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Caribbean Islands

$171+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
nov. 5 — nov. 121
mié. 11/5
mié. 11/12
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 octubre 6, 2025.

Round-trip from

$344
(Southwest)

One-way from

$171
(Southwest)

Popular in

February

Cheapest in

January

Average price

$389
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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 6, 2025.

This Southwest deal was found by Cheapflights users on 10/5. 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. 11/37:15 amVPS - SJU
2 stops12h 15mSouthwest
lun. 11/1011:55 amSJU - VPS
2 stops11h 20mSouthwest
Deal found 10/5$364
This eDestinos deal was found by Cheapflights users on 10/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/186:30 amVPS - SJU
1 stop18h 32mMultiple Airlines
mié. 10/224:51 pmSJU - VPS
1 stop20h 59mMultiple Airlines
Deal found 10/5$392
This Southwest deal was found by Cheapflights users on 10/5. 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.
dom. 11/210:40 amVPS - SJU
2 stops12h 45mSouthwest
sáb. 11/88:20 amSJU - VPS
2 stops11h 35mSouthwest
Deal found 10/5$399
This American Airlines deal was found by Cheapflights users on 10/5. 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. 11/34:57 pmVPS - SJU
2 stops15h 20mAmerican Airlines
lun. 11/108:20 amSJU - VPS
1 stop9h 25mAmerican Airlines
Deal found 10/5$404
This American Airlines deal was found by Cheapflights users on 10/5. 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. 11/124:57 pmVPS - SJU
2 stops15h 20mAmerican Airlines
lun. 11/176:00 amSJU - VPS
2 stops16h 21mAmerican Airlines
Deal found 10/5$411
This American Airlines deal was found by Cheapflights users on 10/4. 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. 11/74:57 pmVPS - SJU
2 stops17h 08mAmerican Airlines
lun. 11/106:00 amSJU - VPS
2 stops16h 21mAmerican Airlines
Deal found 10/4$429
This Southwest deal was found by Cheapflights users on 10/5. 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.
sáb. 10/187:20 amVPS - SJU
2 stops10h 20mSouthwest
mié. 10/227:40 amSJU - VPS
2 stops10h 40mSouthwest
Deal found 10/5$479
This American Airlines deal was found by Cheapflights users on 10/5. 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. 11/167:20 pmVPS - SDQ
2 stops16h 45mAmerican Airlines
dom. 11/236:14 pmSDQ - VPS
2 stops19h 47mAmerican Airlines
Deal found 10/5$486
This American Airlines deal was found by Cheapflights users on 10/5. 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. 11/14:09 pmVPS - NAS
2 stops17h 34mAmerican Airlines
mar. 11/46:45 pmNAS - VPS
2 stops18h 16mAmerican Airlines
Deal found 10/5$508
This Delta deal was found by Cheapflights users on 10/5. 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.
vie. 11/77:00 amVPS - AUA
1 stop6h 20mDelta
vie. 11/144:35 pmAUA - VPS
1 stop8h 38mDelta
Deal found 10/5$559
This American Airlines deal was found by Cheapflights users on 10/5. 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. 11/74:57 pmVPS - AUA
2 stops21h 53mAmerican Airlines
vie. 11/143:08 pmAUA - VPS
1 stop7h 43mAmerican Airlines
Deal found 10/5$564
This Kiwi.com deal was found by Cheapflights users on 10/4. 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.
dom. 11/166:35 amVPS - SDQ
1 stop31h 51mMultiple Airlines
dom. 11/234:35 pmSDQ - VPS
2 stops33h 01mMultiple Airlines
Deal found 10/4$574

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 octubre 6, 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

sáb. 1/17

7:25 am-9:30 pm

2 stops12h 05m

San Juan Luis Munoz Marin Intl

mar. 4/14

5:05 am-1:10 pm

1 stop9h 05m

$344

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

jue. 2/19

7:00 am-11:20 pm

2 stops14h 20m

San Juan Luis Munoz Marin Intl

mar. 2/24

5:41 am-3:29 pm

2 stops11h 48m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

lun. 11/3

7:15 am-9:30 pm

2 stops12h 15m

San Juan Luis Munoz Marin Intl

lun. 11/10

11:55 am-9:15 pm

2 stops11h 20m

$364

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

mar. 2/10

6:00 am-2:55 pm

1 stop6h 55m

Punta Cana

mar. 2/17

6:10 pm-10:04 am

2 stops17h 54m

$477

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

vie. 2/20

6:00 am-11:00 pm

1 stop15h 00m

Santo Domingo Las Americas

mié. 2/25

6:45 am-11:58 pm

1 stop19h 13m

$485

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

dom. 11/16

7:20 pm-3:45 pm

2 stops18h 25m

Santo Domingo Las Americas

dom. 11/23

6:14 pm-12:01 pm

2 stops19h 47m

$486

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

sáb. 11/1

4:09 pm-12:08 pm

2 stops18h 59m

Nassau Intl

mar. 11/4

7:49 am-8:21 pm

2 stops13h 32m

$508

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

mar. 3/10

6:00 am-1:15 pm

1 stop6h 15m

Santo Domingo Las Americas

mié. 3/11

2:40 pm-8:43 pm

1 stop7h 03m

$516

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

mié. 1/21

6:00 am-12:00 pm

1 stop5h 00m

Nassau Intl

dom. 1/25

6:10 pm-11:08 pm

1 stop5h 58m

$529

ValparaisoMontego Bay

VPS - MBJ

VPSMBJ

Valparaiso Destin-Ft Walton Beach

mar. 2/24

6:00 am-3:15 pm

1 stop8h 15m

Montego Bay Sangster Intl

mar. 3/3

2:05 pm-11:08 pm

1 stop10h 03m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 47 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 octubre 6, 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 octubre 6, 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
8.0
Very good
7,967 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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
8.0
Very good
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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
11,040 reviews
Delta
8.0
Very good
7,967 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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 8h 15m. The time it takes to get you to your destination can typically vary by up to 6h 05m. The distance between Valparaiso, Florida and Caribbean Islands is about 988 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 Southwest, with whom users have recently found tickets for as low as $171. However, be on the lookout for offers from American Airlines and Delta, 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 - Montego Bay Sangster Intl or Valparaiso Destin-Ft Walton Beach - Punta Cana, 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, 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.

See more FAQs

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Alternative routes for Valparaiso to Caribbean Islands

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 Islands

Discover the top 2 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 octubre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$602FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$568FlexibilityNo cancel feeOn-time71%

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