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Caribbean Islands

$232+ Cheap flights from Valparaiso, FL (VPS) to Caribbean Islands

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 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Valparaiso to Caribbean Islands

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

Round-trip from

$345
(Southwest)

One-way from

$232
(Delta)

Popular in

February

Cheapest in

September

Average price

$624
From Valparaiso Destin-Ft Walton Beach to Caribbean Islands
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One-way flight from Valparaiso Destin-Ft Walton Beach to Caribbean Islands
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Highest demand for flights based on searches. 13% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Valparaiso to Caribbean Islands

Cheapest flights from Valparaiso to Caribbean Islands
Explore the most affordable flight options available from Valparaiso to Caribbean Islands. 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 1/12. 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 8/147:07 am
VPS
-
SJU
1 stop14h 49m
American Airlines
Thu 8/207:05 pm
SJU
-
VPS
1 stop5h 53m
American Airlines
Deal found 1/12$373
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:35 pm
VPS
-
SJU
1 stop11h 55m
American Airlines
Mon 11/166:00 am
SJU
-
VPS
2 stops17h 10m
American Airlines
Deal found 1/10$385
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 10/147:43 am
VPS
-
SJU
2 stops9h 22m
American Airlines
Sat 10/2412:05 pm
SJU
-
VPS
2 stops9h 58m
American Airlines
Deal found 1/11$390
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.
Wed 1/217:00 am
VPS
-
SJU
2 stops10h 05m
Southwest
Tue 1/2710:20 am
SJU
-
VPS
2 stops10h 35m
Southwest
Deal found 1/11$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 2/206:00 am
VPS
-
SJU
1 stop15h 34m
American Airlines
Mon 2/237:01 pm
SJU
-
VPS
1 stop6h 58m
American Airlines
Deal found 1/11$405
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:25 pm
VPS
-
SJU
2 stops15h 44m
American Airlines
Sat 8/1512:00 pm
SJU
-
VPS
2 stops11h 50m
American Airlines
Deal found 1/10$410
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.
Fri 11/136:00 am
VPS
-
SJU
1 stop9h 25m
Delta
Mon 11/161:55 pm
SJU
-
VPS
1 stop11h 12m
Delta
Deal found 1/10$415
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.
Tue 2/34:06 pm
VPS
-
SJU
2 stops18h 24m
American Airlines
Tue 2/108:20 am
SJU
-
VPS
1 stop10h 10m
American Airlines
Deal found 1/12$425
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.
Thu 2/196:00 am
VPS
-
SJU
1 stop13h 34m
American Airlines
Tue 2/248:00 am
SJU
-
VPS
2 stops9h 52m
American Airlines
Deal found 1/12$435
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.
Mon 1/197:10 am
VPS
-
SJU
2 stops14h 55m
Southwest
Fri 1/305:40 am
SJU
-
VPS
2 stops15h 15m
Southwest
Deal found 1/11$455
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:40 am
VPS
-
SJU
1 stop30h 59m
Multiple Airlines
Sat 3/147:00 am
SJU
-
VPS
2 stops37h 53m
Multiple Airlines
Deal found 1/11$460
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.
Sat 7/186:39 pm
VPS
-
NAS
1 stop14h 23m
American Airlines
Fri 7/244:04 pm
NAS
-
VPS
1 stop8h 46m
American Airlines
Deal found 1/12$466

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Caribbean Islands 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 Valparaiso to Caribbean Islands that are best for you.

Fly from

Valparaiso

Fly to

Caribbean Islands

Route

Depart

Return

Price

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Thu 2/19

7:03 am-11:31 pm

1 stop14h 28m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:00 am-3:52 pm

2 stops10h 52m

$405

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 2/20

6:00 am-6:11 pm

1 stop10h 11m

San Juan Luis Munoz Marin Intl

Tue 2/24

8:00 am-3:52 pm

2 stops9h 52m

$405

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sun 6/21

7:25 am-6:10 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Sun 6/28

5:45 am-3:10 pm

1 stop10h 25m

$425

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Tue 2/3

5:00 pm-12:30 pm

2 stops17h 30m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-3:15 pm

2 stops11h 15m

$425

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Thu 2/26

7:42 am-4:20 pm

1 stop6h 38m

San Juan Luis Munoz Marin Intl

Mon 3/2

10:50 am-10:24 pm

2 stops13h 34m

$435

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Wed 5/6

6:00 am-1:46 pm

1 stop6h 46m

Nassau Intl

Sat 5/9

5:08 pm-11:08 pm

1 stop7h 00m

$471

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Sun 4/19

6:20 am-2:35 pm

1 stop7h 15m

Punta Cana

Thu 4/23

2:35 pm-11:50 pm

1 stop10h 15m

$473

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Wed 5/6

6:20 am-10:59 am

1 stop3h 39m

Nassau Intl

Sat 5/9

12:00 pm-9:39 pm

2 stops10h 39m

$476

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Wed 4/1

7:00 am-3:43 pm

1 stop7h 43m

Punta Cana

Mon 4/6

4:36 pm-4:06 pm

1 stop24h 30m

$534

ValparaisoMontego Bay

VPS - MBJ

VPSMBJ

Valparaiso Destin-Ft Walton Beach

Sat 3/7

4:40 pm-12:27 pm

2 stops18h 47m

Montego Bay Sangster Intl

Thu 3/12

10:07 am-11:59 pm

1 stop13h 52m

$535

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 46 results
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Best time to book a flight from Valparaiso to Caribbean Islands

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

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

Currently, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean Islands (average of $98). Flying from Valparaiso, Florida to Caribbean Islands 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated January 12, 2026.
See what other customers who have flown with Delta and American Airlines from Valparaiso to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,039 reviews

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
8,039 reviews
Delta
7.9
Good
8,039 reviews

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
11,114 reviews
Delta
7.9
Good
8,039 reviews

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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 Islands. 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 Islands?

    If you book a flight to Caribbean Islands from Valparaiso, you will be flying from Destin-Ft Walton Beach, which is the city’s only airport. Valparaiso Destin-Ft Walton Beach (VPS) is located 3.1 mi from the center of Valparaiso.

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

    Airlines like Southwest, American Airlines, and Delta fly from Valparaiso, Florida to Caribbean Islands in about 6h 46m. The time it takes to get you to your destination can typically vary by up to 5h 09m. The distance between Valparaiso, Florida and Caribbean Islands is about 670 mi. 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 Islands?

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

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean Islands (average of $98). Flying from Valparaiso, Florida to Caribbean Islands 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

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Top 3 airlines flying from Valparaiso to Caribbean Islands

Discover the top 3 airlines that operate flights from Valparaiso to Caribbean Islands. 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
SouthwestCheapest$334Average$478FlexibilityNo cancel feeOn-time63%
DeltaCheapest$334Average$602FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$526FlexibilityNo cancel feeOn-time71%

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