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$237+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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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 octubre 29, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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.
lun. 11/177:15 amVPS - SJU
2 stops9h 20mSouthwest
jue. 12/411:20 amSJU - VPS
2 stops11h 50mSouthwest
Deal found 10/27$344
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:30 amVPS - SJU
1 stop11h 39mAmerican Airlines
lun. 12/88:20 amSJU - VPS
1 stop9h 27mAmerican Airlines
Deal found 10/26$413
This American Airlines deal was found by Cheapflights users on 10/27. 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.
lun. 11/176:34 amVPS - SJU
1 stop13h 01mAmerican Airlines
vie. 12/511:00 amSJU - VPS
2 stops12h 04mAmerican Airlines
Deal found 10/27$424
This Southwest deal was found by Cheapflights users on 10/26. 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.
vie. 12/511:20 amVPS - SJU
2 stops11h 15mSouthwest
lun. 12/811:20 amSJU - VPS
2 stops11h 50mSouthwest
Deal found 10/26$444
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 11/204:40 pmVPS - SJU
2 stops15h 30mAmerican Airlines
dom. 12/76:00 amSJU - VPS
2 stops17h 24mAmerican Airlines
Deal found 10/27$454
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/206:35 amVPS - SJU
3 stops26h 14mMultiple Airlines
sáb. 12/64:10 amSJU - VPS
2 stops17h 46mMultiple Airlines
Deal found 10/27$467
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 12/47:35 amVPS - SJU
2 stops14h 18mAmerican Airlines
dom. 12/148:18 amSJU - VPS
1 stop9h 30mAmerican Airlines
Deal found 10/27$514
This Southwest deal was found by Cheapflights users on 10/27. 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.
vie. 10/3112:00 pmVPS - SJU
1 stop8h 35mSouthwest
dom. 11/25:40 amSJU - VPS
2 stops13h 40mSouthwest
Deal found 10/27$523
This American Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 12/64:40 pmVPS - PUJ
1 stop17h 01mAmerican Airlines
jue. 12/1112:51 pmPUJ - VPS
1 stop10h 33mAmerican Airlines
Deal found 10/27$526
This Southwest deal was found by Cheapflights users on 10/28. 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.
mié. 10/2912:05 pmVPS - SJU
1 stop9h 40mSouthwest
lun. 11/311:20 amSJU - VPS
2 stops11h 50mSouthwest
Deal found 10/28$532
This American Airlines deal was found by Cheapflights users on 10/29. 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.
dom. 12/77:35 amVPS - PUJ
1 stop7h 06mAmerican Airlines
dom. 12/1412:51 pmPUJ - VPS
1 stop10h 33mAmerican Airlines
Deal found 10/29$556
This American Airlines deal was found by Cheapflights users on 10/29. 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.
mié. 12/34:57 pmVPS - PUJ
2 stops16h 58mAmerican Airlines
dom. 12/75:41 pmPUJ - VPS
2 stops19h 01mAmerican Airlines
Deal found 10/29$619

Cheap flight deals from Valparaiso to Caribbean

Keep the following information in mind while searching for Valparaiso to Caribbean flight deals. Data was last updated octubre 29, 2025.

Round-trip from

$344
(Southwest)

One-way from

$237
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$424
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. 1% potential increase in price ($9 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 October 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 octubre 29, 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

lun. 11/17

7:15 am-6:35 pm

2 stops9h 20m

San Juan Luis Munoz Marin Intl

vie. 12/5

6:40 am-9:10 pm

2 stops16h 30m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

mar. 11/18

7:15 am-9:30 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

jue. 12/4

11:20 am-9:10 pm

2 stops11h 50m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

lun. 11/17

7:15 am-6:35 pm

2 stops9h 20m

San Juan Luis Munoz Marin Intl

jue. 12/4

11:20 am-9:10 pm

2 stops11h 50m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

jue. 2/19

7:40 am-11:27 pm

2 stops13h 47m

San Juan Luis Munoz Marin Intl

mar. 2/24

2:31 pm-10:22 pm

2 stops9h 51m

$384

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

vie. 12/5

8:30 am-10:09 pm

1 stop11h 39m

San Juan Luis Munoz Marin Intl

lun. 12/8

8:20 am-3:47 pm

1 stop9h 27m

$413

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

vie. 2/20

7:40 am-9:26 pm

1 stop11h 46m

San Juan Luis Munoz Marin Intl

mar. 2/24

8:19 am-6:51 pm

2 stops12h 32m

$414

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

lun. 3/16

5:04 pm-11:10 am

2 stops17h 06m

Nassau Intl

vie. 3/20

7:43 am-9:08 pm

2 stops14h 25m

$450

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

vie. 3/13

6:00 am-7:45 pm

1 stop12h 45m

Nassau Intl

mar. 3/17

12:50 pm-9:08 pm

1 stop9h 18m

$470

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

sáb. 3/14

5:04 pm-12:40 pm

2 stops18h 36m

Punta Cana

vie. 3/20

5:05 pm-10:37 am

2 stops18h 32m

$504

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

dom. 3/8

7:26 pm-2:35 pm

2 stops18h 09m

Santo Domingo Las Americas

sáb. 3/21

5:20 pm-10:37 am

2 stops18h 17m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 45 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, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $112). 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 octubre 29, 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 octubre 29, 2025.
See what other customers who have flown with Southwest, 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.
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 cheapest airlines to fly from Valparaiso, Florida to Caribbean one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $237. Delta flights start at $281 while deals on Sun Country Air start at $410 one-way.

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

    While some choose either Valparaiso Destin-Ft Walton Beach - Montego Bay Sangster Intl or Valparaiso Destin-Ft Walton Beach - Santo Domingo Las Americas, 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, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $112). 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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Top 3 airlines flying from Valparaiso to Caribbean

Discover the top 3 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$615FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$334Average$478FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$334Average$554FlexibilityNo cancel feeOn-time71%

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