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$89+ Cheap flights from Clearwater, FL 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Clearwater to Caribbean

Cheapest flights from Clearwater to Caribbean
Explore the most affordable flight options available from Clearwater to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:00 pmTPA - SJU
Nonstop2h 56mFrontier
Fri 12/124:24 pmSJU - TPA
Nonstop3h 26mFrontier
Deal found 10/27$161
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:00 pmTPA - SJU
Nonstop2h 56mFrontier
Sat 12/68:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 10/28$162
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:00 pmTPA - SJU
Nonstop2h 56mFrontier
Sun 12/77:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 10/28$163
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:38 amTPA - SJU
Nonstop3h 04mFrontier
Sat 11/226:52 pmSJU - TPA
Nonstop3h 16mFrontier
Deal found 10/29$164
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:04 pmTPA - SJU
Nonstop3h 05mFrontier
Mon 11/246:10 amSJU - TPA
Nonstop3h 13mFrontier
Deal found 10/28$170
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:00 pmTPA - SJU
Nonstop2h 56mFrontier
Thu 12/117:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 10/29$176
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:00 pmTPA - SJU
Nonstop2h 56mFrontier
Sun 12/147:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 10/27$178
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:38 amTPA - SJU
Nonstop3h 04mFrontier
Fri 11/216:10 amSJU - TPA
Nonstop3h 13mFrontier
Deal found 10/29$182
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:38 amTPA - SJU
Nonstop3h 04mFrontier
Fri 11/216:10 amSJU - TPA
Nonstop3h 13mFrontier
Deal found 10/29$184
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2711:41 amTPA - SJU
1 stop12h 25mFrontier
Thu 12/47:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 10/28$186
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.
Sat 12/136:00 amTPA - STT
1 stop9h 58mAmerican Airlines
Thu 12/186:36 pmSTT - TPA
1 stop14h 07mAmerican Airlines
Deal found 10/26$227
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:45 amTPA - STT
1 stop5h 15mSpirit Airlines
Sun 11/232:00 pmSTT - TPA
1 stop10h 51mSpirit Airlines
Deal found 10/28$248

Cheap flight deals from Clearwater to Caribbean

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

Round-trip from

$161
(Kiwi.com)

One-way from

$89
(Frontier)

Popular in

December

Cheapest in

February

Average price

$249
From Clearwater to Caribbean
Search Deals
One-way flight from Clearwater to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 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 Clearwater 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 October 29, 2025.
Use the filters below to find and compare flights from Clearwater to Caribbean that are best for you.

Fly from

Clearwater

Fly to

Caribbean

Route

Depart

Return

Price

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Thu 12/18

6:00 am-9:48 am

Nonstop2h 48m

San Juan Luis Munoz Marin Intl

Tue 12/23

3:45 pm-6:00 pm

Nonstop3h 15m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Sun 2/8

11:20 am-3:15 pm

Nonstop2h 55m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:55 pm-9:15 pm

Nonstop3h 20m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Sun 2/1

3:25 pm-7:19 pm

Nonstop2h 54m

San Juan Luis Munoz Marin Intl

Sun 2/8

6:00 am-8:16 am

Nonstop3h 16m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Fri 12/5

8:05 pm-11:57 pm

Nonstop2h 52m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:01 am-8:08 am

Nonstop3h 07m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Thu 1/22

3:25 pm-7:19 pm

Nonstop2h 54m

San Juan Luis Munoz Marin Intl

Sun 1/25

6:00 am-8:16 am

Nonstop3h 16m

$250

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Thu 1/22

8:27 pm-12:28 pm

1 stop15h 01m

Saint Thomas Island Cyril E King

Fri 1/30

1:33 pm-10:18 pm

1 stop9h 45m

$252

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Fri 1/23

8:27 pm-12:28 pm

1 stop15h 01m

Saint Thomas Island Cyril E King

Fri 1/30

1:33 pm-10:18 pm

1 stop9h 45m

$252

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Sat 2/14

5:00 pm-8:55 pm

Nonstop2h 55m

San Juan Luis Munoz Marin Intl

Wed 2/18

2:35 pm-5:05 pm

Nonstop3h 30m

$265

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sat 11/15

9:37 pm-1:00 pm

1 stop14h 23m

Saint Thomas Island Cyril E King

Thu 11/20

2:00 pm-11:51 pm

1 stop10h 51m

$267

TampaSimpson Bay

TPA - SXM

TPASXM

Tampa

Sat 1/10

6:46 am-3:10 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Sat 1/24

4:28 pm-10:18 pm

1 stop6h 50m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Best time to book a flight from Clearwater to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Clearwater 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 Clearwater to Caribbean

What is the cheapest month to book a flight from Clearwater to Caribbean?

Currently, August is the cheapest month in which you can book a flight from Clearwater to Caribbean (average of $53). Flying from Clearwater to Caribbean in September is currently the most expensive (average of $110). 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 CL9 to CB?

Find hourly flight availability from Clearwater 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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Clearwater to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Clearwater to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Clearwater to Caribbean. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Clearwater to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 29, 2025.
See what other customers who have flown with Southwest, American Airlines, and JetBlue from Clearwater 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

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
Spirit Airlines
6.3
Okay
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
Frontier
5.8
Fair
3,124 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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 Clearwater to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Clearwater to Caribbean?

    There are many flights that can get you from Clearwater to Caribbean in 2h 48m. Fly via JetBlue, Southwest, or Spirit Airlines to get the fastest option. The distance from Clearwater to Caribbean is about 1236 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Clearwater to Caribbean one-way?

    The cheapest airlines for a one-way flight from Clearwater to Caribbean are Delta ($94), Frontier ($109), and Spirit Airlines ($111).

  • What are the most popular routes from Clearwater to Caribbean?

    While some choose either Tampa - Santo Domingo Las Americas or Tampa - Punta Cana, Tampa - San Juan Luis Munoz Marin Intl is the most popular route from Clearwater to Caribbean.

  • What are the most reliable airlines from Clearwater to Caribbean?

    Before booking your flight to Caribbean from Clearwater, check out the most reliable airlines to get you to your destination on time: Frontier (78%), Spirit Airlines (76%), Azul( 75%).

  • What are the cheapest flights from Clearwater to Caribbean?

    Looking at all options, your cheapest flight can be booked for $94. While the most popular route (Tampa - San Juan Luis Munoz Marin Intl) can be booked for $188 on average, our data indicates $218 when flying from Clearwater to Caribbean.

  • Can I find deals for flights from Clearwater to Caribbean that include hotel bookings?

    Yes. In addition to deals on Clearwater to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Clearwater to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Clearwater to Caribbean.

  • Can I find deals for business class flights from Clearwater to Caribbean?

    Yes. Cheapflights offers flight deals from Clearwater 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 Clearwater to Caribbean?

    Currently, August is the cheapest month in which you can book a flight from Clearwater to Caribbean (average of $53). Flying from Clearwater to Caribbean in September is currently the most expensive (average of $110). 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 Clearwater to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Clearwater to Caribbean

Discover the top 10 airlines that operate flights from Clearwater 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$196FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$88Average$365FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$92Average$318FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$109Average$442FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$110Average$314FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$507FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$176Average$428FlexibilityNo cancel feeOn-time70%
BahamasairCheapest$203Average$322FlexibilityNo cancel feeOn-time33%
ArajetCheapest$205Average$275FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$478FlexibilityNo cancel feeOn-time69%

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