJU
-
VPS
2 stops11h 38m
American Airlines
Sun 2/157:03 am
VPS
-
SJU
1 stop14h 28m
American Airlines
Deal found 1/11$405
This Southwest deal was found by Cheapflights users on 1/12. 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 1/306:10 am
SJU
-
VPS
2 stops14h 45m
Southwest
Thu 2/57:10 am
VPS
-
SJU
2 stops14h 55m
Southwest
Deal found 1/12$451
This Southwest deal was found by Cheapflights users on 1/10. 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.
Sat 1/175:30 am
SJU
-
VPS
2 stops13h 50m
Southwest
Fri 1/3012:15 pm
VPS
-
SJU
2 stops10h 20m
Southwest
Deal found 1/10$456
This Southwest deal was found by Cheapflights users on 1/11. 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 2/1310:50 am
SJU
-
VPS
2 stops12h 20m
Southwest
Sun 2/152:30 pm
VPS
-
SJU
2 stops8h 10m
Southwest
Deal found 1/11$476
This American Airlines deal was found by Cheapflights users on 1/12. 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 1/306:00 am
SJU
-
VPS
2 stops17h 00m
American Airlines
Thu 2/56:00 am
VPS
-
SJU
1 stop10h 22m
American Airlines
Deal found 1/12$505
This Delta deal was found by Cheapflights users on 1/10. 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 1/216:27 pm
SJU
-
VPS
1 stop6h 38m
Delta
Mon 2/26:00 am
VPS
-
SJU
1 stop9h 17m
Delta
Deal found 1/10$515
This American Airlines deal was found by Cheapflights users on 1/11. 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.
Wed 5/131:32 pm
STI
-
VPS
1 stop11h 18m
American Airlines
Fri 9/186:00 am
VPS
-
STI
1 stop5h 20m
American Airlines
Deal found 1/11$587

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Valparaiso 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 12, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Valparaiso that are best for you.

Fly from

Caribbean Islands

Fly to

Valparaiso

Route

Depart

Return

Price

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Wed 3/25

1:44 pm-10:24 pm

1 stop9h 40m

Valparaiso Destin-Ft Walton Beach

Sun 3/29

6:00 am-10:58 pm

1 stop15h 58m

$365

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Mon 6/15

6:00 am-5:20 pm

1 stop12h 20m

Valparaiso Destin-Ft Walton Beach

Sun 6/21

7:25 am-6:10 pm

1 stop9h 45m

$375

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Tue 6/16

6:30 am-3:20 pm

2 stops9h 50m

Valparaiso Destin-Ft Walton Beach

Sun 6/21

7:25 am-6:10 pm

1 stop9h 45m

$375

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Fri 2/13

2:44 pm-10:24 pm

1 stop9h 40m

Valparaiso Destin-Ft Walton Beach

Sun 2/15

6:00 am-9:34 pm

1 stop13h 34m

$405

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-6:55 pm

2 stops14h 45m

Valparaiso Destin-Ft Walton Beach

Thu 2/5

7:10 am-12:05 am

2 stops14h 55m

$451

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Fri 2/13

10:50 am-9:10 pm

2 stops12h 20m

Valparaiso Destin-Ft Walton Beach

Sun 2/15

2:30 pm-12:40 am

2 stops8h 10m

$476

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Fri 1/30

6:00 am-9:00 pm

2 stops17h 00m

Valparaiso Destin-Ft Walton Beach

Thu 2/5

6:00 am-6:22 pm

1 stop10h 22m

$505

Santiago de los CaballerosValparaiso

STI - VPS

STIVPS

Santiago de los Caballeros

Wed 5/13

1:32 pm-11:50 pm

1 stop11h 18m

Valparaiso Destin-Ft Walton Beach

Fri 9/18

6:00 am-12:20 pm

1 stop5h 20m

$587

Santiago de los CaballerosValparaiso

STI - VPS

STIVPS

Santiago de los Caballeros

Fri 5/15

1:32 pm-11:50 pm

1 stop11h 18m

Valparaiso Destin-Ft Walton Beach

Tue 9/15

6:00 am-12:20 pm

1 stop5h 20m

$587

San JuanValparaiso

SJU - VPS

SJUVPS

San Juan Luis Munoz Marin Intl

Sat 4/25

6:15 am-2:08 pm

1 stop8h 53m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 17 results
1
2

Best time to book a flight from Caribbean Islands to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Caribbean Islands 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 Caribbean Islands to Valparaiso

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

Currently, October is the cheapest month in which you can book a flight from Caribbean Islands to Valparaiso, Florida (average of $187). Flying from Caribbean Islands to Valparaiso, Florida in December is currently the most expensive (average of $375). 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 Valparaiso

Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated January 12, 2026.
Get a feel of what it's like to fly with American Airlines from Caribbean Islands to Valparaiso by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,111 reviews

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,111 reviews
American Airlines
7.2
Good
11,111 reviews

Overall

7.2

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Valparaiso. 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 into for flights to Valparaiso from Caribbean Islands?

    Located just 3.1 mi from the city center, Valparaiso Destin-Ft Walton Beach (VPS) is the airport most travelers will use when flying to Valparaiso from Caribbean Islands.

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

    There are many flights that can get you from Caribbean Islands to Valparaiso, Florida in 9h 40m. Fly via American Airlines or Southwest to get the fastest option. There are 1532 mi between Caribbean Islands and Valparaiso, Florida. This flight may include one or multiple stops.

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

    The most popular route from Caribbean Islands to Valparaiso, Florida is San Juan Luis Munoz Marin Intl - Valparaiso Destin-Ft Walton Beach. You may also consider Santo Domingo Las Americas - Valparaiso Destin-Ft Walton Beach or Vieques - Valparaiso Destin-Ft Walton Beach.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Valparaiso 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 Caribbean Islands to Valparaiso, Florida?

    Currently, October is the cheapest month in which you can book a flight from Caribbean Islands to Valparaiso, Florida (average of $187). Flying from Caribbean Islands to Valparaiso, Florida in December is currently the most expensive (average of $375). 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

Traveling to a place near Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Crestview
Andalusia
Niceville

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Alternative routes for Caribbean Islands to Valparaiso

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Caribbean Islands to Valparaiso

Discover the top 3 airlines that operate flights from Caribbean Islands to Valparaiso. 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 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$334Average$358FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$365Average$522FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$521Average$589FlexibilityNo cancel feeOn-time71%

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