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$272+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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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 December 12, 2025.

This Southwest deal was found by Cheapflights users on 12/10. 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.
Sun 12/212:00 pmVPS - SJU
2 stops9h 40mSouthwest
Tue 12/2311:35 amSJU - VPS
2 stops11h 35mSouthwest
Deal found 12/10$474
This Southwest deal was found by Cheapflights users on 12/10. 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.
Wed 12/2411:20 amVPS - SJU
2 stops11h 15mSouthwest
Wed 12/316:40 amSJU - VPS
2 stops16h 30mSouthwest
Deal found 12/10$504
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/246:00 amVPS - SJU
1 stop5h 41mAmerican Airlines
Wed 12/318:25 amSJU - VPS
1 stop9h 28mAmerican Airlines
Deal found 12/10$534
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sun 12/147:10 amVPS - SJU
2 stops13h 10mSouthwest
Tue 12/1611:20 amSJU - VPS
2 stops11h 50mSouthwest
Deal found 12/10$542
This Delta deal was found by Cheapflights users on 12/10. 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.
Sun 12/2112:00 pmVPS - SJU
1 stop9h 20mDelta
Wed 12/246:30 amSJU - VPS
1 stop9h 33mDelta
Deal found 12/10$554
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:58 pmVPS - SJU
2 stops21h 15mMultiple Airlines
Wed 12/248:40 amSJU - VPS
1 stop32h 15mMultiple Airlines
Deal found 12/10$560
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:00 amVPS - SJU
2 stops23h 58mMultiple Airlines
Wed 12/248:40 amSJU - VPS
1 stop32h 15mMultiple Airlines
Deal found 12/10$613
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:45 pmVPS - SJU
2 stops21h 16mMultiple Airlines
Mon 12/228:08 pmSJU - VPS
1 stop24h 15mMultiple Airlines
Deal found 12/10$621
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/256:00 amVPS - SJU
1 stop7h 48mAmerican Airlines
Mon 12/297:00 amSJU - VPS
1 stop18h 17mAmerican Airlines
Deal found 12/10$634
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/147:20 pmVPS - SJU
1 stop7h 59mAmerican Airlines
Tue 12/167:00 amSJU - VPS
1 stop9h 52mAmerican Airlines
Deal found 12/10$644
This Delta deal was found by Cheapflights users on 12/10. 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 12/2412:00 pmVPS - MBJ
1 stop7h 41mDelta
Sun 12/288:00 amMBJ - VPS
1 stop13h 37mDelta
Deal found 12/10$706
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/243:46 pmVPS - MBJ
2 stops20h 37mAmerican Airlines
Sun 12/284:24 pmMBJ - VPS
1 stop8h 34mAmerican Airlines
Deal found 12/10$765

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 December 12, 2025.

Round-trip from

$344
(Southwest)

One-way from

$272
(Delta)

Popular in

February

Cheapest in

January

Average price

$450
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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 2025.
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

Mon 1/26

7:00 am-8:55 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:40 am-6:55 pm

2 stops15h 15m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sat 3/14

4:40 pm-10:40 am

1 stop17h 00m

San Juan Luis Munoz Marin Intl

Wed 3/18

7:40 am-3:52 pm

1 stop9h 12m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Mon 1/26

8:30 am-11:59 pm

2 stops13h 29m

San Juan Luis Munoz Marin Intl

Wed 2/4

8:20 am-9:00 pm

1 stop14h 40m

$384

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Wed 2/25

7:59 am-7:06 pm

2 stops9h 07m

San Juan Luis Munoz Marin Intl

Mon 3/2

2:47 pm-10:20 pm

1 stop9h 33m

$384

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 2/20

4:36 pm-11:41 am

1 stop17h 05m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:00 am-3:59 pm

2 stops10h 59m

$389

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Wed 1/21

4:06 pm-12:30 pm

2 stops18h 24m

San Juan Luis Munoz Marin Intl

Sun 1/25

7:07 am-9:33 pm

1 stop16h 26m

$404

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 1/30

8:30 am-8:50 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

3:49 pm-9:00 pm

1 stop7h 11m

$414

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Mon 3/9

7:42 am-2:51 pm

1 stop6h 09m

Saint Thomas Island Cyril E King

Sun 3/15

1:52 pm-11:59 pm

1 stop11h 07m

$478

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Sat 3/7

3:52 pm-1:02 pm

2 stops19h 10m

Saint Thomas Island Cyril E King

Fri 3/13

3:40 pm-11:59 pm

1 stop9h 19m

$478

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Sun 3/8

4:40 pm-1:02 pm

2 stops19h 22m

Saint Thomas Island Cyril E King

Fri 3/13

1:52 pm-11:59 pm

1 stop11h 07m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 35 results
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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, January is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $115). 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.

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

Find hourly flight availability from Valparaiso to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Valparaiso, Florida to Caribbean in the evening. Doing so could potentially save you 34% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 December 12, 2025.
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
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

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
11,050 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

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. 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 15m. There are 1345 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 - San Juan Luis Munoz Marin Intl or Valparaiso Destin-Ft Walton Beach - Kingston Norman Manley, Valparaiso Destin-Ft Walton Beach - Saint Thomas Island Cyril E King 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, January is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $115). 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

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Alternative routes for Valparaiso to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$332Average$615FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$509FlexibilityNo cancel feeOn-time71%

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