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$233+ Cheap flights from Tallahassee (TLH) 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Tallahassee to Caribbean

Cheapest flights from Tallahassee to Caribbean
Explore the most affordable flight options available from Tallahassee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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.
Tue 12/308:58 pmTLH - SJU
1 stop11h 37mAmerican Airlines
Thu 1/16:57 pmSJU - TLH
1 stop15h 10mAmerican Airlines
Deal found 12/11$494
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/288:24 pmTLH - SJU
1 stop14h 33mAmerican Airlines
Wed 12/3110:03 pmSJU - TLH
1 stop12h 04mAmerican Airlines
Deal found 12/10$535
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Fri 12/268:39 pmTLH - SJU
1 stop11h 56mAmerican Airlines
Thu 1/16:57 pmSJU - TLH
1 stop15h 10mAmerican Airlines
Deal found 12/11$560
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/288:24 pmTLH - SJU
1 stop12h 11mAmerican Airlines
Wed 1/71:24 pmSJU - TLH
1 stop20h 52mAmerican Airlines
Deal found 12/10$606
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/256:32 amTLH - SJU
1 stop5h 58mAmerican Airlines
Mon 12/2910:03 pmSJU - TLH
1 stop12h 04mAmerican Airlines
Deal found 12/10$675
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Fri 12/268:39 pmTLH - SJU
1 stop11h 56mAmerican Airlines
Tue 12/305:24 amSJU - TLH
1 stop16h 04mAmerican Airlines
Deal found 12/11$700
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Tue 12/239:48 amTLH - MBJ
1 stop5h 37mAmerican Airlines
Fri 12/262:23 pmMBJ - TLH
1 stop5h 46mAmerican Airlines
Deal found 12/11$719
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/142:14 pmTLH - SJU
1 stop6h 51mAmerican Airlines
Tue 12/168:20 amSJU - TLH
1 stop7h 01mAmerican Airlines
Deal found 12/10$745
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:30 amTLH - SJU
1 stop6h 15mDelta
Wed 12/177:00 amSJU - TLH
1 stop8h 04mDelta
Deal found 12/11$755
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Tue 12/166:05 amTLH - NAS
1 stop7h 50mAmerican Airlines
Thu 12/186:45 pmNAS - TLH
1 stop5h 50mAmerican Airlines
Deal found 12/12$766
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/228:04 pmTLH - SJU
1 stop14h 35mAmerican Airlines
Fri 1/25:24 amSJU - TLH
1 stop19h 35mAmerican Airlines
Deal found 12/10$849
This American Airlines deal was found by Cheapflights users on 12/9. 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 12/256:10 amTLH - STT
1 stop5h 30mAmerican Airlines
Mon 12/296:36 pmSTT - TLH
2 stops18h 11mAmerican Airlines
Deal found 12/9$859

Find flight deals from Tallahassee to Caribbean

Keep the following information in mind while searching for Tallahassee to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$233
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$680
From Tallahassee to Caribbean
Search Deals
One-way flight from Tallahassee to Caribbean
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallahassee 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 12, 2025.
Use the filters below to find and compare flights from Tallahassee to Caribbean that are best for you.

Fly from

Tallahassee

Fly to

Caribbean

Route

Depart

Return

Price

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Mon 4/6

7:55 pm-10:35 am

1 stop14h 40m

San Juan Luis Munoz Marin Intl

Wed 4/8

6:55 pm-11:59 pm

1 stop5h 04m

$365

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Fri 1/9

6:00 am-1:08 pm

1 stop6h 08m

San Juan Luis Munoz Marin Intl

Tue 1/13

8:20 am-2:15 pm

1 stop6h 55m

$405

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 2/11

6:00 am-6:22 pm

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Sun 2/15

8:15 am-8:10 pm

1 stop12h 55m

$415

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sat 4/4

8:44 pm-9:00 am

1 stop12h 16m

San Juan Luis Munoz Marin Intl

Sat 4/11

6:55 pm-9:56 am

1 stop15h 01m

$440

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 4/8

6:28 am-4:05 pm

1 stop9h 37m

San Juan Luis Munoz Marin Intl

Sat 4/11

6:55 pm-11:59 pm

1 stop5h 04m

$440

TallahasseePunta Cana

TLH - PUJ

TLHPUJ

Tallahassee

Sat 1/31

6:53 pm-12:55 pm

1 stop17h 02m

Punta Cana

Tue 2/3

4:09 pm-11:57 pm

1 stop8h 48m

$474

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Tue 3/31

7:06 pm-1:02 pm

2 stops17h 56m

Saint Thomas Island Cyril E King

Wed 4/8

6:40 pm-9:56 am

1 stop15h 16m

$479

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Thu 2/26

6:13 am-12:21 pm

1 stop5h 08m

Saint Thomas Island Cyril E King

Mon 3/2

12:50 pm-7:37 pm

1 stop7h 47m

$479

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 12/30

8:58 pm-11:57 am

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Thu 1/1

6:57 pm-9:07 am

1 stop15h 10m

$494

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Mon 1/19

10:11 am-5:02 pm

1 stop6h 51m

Nassau Intl

Fri 1/23

2:56 pm-8:45 pm

1 stop5h 49m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 34 results
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Best time to book a flight from Tallahassee to Caribbean

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

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

Currently, June is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $239). Flying from Tallahassee to Caribbean in December is currently the most expensive (average of $383). 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 TLH to CB?

Find hourly flight availability from Tallahassee 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 12, 2025.

One of the essential ways to save on airfare from Tallahassee to Caribbean is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 52% on airfare.

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 12, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and Silver Airways from Tallahassee to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
11,049 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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.
Silver Airways
5.7
Fair
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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 Tallahassee 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 Tallahassee to Caribbean?

    For a flight from Tallahassee to Caribbean, you will be flying from Tallahassee. Tallahassee (TLH) is just 5.0 mi from the center of the city.

  • How long is the flight from Tallahassee to Caribbean?

    Departing from Tallahassee to Caribbean will take you 6h 51m. Airlines will cover a distance of 560 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    When deciding which route to take from Tallahassee to Caribbean consider Tallahassee - San Juan Luis Munoz Marin Intl, Tallahassee - Punta Cana or Tallahassee - Castries Hewanorra as they are the most popular.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $239). Flying from Tallahassee to Caribbean in December is currently the most expensive (average of $383). 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 Tallahassee 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 Tallahassee to Caribbean

Discover the top 2 airlines that operate flights from Tallahassee 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$467FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$606FlexibilityNo cancel feeOn-time71%

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