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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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

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.
Mon 12/156:05 amTLH - MBJ
1 stop7h 21mAmerican Airlines
Fri 12/1911:27 amMBJ - TLH
1 stop8h 12mAmerican Airlines
Deal found 10/26$531
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.
Wed 12/106:00 amTLH - SXM
1 stop9h 25mAmerican Airlines
Wed 12/175:25 pmSXM - TLH
1 stop7h 34mAmerican Airlines
Deal found 10/26$548
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 12/138:41 pmTLH - SJU
1 stop12h 28mAmerican Airlines
Sat 12/205:24 amSJU - TLH
1 stop15h 34mAmerican Airlines
Deal found 10/26$560
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.
Tue 11/47:16 amTLH - SJU
1 stop13h 19mAmerican Airlines
Sat 11/1512:55 pmSJU - TLH
1 stop8h 15mAmerican Airlines
Deal found 10/26$570
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:02 pmTLH - SXM
1 stop16h 50mAmerican Airlines
Thu 12/182:59 pmSXM - TLH
1 stop8h 35mAmerican Airlines
Deal found 10/27$573
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.
Thu 12/48:41 pmTLH - MBJ
1 stop13h 32mAmerican Airlines
Mon 12/84:51 pmMBJ - TLH
1 stop6h 48mAmerican Airlines
Deal found 10/26$591
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amTLH - NAS
1 stop14h 12mAmerican Airlines
Mon 12/296:45 pmNAS - TLH
1 stop14h 22mAmerican Airlines
Deal found 10/27$609
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.
Tue 12/308:58 pmTLH - SJU
1 stop11h 37mAmerican Airlines
Thu 1/15:18 amSJU - TLH
1 stop16h 10mAmerican Airlines
Deal found 10/26$619
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amTLH - SJU
1 stop6h 30mAmerican Airlines
Sat 12/2010:03 pmSJU - TLH
1 stop12h 15mAmerican Airlines
Deal found 10/27$630
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:02 pmTLH - MBJ
2 stops16h 58mAmerican Airlines
Thu 12/1811:07 amMBJ - TLH
1 stop9h 21mAmerican Airlines
Deal found 10/27$637
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amTLH - SJU
1 stop7h 21mDelta
Fri 10/312:31 pmSJU - TLH
1 stop8h 05mDelta
Deal found 10/26$645
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.
Mon 10/276:05 amTLH - SJU
1 stop6h 34mAmerican Airlines
Sat 11/17:10 amSJU - TLH
1 stop11h 49mAmerican Airlines
Deal found 10/26$650

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 October 28, 2025.

Round-trip from

$468
(American Airlines)

One-way from

$233
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$545
From Tallahassee to Caribbean
Search Deals
One-way flight from Tallahassee to Caribbean
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 28, 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

Tue 2/17

6:00 am-6:00 pm

2 stops11h 00m

San Juan Luis Munoz Marin Intl

Fri 2/20

7:30 am-10:59 pm

1 stop16h 29m

$415

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 3/3

2:01 pm-10:07 am

2 stops19h 06m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:37 pm-1:26 pm

2 stops21h 49m

$468

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Thu 4/9

7:30 am-1:30 pm

1 stop6h 00m

Nassau Intl

Tue 4/14

1:12 pm-8:46 pm

1 stop7h 34m

$472

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 2/18

6:12 am-6:00 pm

1 stop10h 48m

San Juan Luis Munoz Marin Intl

Fri 2/20

7:00 pm-1:31 pm

2 stops19h 31m

$473

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 2/17

6:00 pm-10:07 am

2 stops15h 07m

San Juan Luis Munoz Marin Intl

Thu 2/19

12:45 pm-11:55 pm

1 stop12h 10m

$473

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Tue 4/14

7:30 am-1:46 pm

1 stop6h 16m

Nassau Intl

Wed 4/15

3:03 pm-10:20 pm

1 stop7h 17m

$475

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Thu 4/9

8:09 pm-11:20 am

2 stops15h 11m

Nassau Intl

Tue 4/14

7:45 am-6:59 pm

1 stop11h 14m

$476

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Sun 3/1

8:40 pm-1:48 pm

1 stop16h 08m

Saint Thomas Island Cyril E King

Fri 3/6

6:36 pm-1:31 pm

2 stops19h 55m

$479

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sun 2/15

6:00 am-11:27 pm

2 stops16h 27m

San Juan Luis Munoz Marin Intl

Fri 2/20

7:00 pm-11:55 pm

1 stop5h 55m

$524

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Thu 2/19

1:56 pm-10:07 am

2 stops19h 11m

San Juan Luis Munoz Marin Intl

Fri 2/20

7:00 pm-1:31 pm

2 stops19h 31m

$524

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, April is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $232). Flying from Tallahassee to Caribbean in September is currently the most expensive (average of $370). 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 October 28, 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 42% 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 October 28, 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
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
5.8
Fair
239 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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. 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 - Montego Bay Sangster Intl or Tallahassee - Nassau Intl 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, April is the cheapest month in which you can book a flight from Tallahassee to Caribbean (average of $232). Flying from Tallahassee to Caribbean in September is currently the most expensive (average of $370). 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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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$456FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$607FlexibilityNo cancel feeOn-time71%

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