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Caribbean Islands

$233+ Cheap flights from Tallahassee (TLH) to Caribbean Islands

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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap flight deals from Tallahassee to Caribbean Islands

Keep the following information in mind while searching for Tallahassee to Caribbean Islands flight deals. Data was last updated October 14, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$233
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$514
From Tallahassee to Caribbean Islands
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One-way flight from Tallahassee to Caribbean Islands
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Highest demand for flights based on searches. 18% potential increase in price ($115 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Tallahassee to Caribbean Islands

Cheapest flights from Tallahassee to Caribbean Islands
Explore the most affordable flight options available from Tallahassee to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/13. 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 11/57:08 pmTLH - SJU
2 stops14h 09mAmerican Airlines
Fri 12/55:56 pmSJU - TLH
1 stop6h 43mAmerican Airlines
Deal found 10/13$405
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/88:40 pmTLH - SJU
1 stop16h 03mAmerican Airlines
Wed 11/122:47 pmSJU - TLH
2 stops9h 45mAmerican Airlines
Deal found 10/13$425
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/48:40 pmTLH - SJU
1 stop16h 03mAmerican Airlines
Mon 11/176:42 pmSJU - TLH
1 stop6h 17mAmerican Airlines
Deal found 10/13$455
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/148:40 pmTLH - SJU
1 stop12h 37mAmerican Airlines
Mon 11/1711:13 amSJU - TLH
1 stop13h 46mAmerican Airlines
Deal found 10/13$460
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Thu 11/209:59 amTLH - SJU
1 stop13h 45mAmerican Airlines
Sat 12/2010:25 amSJU - TLH
1 stop10h 33mAmerican Airlines
Deal found 10/12$520
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/296:00 amTLH - STT
1 stop6h 51mAmerican Airlines
Fri 12/56:17 pmSTT - TLH
2 stops18h 28mAmerican Airlines
Deal found 10/13$534
This American Airlines deal was found by Cheapflights users on 10/14. 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 11/166:01 pmTLH - SJU
1 stop11h 09mAmerican Airlines
Mon 12/2910:03 pmSJU - TLH
1 stop12h 04mAmerican Airlines
Deal found 10/14$535
This American Airlines deal was found by Cheapflights users on 10/13. 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 10/249:56 amTLH - SJU
1 stop8h 14mAmerican Airlines
Mon 10/277:00 pmSJU - TLH
1 stop4h 58mAmerican Airlines
Deal found 10/13$545
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/126:00 amTLH - SJU
1 stop6h 43mAmerican Airlines
Sun 11/1611:13 amSJU - TLH
1 stop5h 18mAmerican Airlines
Deal found 10/13$555
This American Airlines deal was found by Cheapflights users on 10/14. 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 12/228:28 pmTLH - SJU
1 stop12h 07mAmerican Airlines
Mon 1/127:12 pmSJU - TLH
1 stop5h 45mAmerican Airlines
Deal found 10/14$573
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/412:00 pmTLH - SJU
1 stop7h 48mAmerican Airlines
Sun 11/1611:13 amSJU - TLH
1 stop9h 57mAmerican Airlines
Deal found 10/13$575
This American Airlines deal was found by Cheapflights users on 10/13. 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 12/811:13 amMBJ - TLH
1 stop12h 46mAmerican Airlines
Deal found 10/13$581

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tallahassee to Caribbean Islands 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 14, 2025.
Use the filters below to find and compare flights from Tallahassee to Caribbean Islands that are best for you.

Fly from

Tallahassee

Fly to

Caribbean Islands

Route

Depart

Return

Price

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 2/18

3:24 pm-9:00 pm

1 stop4h 36m

San Juan Luis Munoz Marin Intl

Tue 2/24

2:45 pm-7:14 pm

1 stop5h 29m

$365

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 2/24

5:10 pm-11:49 pm

1 stop5h 39m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:15 am-12:09 pm

1 stop6h 54m

$365

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sat 2/7

6:00 am-5:01 pm

1 stop10h 01m

San Juan Luis Munoz Marin Intl

Sat 2/7

7:12 pm-9:16 am

1 stop15h 04m

$410

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 11/4

6:05 am-3:47 pm

2 stops8h 42m

San Juan Luis Munoz Marin Intl

Mon 11/17

2:47 pm-11:59 pm

1 stop10h 12m

$455

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Fri 11/14

8:40 pm-10:17 am

1 stop12h 37m

San Juan Luis Munoz Marin Intl

Mon 11/17

11:13 am-11:59 pm

1 stop13h 46m

$460

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 3/3

6:23 pm-9:36 am

2 stops14h 13m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:50 pm-1:15 pm

2 stops19h 25m

$468

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Thu 4/9

7:30 am-1:30 pm

1 stop6h 00m

Nassau Intl

Tue 4/14

3:03 pm-10:20 pm

1 stop7h 17m

$472

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 2/24

6:43 am-3:45 pm

2 stops8h 02m

San Juan Luis Munoz Marin Intl

Thu 2/26

4:50 pm-12:24 am

1 stop8h 34m

$473

TallahasseeNassau

TLH - NAS

TLHNAS

Tallahassee

Thu 4/9

6:28 am-11:20 am

1 stop4h 52m

Nassau Intl

Tue 4/14

1:10 pm-11:59 pm

2 stops10h 49m

$476

TallahasseePunta Cana

TLH - PUJ

TLHPUJ

Tallahassee

Sun 4/5

7:15 pm-12:25 pm

2 stops17h 10m

Punta Cana

Tue 4/7

5:05 pm-9:22 am

1 stop16h 17m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 32 results
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Best time to book a flight from Tallahassee to Caribbean Islands

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

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

Currently, April is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $232). Flying from Tallahassee to Caribbean Islands in December is currently the most expensive (average of $397). 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 EPX?

Find hourly flight availability from Tallahassee to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

It’s optimal to fly from Tallahassee to Caribbean Islands at noon. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight in the afternoon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated October 14, 2025.
Get a feel of what it's like to fly with American Airlines and Silver Airways from Tallahassee to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,040 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
Silver Airways
5.8
Fair
240 reviews
American Airlines
7.2
Good
11,040 reviews

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Tallahassee to Caribbean Islands. 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 Islands?

    Tallahassee (TLH), located 5.0 mi from the city center, is the airport you fly out of when you book flights from Tallahassee to Caribbean Islands.

  • How long is the flight from Tallahassee to Caribbean Islands?

    There are many flights that can get you from Tallahassee to Caribbean Islands in 4h 36m. Fly via American Airlines or Delta to get the fastest option. The distance from Tallahassee to Caribbean Islands is about 1415 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    When deciding which route to take from Tallahassee to Caribbean Islands 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 Islands that include hotel bookings?

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $232). Flying from Tallahassee to Caribbean Islands in December is currently the most expensive (average of $397). 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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Top 2 airlines flying from Tallahassee to Caribbean Islands

Discover the top 2 airlines that operate flights from Tallahassee to Caribbean Islands. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$456FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$607FlexibilityNo cancel feeOn-time71%

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