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$171+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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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 September 14, 2025.

Round-trip from

$364
(American Airlines)

One-way from

$171
(Southwest)

Popular in

December

Cheapest in

January

Average price

$434
From Valparaiso Destin-Ft Walton Beach to Caribbean
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One-way flight from Valparaiso Destin-Ft Walton Beach to Caribbean
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Highest demand for flights based on searches. 2% potential increase in price ($11 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 September 2025
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Find 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 September 14, 2025.

This American Airlines deal was found by Cheapflights users on 9/12. 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 12/44:40 pmVPS - SJU
2 stops17h 19mAmerican Airlines
Sun 12/146:00 amSJU - VPS
2 stops17h 24mAmerican Airlines
Deal found 9/12$364
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 9/267:24 pmVPS - SJU
2 stops38h 40mMultiple Airlines
Sat 10/44:51 pmSJU - VPS
1 stop20h 59mMultiple Airlines
Deal found 9/11$372
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Wed 10/296:00 pmVPS - SJU
2 stops18h 45mAmerican Airlines
Mon 11/33:05 pmSJU - VPS
1 stop7h 16mAmerican Airlines
Deal found 9/12$383
This American Airlines deal was found by Cheapflights users on 9/12. 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 11/74:57 pmVPS - SJU
2 stops17h 08mAmerican Airlines
Mon 11/107:00 amSJU - VPS
1 stop13h 35mAmerican Airlines
Deal found 9/12$385
This Southwest deal was found by Cheapflights users on 9/11. 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.
Fri 9/2612:00 pmVPS - SJU
2 stops10h 50mSouthwest
Sat 10/45:00 amSJU - VPS
2 stops12h 50mSouthwest
Deal found 9/11$389
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2210:20 amVPS - SJU
2 stops11h 25mSouthwest
Sun 10/265:05 amSJU - VPS
2 stops11h 50mSouthwest
Deal found 9/12$399
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/94:04 pmVPS - SJU
1 stop6h 50mAmerican Airlines
Tue 10/147:00 amSJU - VPS
2 stops14h 07mAmerican Airlines
Deal found 9/12$425
This American Airlines deal was found by Cheapflights users on 9/12. 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 11/14:09 pmVPS - NAS
2 stops18h 59mAmerican Airlines
Tue 11/410:33 amNAS - VPS
2 stops10h 48mAmerican Airlines
Deal found 9/12$478
This American Airlines deal was found by Cheapflights users on 9/12. 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 12/63:35 pmVPS - SDQ
2 stops18h 53mAmerican Airlines
Fri 12/263:16 pmSDQ - VPS
1 stop10h 42mAmerican Airlines
Deal found 9/12$481
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Mon 10/137:07 amVPS - PUJ
1 stop5h 58mAmerican Airlines
Fri 10/174:55 pmPUJ - VPS
2 stops18h 40mAmerican Airlines
Deal found 9/12$534
This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:30 amVPS - SXM
2 stops12h 00mMultiple Airlines
Sat 10/43:05 pmSXM - VPS
2 stops22h 45mMultiple Airlines
Deal found 9/11$553
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 9/296:01 pmVPS - NAS
2 stops22h 54mAmerican Airlines
Mon 10/610:55 amNAS - VPS
2 stops11h 52mAmerican Airlines
Deal found 9/11$563

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 September 14, 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

Thu 12/4

4:40 pm-11:59 am

2 stops17h 19m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:00 am-9:24 pm

2 stops17h 24m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Thu 2/19

7:00 am-11:20 pm

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Tue 2/24

5:41 am-3:29 pm

2 stops11h 48m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 2/20

7:25 pm-4:55 am

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Tue 2/24

5:41 am-3:29 pm

2 stops11h 48m

$364

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Tue 2/10

7:35 am-3:35 pm

1 stop6h 00m

Punta Cana

Tue 2/17

4:15 pm-11:58 pm

1 stop9h 43m

$472

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Wed 2/11

6:00 am-3:35 pm

1 stop7h 35m

Punta Cana

Wed 2/18

1:45 pm-11:58 pm

2 stops12h 13m

$476

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Sat 11/1

4:09 pm-12:08 pm

2 stops18h 59m

Nassau Intl

Tue 11/4

10:33 am-8:21 pm

2 stops10h 48m

$478

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

Sat 12/6

3:35 pm-12:28 pm

2 stops18h 53m

Santo Domingo Las Americas

Fri 12/26

3:16 pm-11:58 pm

1 stop10h 42m

$481

ValparaisoSanto Domingo

VPS - SDQ

VPSSDQ

Valparaiso Destin-Ft Walton Beach

Tue 3/10

6:00 am-1:15 pm

1 stop6h 15m

Santo Domingo Las Americas

Wed 3/11

2:40 pm-8:43 pm

1 stop7h 03m

$516

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Mon 10/13

6:25 pm-3:17 pm

2 stops19h 52m

Punta Cana

Fri 10/17

4:39 pm-10:35 am

2 stops18h 56m

$534

ValparaisoSimpson Bay

VPS - SXM

VPSSXM

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:30 am-7:30 pm

2 stops12h 00m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-12:50 pm

2 stops22h 45m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 48 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, September is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $254). Flying from Valparaiso, Florida to Caribbean in June 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 September 14, 2025.

When flying from Valparaiso, Florida to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 14, 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
8.0
Very good
7,956 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Overall

8.0

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
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Entertainment

7.9

Overall

8.0

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $171. American Airlines flights start at $217 while deals on Delta start at $285 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 - Punta Cana, 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, September is the cheapest month in which you can book a flight from Valparaiso, Florida to Caribbean (average of $254). Flying from Valparaiso, Florida to Caribbean in June 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$544FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$585FlexibilityNo cancel feeOn-time71%

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