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$268+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap flight deals from Tallahassee to Caribbean

Keep the following information in mind while searching for Tallahassee to Caribbean flight deals. Data was last updated septiembre 11, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$268
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$390
From Tallahassee to Caribbean
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One-way flight from Tallahassee to Caribbean
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Highest demand for flights based on searches. 19% potential increase in price ($123 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 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 septiembre 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/11. 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.
sáb. 12/68:02 pmTLH - SJU
1 stop17h 13mAmerican Airlines
vie. 12/122:50 pmSJU - TLH
2 stops9h 49mAmerican Airlines
Deal found 9/11$365
This American Airlines deal was found by Cheapflights users on 9/11. 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.
sáb. 11/88:40 pmTLH - SJU
1 stop14h 25mAmerican Airlines
sáb. 11/158:00 amSJU - TLH
1 stop15h 44mAmerican Airlines
Deal found 9/11$390
This American Airlines deal was found by Cheapflights users on 9/11. 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.
mar. 12/308:58 pmTLH - SJU
1 stop11h 38mAmerican Airlines
jue. 1/110:26 amSJU - TLH
1 stop11h 02mAmerican Airlines
Deal found 9/11$424
This American Airlines deal was found by Cheapflights users on 9/11. 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.
sáb. 10/119:56 amTLH - SJU
1 stop8h 14mAmerican Airlines
mar. 10/147:00 amSJU - TLH
1 stop9h 01mAmerican Airlines
Deal found 9/11$455
This American Airlines deal was found by Cheapflights users on 9/9. 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.
vie. 10/248:43 pmTLH - MHH
1 stop16h 41mAmerican Airlines
vie. 10/312:05 pmMHH - TLH
1 stop6h 05mAmerican Airlines
Deal found 9/9$469
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 11/127:08 pmTLH - STT
2 stops20h 49mAmerican Airlines
mié. 11/194:17 pmSTT - TLH
2 stops20h 21mAmerican Airlines
Deal found 9/10$479
This American Airlines deal was found by Cheapflights users on 9/9. 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.
sáb. 11/228:04 pmTLH - MHH
2 stops17h 19mAmerican Airlines
mar. 11/2512:09 pmMHH - TLH
1 stop11h 50mAmerican Airlines
Deal found 9/9$520
This American Airlines deal was found by Cheapflights users on 9/11. 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.
vie. 9/2610:45 amTLH - SJU
1 stop12h 52mAmerican Airlines
mar. 9/306:10 amSJU - TLH
1 stop10h 53mAmerican Airlines
Deal found 9/11$525
This American Airlines deal was found by Cheapflights users on 9/9. 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.
sáb. 11/158:40 pmTLH - MBJ
1 stop13h 32mAmerican Airlines
mar. 11/184:28 pmMBJ - TLH
1 stop7h 31mAmerican Airlines
Deal found 9/9$531
This American Airlines deal was found by Cheapflights users on 9/9. 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.
dom. 11/168:04 pmTLH - MBJ
2 stops14h 08mAmerican Airlines
jue. 11/201:40 pmMBJ - TLH
2 stops9h 04mAmerican Airlines
Deal found 9/9$574
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 10/86:05 amTLH - MBJ
1 stop8h 25mAmerican Airlines
lun. 10/132:30 pmMBJ - TLH
1 stop24h 31mAmerican Airlines
Deal found 9/10$577
This American Airlines deal was found by Cheapflights users on 9/9. 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.
mié. 10/86:05 amTLH - SJU
1 stop5h 01mAmerican Airlines
dom. 10/127:10 amSJU - TLH
1 stop7h 59mAmerican Airlines
Deal found 9/9$580

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 septiembre 11, 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

sáb. 12/6

8:02 pm-2:15 pm

1 stop17h 13m

San Juan Luis Munoz Marin Intl

vie. 12/12

6:42 pm-11:59 pm

1 stop6h 17m

$365

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 11/8

8:40 pm-12:05 pm

1 stop14h 25m

San Juan Luis Munoz Marin Intl

sáb. 11/15

8:00 am-10:44 pm

1 stop15h 44m

$390

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

mar. 12/30

8:58 pm-9:36 am

1 stop11h 38m

San Juan Luis Munoz Marin Intl

jue. 1/1

10:26 am-8:28 pm

1 stop11h 02m

$424

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 10/11

9:56 am-6:10 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

mar. 10/14

7:00 am-4:01 pm

1 stop9h 01m

$455

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

mar. 3/3

6:23 pm-12:00 pm

2 stops16h 37m

San Juan Luis Munoz Marin Intl

mié. 3/4

6:50 pm-1:15 pm

2 stops19h 25m

$468

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

lun. 2/9

5:35 am-2:55 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

mar. 2/17

2:00 pm-8:47 pm

1 stop7h 47m

$479

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

lun. 1/26

5:49 pm-11:50 am

1 stop17h 01m

Saint Thomas Island Cyril E King

vie. 1/30

4:25 pm-10:02 pm

1 stop6h 37m

$479

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

mié. 11/12

6:00 am-4:57 pm

1 stop9h 57m

Saint Thomas Island Cyril E King

mié. 11/19

4:17 pm-11:38 am

2 stops20h 21m

$479

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

lun. 2/9

6:21 pm-12:10 pm

2 stops16h 49m

Saint Thomas Island Cyril E King

mar. 2/17

6:40 pm-10:35 am

2 stops16h 55m

$479

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

dom. 3/1

8:43 pm-1:45 pm

1 stop16h 02m

Saint Thomas Island Cyril E King

vie. 3/6

6:40 pm-10:35 am

2 stops16h 55m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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, September is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $254). Flying from Tallahassee 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 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 septiembre 11, 2025.

When flying from Tallahassee 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 septiembre 11, 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
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
5.8
Fair
242 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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 10h 59m. Airlines will cover a distance of 915 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 - Montego Bay Sangster Intl, Tallahassee - San Juan Luis Munoz Marin Intl or Tallahassee - Saint Thomas Island Cyril E King 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, September is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $254). Flying from Tallahassee 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

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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$456FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$605FlexibilityNo cancel feeOn-time71%

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