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Caribbean Islands

$281+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
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 November 25, 2025.

Round-trip from

$344
(Southwest)

One-way from

$281
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$648
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. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 25, 2025.

This Southwest deal was found by Cheapflights users on 11/24. 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 12/2411:20 amVPS - SJU
2 stops11h 15mSouthwest
Wed 12/316:40 amSJU - VPS
2 stops16h 30mSouthwest
Deal found 11/24$504
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/246:50 amVPS - SJU
1 stop14h 37mAmerican Airlines
Wed 12/316:57 pmSJU - VPS
1 stop7h 01mAmerican Airlines
Deal found 11/24$514
This Delta deal was found by Cheapflights users on 11/24. 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 12/82:14 pmVPS - SJU
1 stop7h 06mDelta
Thu 12/117:00 amSJU - VPS
1 stop11h 07mDelta
Deal found 11/24$524
This American Airlines deal was found by Cheapflights users on 11/25. 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 12/44:40 pmVPS - SJU
2 stops17h 19mAmerican Airlines
Sun 12/147:00 amSJU - VPS
1 stop13h 48mAmerican Airlines
Deal found 11/25$544
This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/96:00 amVPS - SJU
1 stop9h 28mDelta
Sat 12/137:00 amSJU - VPS
1 stop8h 29mDelta
Deal found 11/24$549
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/256:00 amVPS - SJU
1 stop7h 48mAmerican Airlines
Wed 12/316:57 pmSJU - VPS
1 stop7h 01mAmerican Airlines
Deal found 11/24$624
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Wed 12/2412:53 pmVPS - KIN
2 stops27h 16mAmerican Airlines
Tue 1/131:39 pmKIN - VPS
2 stops21h 40mAmerican Airlines
Deal found 11/25$646
This Delta deal was found by Cheapflights users on 11/24. 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.
Sun 12/217:15 amVPS - MBJ
1 stop12h 26mDelta
Mon 1/58:00 amMBJ - VPS
1 stop9h 05mDelta
Deal found 11/24$654
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/237:39 amVPS - SJU
2 stops14h 00mAmerican Airlines
Wed 12/316:57 pmSJU - VPS
1 stop7h 01mAmerican Airlines
Deal found 11/24$694
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Wed 12/2412:53 pmVPS - KIN
2 stops27h 16mAmerican Airlines
Thu 1/16:25 amKIN - VPS
2 stops16h 07mAmerican Airlines
Deal found 11/25$696
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/187:39 amVPS - MBJ
1 stop5h 35mAmerican Airlines
Mon 12/222:23 pmMBJ - VPS
1 stop10h 35mAmerican Airlines
Deal found 11/24$699
This Delta deal was found by Cheapflights users on 11/24. 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 12/196:00 amVPS - MBJ
1 stop6h 04mDelta
Sun 12/288:00 amMBJ - VPS
1 stop8h 55mDelta
Deal found 11/24$713

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 November 25, 2025.
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

Sun 1/25

2:30 pm-12:40 am

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Thu 1/29

5:40 am-6:55 pm

2 stops15h 15m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sun 1/25

9:23 am-5:17 pm

1 stop5h 54m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-11:15 am

1 stop5h 45m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 2/20

6:00 am-11:32 pm

1 stop15h 32m

San Juan Luis Munoz Marin Intl

Tue 2/24

8:15 am-3:59 pm

2 stops9h 44m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sun 1/25

8:30 am-5:03 pm

1 stop6h 33m

San Juan Luis Munoz Marin Intl

Thu 1/29

11:38 am-9:00 pm

2 stops11h 22m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sat 2/21

4:35 pm-11:41 am

1 stop17h 06m

San Juan Luis Munoz Marin Intl

Wed 2/25

2:26 pm-10:19 pm

2 stops9h 53m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Thu 2/19

7:40 am-11:32 pm

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:00 am-3:12 pm

2 stops10h 12m

$384

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Mon 2/23

6:00 am-1:33 pm

1 stop6h 33m

Nassau Intl

Thu 2/26

6:27 pm-11:03 pm

1 stop5h 36m

$445

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Mon 2/23

6:00 am-4:22 pm

1 stop8h 22m

Saint Thomas Island Cyril E King

Thu 2/26

1:52 pm-8:19 pm

1 stop8h 27m

$478

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Thu 2/5

6:00 am-5:55 pm

1 stop10h 55m

Nassau Intl

Mon 2/9

6:45 pm-10:59 pm

1 stop5h 14m

$523

ValparaisoMontego Bay

VPS - MBJ

VPSMBJ

Valparaiso Destin-Ft Walton Beach

Sun 2/22

7:06 pm-11:13 am

1 stop15h 07m

Montego Bay Sangster Intl

Thu 2/26

4:44 pm-11:03 pm

1 stop7h 19m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 38 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, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean Islands (average of $112). 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.

What is the cheapest time of day to fly from VPS to EPX?

Find hourly flight availability from Valparaiso to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 25, 2025.

A simple way to save on the total cost of your ticket is to fly from Valparaiso, Florida to Caribbean Islands in the evening. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.

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 November 25, 2025.
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
7,999 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
7,999 reviews
Delta
7.9
Good
7,999 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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
11,038 reviews
Delta
7.9
Good
7,999 reviews

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.3

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, Delta, and American Airlines fly from Valparaiso, Florida to Caribbean Islands in about 5h 54m. The time it takes to get you to your destination can typically vary by up to 9h 38m. The distance between Valparaiso, Florida and Caribbean Islands is about 1532 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Caribbean Islands one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $281. However, be on the lookout for offers from Delta and Sun Country Air, as they are both options that can get you from Valparaiso, Florida to Caribbean Islands for a low price.

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

    While some choose either Valparaiso Destin-Ft Walton Beach - San Juan Luis Munoz Marin Intl or Valparaiso Destin-Ft Walton Beach - Kingston Norman Manley, Valparaiso Destin-Ft Walton Beach - Punta Cana 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, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean Islands (average of $112). 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.

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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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$615FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$334Average$478FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$334Average$542FlexibilityNo cancel feeOn-time71%

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