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$209+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
feb. 25 — mar. 41
mié. 2/25
mié. 3/4
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 enero 26, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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.
lun. 4/67:55 pm
TLH
-
SJU
1 stop16h 08m
American Airlines
mié. 4/86:47 am
SJU
-
TLH
1 stop11h 19m
American Airlines
Deal found 1/26$386
This American Airlines deal was found by Cheapflights users on 1/26. 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.
mié. 4/86:09 am
TLH
-
SJU
1 stop8h 43m
American Airlines
sáb. 4/1111:43 am
SJU
-
TLH
1 stop12h 13m
American Airlines
Deal found 1/26$411
This American Airlines deal was found by Cheapflights users on 1/23. 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. 2/287:55 pm
TLH
-
SJU
1 stop16h 58m
American Airlines
lun. 3/27:01 pm
SJU
-
TLH
1 stop16h 17m
American Airlines
Deal found 1/23$426
This American Airlines deal was found by Cheapflights users on 1/26. 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.
sáb. 4/46:10 am
TLH
-
SJU
1 stop4h 46m
American Airlines
sáb. 4/1111:43 am
SJU
-
TLH
1 stop12h 13m
American Airlines
Deal found 1/26$436
This American Airlines deal was found by Cheapflights users on 1/26. 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.
dom. 4/58:51 pm
TLH
-
SJU
1 stop14h 05m
American Airlines
sáb. 4/1111:43 am
SJU
-
TLH
1 stop12h 13m
American Airlines
Deal found 1/26$451
This American Airlines deal was found by Cheapflights users on 1/23. 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.
lun. 2/166:00 am
TLH
-
SJU
1 stop8h 11m
American Airlines
lun. 2/2310:50 am
SJU
-
TLH
1 stop14h 09m
American Airlines
Deal found 1/23$471
This American Airlines deal was found by Cheapflights users on 1/26. 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.
vie. 4/38:51 pm
TLH
-
SJU
1 stop14h 05m
American Airlines
sáb. 4/1111:43 am
SJU
-
TLH
1 stop12h 13m
American Airlines
Deal found 1/26$476
This American Airlines deal was found by Cheapflights users on 1/26. 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.
lun. 5/186:09 am
TLH
-
NAS
1 stop3h 20m
American Airlines
jue. 5/216:22 pm
NAS
-
TLH
1 stop5h 37m
American Airlines
Deal found 1/26$494
This American Airlines deal was found by Cheapflights users on 1/24. 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. 9/308:01 pm
TLH
-
STT
2 stops16h 49m
American Airlines
jue. 10/85:40 pm
STT
-
TLH
1 stop16h 14m
American Airlines
Deal found 1/24$500
This American Airlines deal was found by Cheapflights users on 1/26. 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.
sáb. 7/118:42 pm
TLH
-
SJU
1 stop14h 13m
American Airlines
dom. 7/196:00 am
SJU
-
TLH
1 stop14h 12m
American Airlines
Deal found 1/26$501
This American Airlines deal was found by Cheapflights users on 1/25. 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. 6/39:47 am
TLH
-
PUJ
1 stop6h 58m
American Airlines
sáb. 6/64:17 pm
PUJ
-
TLH
1 stop17h 00m
American Airlines
Deal found 1/25$529
This American Airlines deal was found by Cheapflights users on 1/25. 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. 4/246:09 am
TLH
-
STT
1 stop6h 56m
American Airlines
lun. 5/44:34 pm
STT
-
TLH
2 stops21h 35m
American Airlines
Deal found 1/25$530

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 enero 26, 2026.

Round-trip from

$386
(American Airlines)

One-way from

$209
(Delta)

Popular in

July

Cheapest in

March

Average price

$495
From Tallahassee to Caribbean
Search Deals
One-way flight from Tallahassee to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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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 enero 26, 2026.
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

lun. 4/6

7:55 pm-12:03 pm

1 stop16h 08m

San Juan Luis Munoz Marin Intl

mié. 4/8

7:25 am-10:41 pm

1 stop15h 16m

$386

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 3/28

8:51 pm-9:00 am

1 stop12h 09m

San Juan Luis Munoz Marin Intl

sáb. 4/4

1:23 pm-12:09 am

1 stop10h 46m

$411

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 2/28

7:55 pm-1:53 pm

1 stop16h 58m

San Juan Luis Munoz Marin Intl

lun. 3/2

7:01 pm-10:18 am

1 stop16h 17m

$426

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 4/4

6:10 am-10:56 am

1 stop4h 46m

San Juan Luis Munoz Marin Intl

sáb. 4/11

11:43 am-11:56 pm

1 stop12h 13m

$436

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

jue. 2/26

3:41 pm-11:58 pm

1 stop7h 17m

San Juan Luis Munoz Marin Intl

mar. 3/3

6:15 am-2:53 pm

1 stop9h 38m

$451

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

sáb. 2/28

8:48 pm-1:33 pm

1 stop15h 45m

San Juan Luis Munoz Marin Intl

sáb. 3/7

7:00 am-8:18 pm

1 stop14h 18m

$451

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

dom. 4/5

8:51 pm-10:56 am

1 stop14h 05m

San Juan Luis Munoz Marin Intl

sáb. 4/11

11:43 am-11:56 pm

1 stop12h 13m

$451

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

mié. 4/8

6:09 am-6:06 pm

1 stop11h 57m

San Juan Luis Munoz Marin Intl

sáb. 4/11

6:01 pm-11:56 pm

1 stop5h 55m

$451

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

lun. 5/18

12:11 pm-8:27 pm

2 stops8h 16m

Nassau Intl

jue. 5/21

6:22 pm-11:59 pm

1 stop5h 37m

$494

TallahasseePunta Cana

TLH - PUJ

TLHPUJ

Tallahassee

mié. 6/3

9:47 am-4:45 pm

1 stop6h 58m

Punta Cana

sáb. 6/6

4:17 pm-9:17 am

1 stop17h 00m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 39 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 January is currently the most expensive (average of $390). 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.

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 enero 26, 2026.
Read reviews from past customers who have flown Delta and American Airlines 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
8,111 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

7.9

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
8,111 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

7.9

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
11,189 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Overall

7.9

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 16h 08m. Airlines will cover a distance of 1415 mi.

  • 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 - 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 January is currently the most expensive (average of $390). 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 enero 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$425FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$385Average$613FlexibilityNo cancel feeOn-time71%

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