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$72+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Super.com deal was found by Cheapflights users on 12/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:00 amTPA - SJU
1 stop17h 06mFrontier
Mon 3/26:00 amSJU - TPA
1 stop15h 00mFrontier
Deal found 12/14$145
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:00 amTPA - SJU
1 stop17h 06mFrontier
Tue 1/133:47 pmSJU - TPA
Nonstop3h 26mFrontier
Deal found 12/14$181
This CheapOair deal was found by Cheapflights users on 12/14. 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.
Tue 12/305:33 pmTPA - SJU
1 stop30h 51mFrontier
Sun 1/112:29 amSJU - TPA
1 stop18h 34mFrontier
Deal found 12/14$193
This CheapOair deal was found by Cheapflights users on 12/14. 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.
Tue 12/305:33 pmTPA - SJU
1 stop30h 51mFrontier
Tue 1/133:47 pmSJU - TPA
Nonstop3h 26mFrontier
Deal found 12/14$194
This eDestinos deal was found by Cheapflights users on 12/13. 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.
Mon 12/228:31 amTPA - SJU
1 stop12h 34mSpirit Airlines
Tue 12/234:10 amSJU - TPA
1 stop4h 26mSpirit Airlines
Deal found 12/13$196
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Sat 12/206:08 pmTPA - SJU
1 stop30h 16mFrontier
Tue 12/234:19 pmSJU - TPA
1 stop9h 07mFrontier
Deal found 12/13$212
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/2210:53 amTPA - SJU
1 stop10h 12mMultiple Airlines
Wed 12/242:44 pmSJU - TPA
1 stop10h 24mMultiple Airlines
Deal found 12/14$213
This Cheapflightsfares deal was found by Cheapflights users on 12/14. 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.
Fri 12/198:31 amTPA - SXM
1 stop4h 44mSpirit Airlines
Mon 12/223:20 pmSXM - TPA
1 stop5h 48mSpirit Airlines
Deal found 12/14$272
This Frontier deal was found by Cheapflights users on 12/14. 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.
Tue 12/305:01 amTPA - PUJ
1 stop8h 28mFrontier
Wed 12/311:28 pmPUJ - TPA
1 stop9h 00mFrontier
Deal found 12/14$295
This Priceline deal was found by Cheapflights users on 12/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:25 amTPA - GCM
1 stop5h 30mMultiple Airlines
Thu 12/182:40 pmGCM - TPA
1 stop5h 28mMultiple Airlines
Deal found 12/13$300
This Expedia deal was found by Cheapflights users on 12/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:03 pmTPA - PUJ
1 stop18h 47mSpirit Airlines
Sun 12/286:08 pmPUJ - TPA
1 stop14h 28mSpirit Airlines
Deal found 12/14$301
This Frontier deal was found by Cheapflights users on 12/14. 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.
Sun 12/285:45 amTPA - PUJ
1 stop7h 26mFrontier
Wed 12/311:28 pmPUJ - TPA
1 stop9h 00mFrontier
Deal found 12/14$310

Find flight deals from Clearwater to Caribbean

Keep the following information in mind while searching for Clearwater to Caribbean flight deals. Data was last updated December 15, 2025.

Round-trip from

$141
(Frontier)

One-way from

$72
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$351
From Clearwater to Caribbean
Search Deals
One-way flight from Clearwater to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 15, 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 3/19

10:00 am-12:59 pm

Nonstop2h 59m

San Juan Luis Munoz Marin Intl

Sun 3/22

5:30 am-9:00 am

Nonstop3h 30m

$193

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Thu 3/12

2:38 pm-12:44 am

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Sun 3/15

5:30 am-9:00 am

Nonstop3h 30m

$196

TampaChristiansted

TPA - STX

TPASTX

Tampa

Fri 2/6

8:38 am-3:43 pm

1 stop6h 05m

Christiansted Henry Rohlsen

Mon 2/9

4:38 pm-8:49 pm

1 stop5h 11m

$218

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Mon 2/23

7:00 am-3:20 pm

1 stop7h 20m

Saint Thomas Island Cyril E King

Mon 3/2

4:10 pm-11:53 pm

1 stop8h 43m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Thu 1/8

7:00 am-3:05 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

Mon 1/12

3:10 pm-9:12 pm

1 stop7h 02m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Fri 1/23

6:00 am-5:05 pm

1 stop10h 05m

Saint Thomas Island Cyril E King

Mon 1/26

6:39 pm-7:57 am

1 stop14h 18m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sun 1/11

5:30 am-12:42 pm

1 stop6h 12m

Saint Thomas Island Cyril E King

Thu 1/15

4:15 pm-12:25 am

1 stop9h 10m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Fri 1/9

7:00 am-5:05 pm

1 stop9h 05m

Saint Thomas Island Cyril E King

Sun 1/11

6:39 pm-9:45 am

1 stop16h 06m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Wed 2/25

6:00 am-3:20 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

Mon 3/2

1:16 pm-6:15 pm

1 stop5h 59m

$221

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Fri 1/23

7:00 am-5:05 pm

1 stop9h 05m

Saint Thomas Island Cyril E King

Fri 1/30

6:39 pm-8:18 am

1 stop14h 39m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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 November is currently the most expensive (average of $113). 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 December 15, 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 December 13, 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.

Weekly flight availability from Clearwater to Caribbean

Explore weekly flight availability from Clearwater to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 15, 2025.

The most flights from CL9 to 0CB are scheduled on a Friday (22 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 on average).

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 December 15, 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
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,051 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,894 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,182 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 59m. Fly via Frontier, Spirit Airlines, or American 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 Frontier ($54), Spirit Airlines ($78), and JetBlue ($97).

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

    While some choose either Tampa - Punta Cana or Tampa - Saint Thomas Island Cyril E King, 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: Spirit Airlines (89%), Frontier (88%), Azul( 69%).

  • What are the cheapest flights from Clearwater to Caribbean?

    Looking at all options, your cheapest flight can be booked for $80. While the most popular route (Tampa - San Juan Luis Munoz Marin Intl) can be booked for $149 on average, our data indicates $213 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 November is currently the most expensive (average of $113). 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$197FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$84Average$365FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$93Average$313FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$493FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$110Average$307FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$112Average$430FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$167Average$410FlexibilityNo cancel feeOn-time70%
BahamasairCheapest$196Average$325FlexibilityNo cancel feeOn-time33%
ArajetCheapest$204Average$240FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$220Average$467FlexibilityNo cancel feeOn-time69%

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