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$273+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$495
(American Airlines)

One-way from

$273
(Delta)

Popular in

December

Cheapest in

January

Average price

$549
From Tallahassee to Caribbean
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One-way flight from Tallahassee to Caribbean
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High demand for flights, 1% potential price rise
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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 July 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/28. 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 9/216:15 amTLH - SJU
1 stop4h 56mAmerican Airlines
Thu 9/2512:01 pmSJU - TLH
1 stop11h 49mAmerican Airlines
Deal found 7/28$495
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/106:15 amTLH - UVF
1 stop8h 01mAmerican Airlines
Wed 9/173:17 pmUVF - TLH
1 stop8h 33mAmerican Airlines
Deal found 7/27$563
This American Airlines deal was found by Cheapflights users on 7/28. 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 12/56:22 amTLH - MBJ
1 stop7h 43mAmerican Airlines
Mon 12/81:05 pmMBJ - TLH
1 stop11h 00mAmerican Airlines
Deal found 7/28$565
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/106:05 amTLH - SXM
1 stop9h 10mAmerican Airlines
Sun 11/163:20 pmSXM - TLH
1 stop9h 36mAmerican Airlines
Deal found 7/29$588
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Tue 8/266:20 amTLH - BGI
1 stop7h 44mAmerican Airlines
Fri 8/293:00 pmBGI - TLH
1 stop8h 58mAmerican Airlines
Deal found 7/27$601
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/148:19 pmTLH - PUJ
1 stop14h 36mAmerican Airlines
Wed 8/2011:55 amPUJ - TLH
1 stop12h 03mAmerican Airlines
Deal found 7/29$666
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Sun 8/176:20 amTLH - SKB
1 stop7h 02mAmerican Airlines
Thu 8/212:30 pmSKB - TLH
1 stop9h 28mAmerican Airlines
Deal found 7/27$784
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/215:40 amTLH - SJU
1 stop10h 35mDelta
Fri 11/281:50 pmSJU - TLH
1 stop7h 57mDelta
Deal found 7/27$1,445
This WestJet deal was found by Cheapflights users on 7/28. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2010:20 amTLH - MBJ
2 stops56h 04mWestJet
Sun 11/231:25 pmMBJ - TLH
2 stops29h 22mWestJet
Deal found 7/28$1,649
This WestJet deal was found by Cheapflights users on 7/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1512:46 pmTLH - PUJ
2 stops20h 12mWestJet
Mon 8/183:35 pmPUJ - TLH
2 stops41h 47mWestJet
Deal found 7/27$1,665
This SmartFares deal was found by Cheapflights users on 7/28. 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 8/12:44 pmTLH - PUJ
2 stops21h 41mLATAM Airlines
Thu 8/72:45 amPUJ - TLH
2 stops20h 07mLATAM Airlines
Deal found 7/28$4,251

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 July 29, 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

Sun 9/21

6:15 am-11:11 am

1 stop4h 56m

San Juan Luis Munoz Marin Intl

Thu 9/25

12:01 pm-11:50 pm

1 stop11h 49m

$495

TallahasseeCastries

TLH - UVF

TLHUVF

Tallahassee

Wed 9/10

6:15 am-2:16 pm

1 stop8h 01m

Castries Hewanorra

Wed 9/17

3:17 pm-11:50 pm

1 stop8h 33m

$563

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Thu 1/15

5:35 am-12:50 pm

1 stop6h 15m

Saint Thomas Island Cyril E King

Mon 1/19

3:00 pm-10:22 pm

1 stop8h 22m

$567

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Wed 9/3

6:15 am-1:38 pm

1 stop8h 23m

Montego Bay Sangster Intl

Mon 9/8

3:36 pm-12:44 pm

2 stops20h 08m

$570

TallahasseeSimpson Bay

TLH - SXM

TLHSXM

Tallahassee

Fri 10/10

6:05 am-3:15 pm

1 stop9h 10m

Simpson Bay Princess Juliana

Sun 11/16

3:20 pm-11:56 pm

1 stop9h 36m

$588

TallahasseeBridgetown

TLH - BGI

TLHBGI

Tallahassee

Tue 8/26

6:20 am-2:04 pm

1 stop7h 44m

Bridgetown Grantley Adams Intl

Fri 8/29

3:00 pm-11:58 pm

1 stop8h 58m

$601

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Thu 1/15

8:39 pm-12:10 pm

1 stop14h 31m

Saint Thomas Island Cyril E King

Mon 1/19

4:35 pm-10:41 am

2 stops19h 06m

$622

TallahasseePunta Cana

TLH - PUJ

TLHPUJ

Tallahassee

Thu 8/14

8:19 pm-10:55 am

1 stop14h 36m

Punta Cana

Wed 8/20

11:55 am-11:58 pm

1 stop12h 03m

$666

TallahasseeBasseterre

TLH - SKB

TLHSKB

Tallahassee

Sun 8/17

6:20 am-1:22 pm

1 stop7h 02m

Basseterre Robert Bradshaw Intl

Thu 8/21

2:30 pm-11:58 pm

1 stop9h 28m

$784

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Fri 11/21

5:40 am-5:15 pm

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Fri 11/28

1:50 pm-8:47 pm

1 stop7h 57m

$1,445

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 15 results
1
2

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 July 29, 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 July 29, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and WestJet 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
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

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
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

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
10,000 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

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.
WestJet
7.2
Good
2,972 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

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.

  • 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 - Montego Bay Sangster 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, 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$456FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$591FlexibilityNo cancel feeOn-time71%

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