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Caribbean Islands

$187+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$406
(Trip.com)

One-way from

$187
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$390
From Tallahassee to Caribbean Islands
Search Deals
One-way flight from Tallahassee to Caribbean Islands
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Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Trip.com deal was found by Cheapflights users on 4/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:45 pmTLH - STT
1 stop14h 12mMultiple Airlines
Tue 6/310:52 amSTT - TLH
1 stop8h 13mMultiple Airlines
Deal found 4/23$424
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 5/275:54 pmTLH - STT
2 stops20h 54mAmerican Airlines
Tue 6/35:10 pmSTT - TLH
2 stops18h 27mAmerican Airlines
Deal found 4/23$459
This American Airlines deal was found by Cheapflights users on 4/22. 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 6/258:46 pmTLH - SJU
1 stop14h 19mAmerican Airlines
Wed 7/23:45 pmSJU - TLH
1 stop6h 49mAmerican Airlines
Deal found 4/22$460
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 7/156:00 amTLH - MBJ
1 stop8h 25mAmerican Airlines
Tue 7/2210:20 amMBJ - TLH
1 stop8h 59mAmerican Airlines
Deal found 4/23$513
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sun 4/278:39 pmTLH - NAS
1 stop12h 48mAmerican Airlines
Wed 4/302:43 pmNAS - TLH
1 stop9h 19mAmerican Airlines
Deal found 4/23$519
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:00 pmTLH - SJU
1 stop9h 12mDelta
Mon 8/46:15 amSJU - TLH
1 stop8h 27mDelta
Deal found 4/23$530
This JetBlue deal was found by Cheapflights users on 4/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/59:05 amTLH - SJU
1 stop7h 10mJetBlue
Mon 6/911:55 amSJU - TLH
1 stop7h 10mJetBlue
Deal found 4/22$650
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/257:45 pmTLH - SJU
2 stops18h 00mUnited Airlines
Tue 7/12:05 amSJU - TLH
2 stops17h 00mUnited Airlines
Deal found 4/22$692
This JetBlue deal was found by Cheapflights users on 4/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/279:05 amTLH - NAS
1 stop6h 41mJetBlue
Tue 4/2911:54 amNAS - TLH
1 stop7h 11mJetBlue
Deal found 4/23$703
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/275:38 amTLH - NAS
2 stops9h 12mDelta
Tue 4/293:09 pmNAS - TLH
1 stop5h 40mDelta
Deal found 4/23$769
This American Airlines deal was found by Cheapflights users on 4/22. 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 4/258:09 pmTLH - PLS
1 stop14h 06mAmerican Airlines
Mon 4/2811:15 amPLS - TLH
1 stop12h 47mAmerican Airlines
Deal found 4/22$794
This Delta deal was found by Cheapflights users on 4/22. 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 4/255:38 amTLH - PLS
2 stops9h 12mDelta
Mon 4/282:05 pmPLS - TLH
1 stop6h 44mDelta
Deal found 4/22$798

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 April 24, 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

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Tue 5/27

7:45 pm-9:57 am

1 stop14h 12m

Saint Thomas Island Cyril E King

Tue 6/3

10:52 am-7:05 pm

1 stop8h 13m

$424

TallahasseeSaint Thomas Island

TLH - STT

TLHSTT

Tallahassee

Tue 5/27

5:54 pm-2:48 pm

2 stops20h 54m

Saint Thomas Island Cyril E King

Tue 6/3

5:10 pm-11:37 am

2 stops18h 27m

$459

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 6/25

8:46 pm-11:05 am

1 stop14h 19m

San Juan Luis Munoz Marin Intl

Wed 7/2

3:45 pm-10:34 pm

1 stop6h 49m

$460

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Tue 7/15

6:00 am-1:25 pm

1 stop8h 25m

Montego Bay Sangster Intl

Tue 7/22

10:20 am-8:19 pm

1 stop8h 59m

$513

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Thu 7/31

1:00 pm-10:12 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

Mon 8/4

6:15 am-2:42 pm

1 stop8h 27m

$530

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Thu 6/5

9:05 am-4:15 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Mon 6/9

11:55 am-7:05 pm

1 stop7h 10m

$650

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 6/25

7:45 pm-1:45 pm

2 stops18h 00m

San Juan Luis Munoz Marin Intl

Tue 7/1

2:05 am-7:05 pm

2 stops17h 00m

$692

TallahasseeCastries

TLH - UVF

TLHUVF

Tallahassee

Fri 6/27

2:21 pm-1:45 pm

2 stops23h 24m

Castries Hewanorra

Sat 7/5

3:15 pm-1:50 pm

2 stops22h 35m

$833

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sat 5/17

9:05 am-7:07 pm

1 stop10h 02m

$187

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Wed 4/30

9:05 am-4:40 pm

1 stop7h 35m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 13 results
1
2

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, September is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $254). Flying from Tallahassee to Caribbean Islands in December is currently the most expensive (average of $336). 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 April 24, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Tallahassee to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
JetBlue
7.3
Good
2,924 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Silver Airways
6.0
Okay
251 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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.

  • What are the cheapest airlines to fly from Tallahassee to Caribbean Islands one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $220. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Tallahassee to Caribbean Islands for a low price.

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

    When deciding which route to take from Tallahassee to Caribbean Islands consider Tallahassee - Montego Bay Sangster Intl, Tallahassee - Saint Thomas Island Cyril E King or Tallahassee - San Juan Luis Munoz Marin Intl 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, September is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $254). Flying from Tallahassee to Caribbean Islands in December is currently the most expensive (average of $336). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Tallahassee to Caribbean Islands

Discover the top 3 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$334Average$577FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$388Average$606FlexibilityNo cancel feeOn-time62%

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