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$84+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$132
(Cheapflightsfares)

One-way from

$84
(SmartFares)

Popular in

December

Cheapest in

February

Average price

$231
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).
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Cheapest flight prices on average. 3% potential price decrease ($9 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 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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/108:26 pmTPA - SJU
Nonstop3h 03mFrontier
Thu 10/234:16 pmSJU - TPA
Nonstop3h 10mFrontier
Deal found 9/14$132
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/168:26 pmTPA - SJU
Nonstop3h 03mFrontier
Sat 10/187:58 pmSJU - TPA
Nonstop3h 07mFrontier
Deal found 9/13$133
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/238:26 pmTPA - SJU
Nonstop3h 03mFrontier
Fri 10/312:19 pmSJU - TPA
Nonstop3h 10mFrontier
Deal found 9/13$147
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Mon 11/179:13 amTPA - SJU
Nonstop3h 04mFrontier
Mon 12/87:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 9/13$157
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:26 pmTPA - SJU
Nonstop3h 03mFrontier
Sat 11/17:30 amSJU - TPA
Nonstop3h 08mFrontier
Deal found 9/12$162
This SmartFares deal was found by Cheapflights users on 9/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:05 pmTPA - SJU
Nonstop2h 52mFrontier
Mon 12/87:00 amSJU - TPA
Nonstop3h 21mFrontier
Deal found 9/13$168
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/312:14 pmTPA - SJU
Nonstop3h 08mFrontier
Sun 10/58:00 amSJU - TPA
Nonstop3h 04mFrontier
Deal found 9/13$171
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/296:19 amTPA - SJU
1 stop4h 45mMultiple Airlines
Sat 10/48:00 amSJU - TPA
Nonstop3h 04mMultiple Airlines
Deal found 9/14$174
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:53 pmTPA - SJU
Nonstop3h 05mFrontier
Thu 10/307:30 amSJU - TPA
Nonstop3h 08mFrontier
Deal found 9/12$175
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 12/49:05 pmTPA - SJU
Nonstop2h 52mFrontier
Thu 12/1111:02 amSJU - TPA
Nonstop3h 23mFrontier
Deal found 9/14$176
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Sun 10/1910:03 pmTPA - SJU
Nonstop3h 05mFrontier
Sat 10/257:58 pmSJU - TPA
Nonstop3h 07mFrontier
Deal found 9/14$177
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:19 amTPA - SDQ
1 stop9h 41mSpirit Airlines
Tue 9/305:05 pmSDQ - TPA
1 stop14h 14mSpirit Airlines
Deal found 9/13$242

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 September 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

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sun 2/15

6:00 am-3:15 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Tue 2/24

4:10 pm-8:25 pm

1 stop5h 15m

$227

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sun 2/15

6:00 am-3:15 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Thu 2/19

4:10 pm-8:25 pm

1 stop5h 15m

$227

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sun 2/15

6:00 am-3:15 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Mon 2/23

4:10 pm-8:25 pm

1 stop5h 15m

$227

TampaSaint Thomas Island

TPA - STT

TPASTT

Tampa

Sun 2/15

6:00 am-3:15 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Wed 2/18

4:10 pm-8:25 pm

1 stop5h 15m

$227

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Tue 2/17

8:05 pm-12:08 am

Nonstop3h 03m

San Juan Luis Munoz Marin Intl

Wed 2/18

6:00 am-8:03 am

Nonstop3h 03m

$235

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Wed 10/29

6:00 pm-8:50 pm

Nonstop2h 50m

San Juan Luis Munoz Marin Intl

Mon 11/3

6:01 am-8:07 am

Nonstop3h 06m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Fri 10/31

6:00 pm-8:50 pm

Nonstop2h 50m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:50 pm-9:58 pm

Nonstop3h 08m

$240

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Thu 1/22

3:55 pm-12:35 am

2 stops7h 40m

San Juan Luis Munoz Marin Intl

Thu 1/29

12:10 pm-9:45 pm

2 stops10h 35m

$249

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Fri 10/31

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:15 am-3:29 pm

1 stop9h 14m

$249

TampaSan Juan

TPA - SJU

TPASJU

Tampa

Mon 11/3

4:15 pm-12:35 am

2 stops7h 20m

San Juan Luis Munoz Marin Intl

Wed 11/12

6:40 am-1:40 pm

1 stop8h 00m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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, September is the cheapest month in which you can book a flight from Clearwater to Caribbean (average of $254). Flying from Clearwater 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 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 September 15, 2025.

When flying from Clearwater 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.

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 September 15, 2025.

The most flights from CL9 to 0CB are scheduled on a Friday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 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 September 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
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
2,912 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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 47m. Fly via JetBlue, Spirit Airlines, or Frontier to get the fastest option. The distance from Clearwater to Caribbean is about 1107 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 JetBlue ($107), Frontier ($109), and Southwest ($120).

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

    While some choose either Tampa - Punta Cana or Tampa - Santo Domingo Las Americas, 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: JetBlue (75%), Azul (74%), Frontier( 60%).

  • What are the cheapest flights from Clearwater to Caribbean?

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Tampa - San Juan Luis Munoz Marin Intl) can be booked for $174 on average, our data indicates $321 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, September is the cheapest month in which you can book a flight from Clearwater to Caribbean (average of $254). Flying from Clearwater 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 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$66Average$195FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$90Average$310FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$106Average$312FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$108Average$444FlexibilityNo cancel feeOn-time62%
DeltaCheapest$114Average$494FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$117Average$363FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$176Average$451FlexibilityNo cancel feeOn-time70%
BahamasairCheapest$208Average$318FlexibilityNo cancel feeOn-time33%
United AirlinesCheapest$219Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$548FlexibilityNo cancel feeOn-time71%

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