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$161+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$324
(Southwest)

One-way from

$161
(Southwest)

Popular in

December

Cheapest in

January

Average price

$450
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. 9% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 9/1710:35 amVPS - SJU
1 stop10h 55mSouthwest
Sun 9/2110:30 pmSJU - VPS
2 stops12h 20mSouthwest
Deal found 7/28$324
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/51:47 pmVPS - SJU
1 stop7h 13mDelta
Fri 10/247:15 amSJU - VPS
1 stop9h 56mDelta
Deal found 7/29$364
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 11/74:57 pmVPS - SJU
2 stops17h 08mAmerican Airlines
Mon 11/103:05 pmSJU - VPS
1 stop7h 16mAmerican Airlines
Deal found 7/27$409
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 9/287:10 amVPS - PUJ
1 stop6h 06mAmerican Airlines
Fri 10/33:25 pmPUJ - VPS
1 stop8h 08mAmerican Airlines
Deal found 7/29$469
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/318:30 amVPS - SJU
2 stops28h 47mMultiple Airlines
Fri 9/53:19 pmSJU - VPS
3 stops24h 46mMultiple Airlines
Deal found 7/28$469
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Sun 11/94:40 pmVPS - STT
2 stops20h 35mAmerican Airlines
Sun 11/164:18 pmSTT - VPS
2 stops21h 36mAmerican Airlines
Deal found 7/27$478
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amVPS - NAS
1 stop8h 40mDelta
Tue 9/301:15 pmNAS - VPS
1 stop4h 54mDelta
Deal found 7/27$479
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 8/246:25 pmVPS - NAS
1 stop15h 15mAmerican Airlines
Thu 8/282:27 pmNAS - VPS
1 stop8h 18mAmerican Airlines
Deal found 7/29$483
This Mytrip deal was found by Cheapflights users on 7/27. 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.
Fri 10/33:46 pmVPS - KIN
2 stops19h 16mMultiple Airlines
Fri 10/1712:08 pmKIN - VPS
2 stops19h 10mMultiple Airlines
Deal found 7/27$510
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/263:50 pmVPS - STI
2 stops19h 41mAmerican Airlines
Tue 9/27:00 amSTI - VPS
2 stops9h 13mAmerican Airlines
Deal found 7/28$518
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 9/163:50 pmVPS - CUR
2 stops22h 34mAmerican Airlines
Tue 9/234:25 pmCUR - VPS
2 stops19h 54mAmerican Airlines
Deal found 7/26$523
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/108:10 amVPS - MBJ
1 stop6h 44mAmerican Airlines
Wed 9/171:55 pmMBJ - VPS
1 stop8h 03mAmerican Airlines
Deal found 7/27$534

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 July 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

Wed 9/17

7:00 am-7:45 pm

2 stops11h 45m

San Juan Luis Munoz Marin Intl

Sun 9/21

10:30 pm-9:50 am

2 stops12h 20m

$324

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sun 10/5

1:47 pm-10:00 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Fri 10/24

7:15 am-4:11 pm

1 stop9h 56m

$364

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Fri 11/7

4:57 pm-12:05 pm

2 stops17h 08m

San Juan Luis Munoz Marin Intl

Mon 11/10

3:05 pm-8:21 pm

1 stop7h 16m

$409

ValparaisoSan Juan

VPS - SJU

VPSSJU

Valparaiso Destin-Ft Walton Beach

Sun 8/31

8:30 am-2:17 pm

2 stops28h 47m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:19 pm-3:05 pm

3 stops24h 46m

$469

ValparaisoPunta Cana

VPS - PUJ

VPSPUJ

Valparaiso Destin-Ft Walton Beach

Sun 9/28

7:10 am-2:16 pm

1 stop6h 06m

Punta Cana

Fri 10/3

3:25 pm-10:33 pm

1 stop8h 08m

$469

ValparaisoSaint Thomas Island

VPS - STT

VPSSTT

Valparaiso Destin-Ft Walton Beach

Sun 11/9

4:40 pm-3:15 pm

2 stops20h 35m

Saint Thomas Island Cyril E King

Sun 11/16

4:18 pm-11:54 am

2 stops21h 36m

$478

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Sat 9/27

6:00 am-3:40 pm

1 stop8h 40m

Nassau Intl

Tue 9/30

1:15 pm-5:09 pm

1 stop4h 54m

$479

ValparaisoNassau

VPS - NAS

VPSNAS

Valparaiso Destin-Ft Walton Beach

Sun 8/24

6:25 pm-10:40 am

1 stop15h 15m

Nassau Intl

Thu 8/28

2:27 pm-9:45 pm

1 stop8h 18m

$483

ValparaisoKingston

VPS - KIN

VPSKIN

Valparaiso Destin-Ft Walton Beach

Fri 10/3

3:46 pm-11:02 am

2 stops19h 16m

Kingston Norman Manley

Fri 10/17

12:08 pm-7:18 am

2 stops19h 10m

$510

ValparaisoSantiago de los Caballeros

VPS - STI

VPSSTI

Valparaiso Destin-Ft Walton Beach

Tue 8/26

3:50 pm-12:31 pm

2 stops19h 41m

Santiago de los Caballeros

Tue 9/2

7:00 am-3:13 pm

2 stops9h 13m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 29 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 July 29, 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 July 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
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,972 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $161. American Airlines flights start at $231 while deals on Delta start at $266 one-way.

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

    While some choose either Valparaiso Destin-Ft Walton Beach - Kingston Norman Manley or Valparaiso Destin-Ft Walton Beach - Nassau Intl, 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$551FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$665FlexibilityNo cancel feeOn-time71%

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