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Caribbean Islands

$294+ 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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
TLH — SJU
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
1 adult, Economy
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Cheap 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 May 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:07 pm
TLH
-
SJU
1 stop10h 31m
Multiple Airlines
Mon 10/55:12 pm
SJU
-
TLH
1 stop17h 18m
Multiple Airlines
Deal found 5/26$383
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:17 pm
TLH
-
SJU
1 stop25h 48m
Multiple Airlines
Sun 8/165:45 pm
SJU
-
TLH
2 stops39h 13m
Multiple Airlines
Deal found 5/27$384
This Delta deal was found by Cheapflights users on 5/26. 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.
Mon 8/176:00 am
TLH
-
MBJ
1 stop6h 44m
Delta
Wed 8/191:09 pm
MBJ
-
TLH
1 stop6h 00m
Delta
Deal found 5/26$422
This American Airlines deal was found by Cheapflights users on 5/27. 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 7/197:50 pm
TLH
-
MBJ
2 stops18h 19m
American Airlines
Wed 7/225:14 pm
MBJ
-
TLH
2 stops17h 20m
American Airlines
Deal found 5/27$427
This American Airlines deal was found by Cheapflights users on 5/26. 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 9/217:25 am
TLH
-
MBJ
1 stop6h 44m
American Airlines
Fri 9/2512:05 pm
MBJ
-
TLH
1 stop23h 50m
American Airlines
Deal found 5/26$430
This American Airlines deal was found by Cheapflights users on 5/26. 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 8/276:28 pm
TLH
-
MBJ
2 stops18h 14m
American Airlines
Mon 8/315:08 pm
MBJ
-
TLH
1 stop21h 51m
American Airlines
Deal found 5/26$435
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:08 am
TLH
-
SJU
1 stop8h 26m
Multiple Airlines
Sat 8/293:06 am
SJU
-
TLH
2 stops9h 01m
Multiple Airlines
Deal found 5/27$441
This American Airlines deal was found by Cheapflights users on 5/23. 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.
Sat 8/157:47 pm
TLH
-
SJU
2 stops13h 56m
American Airlines
Tue 8/1810:33 am
SJU
-
TLH
1 stop7h 50m
American Airlines
Deal found 5/23$446
This American Airlines deal was found by Cheapflights users on 5/27. 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 11/186:00 am
TLH
-
SJU
1 stop15h 39m
American Airlines
Tue 11/246:00 am
SJU
-
TLH
1 stop10h 39m
American Airlines
Deal found 5/27$451
This Kiwi.com deal was found by Cheapflights users on 5/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:08 am
TLH
-
SJU
2 stops15h 21m
Multiple Airlines
Mon 7/66:00 am
SJU
-
TLH
1 stop26h 58m
Multiple Airlines
Deal found 5/23$495
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:17 pm
TLH
-
NAS
1 stop4h 58m
Multiple Airlines
Wed 8/124:00 pm
NAS
-
TLH
1 stop15h 28m
Multiple Airlines
Deal found 5/24$504
This American Airlines deal was found by Cheapflights users on 5/23. 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.
Sat 6/137:43 pm
TLH
-
SJU
2 stops13h 56m
American Airlines
Tue 6/237:16 pm
SJU
-
TLH
1 stop13h 46m
American Airlines
Deal found 5/23$506

Find 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 May 28, 2026.

Round-trip from

$383
(Kiwi.com)

One-way from

$294
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$606
From Tallahassee to Caribbean Islands
Search Deals
One-way flight from Tallahassee to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 28, 2026.
Use the filters below to find and compare flights from Tallahassee to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Thu 10/1

1:07 pm-11:38 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Mon 10/5

6:15 am-10:30 am

2 stops28h 15m

$403

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Mon 8/17

6:00 am-11:44 am

1 stop6h 44m

Montego Bay Sangster Intl

Wed 8/19

1:09 pm-8:09 pm

1 stop6h 00m

$422

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Sun 7/19

6:00 am-1:09 pm

1 stop8h 09m

Montego Bay Sangster Intl

Wed 7/22

5:14 pm-11:34 am

2 stops17h 20m

$427

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Mon 9/21

7:25 am-1:09 pm

1 stop6h 44m

Montego Bay Sangster Intl

Fri 9/25

5:16 pm-10:27 am

2 stops16h 11m

$427

TallahasseeMontego Bay

TLH - MBJ

TLHMBJ

Tallahassee

Thu 8/27

6:28 pm-11:42 am

2 stops18h 14m

Montego Bay Sangster Intl

Mon 8/31

5:08 pm-3:59 pm

1 stop21h 51m

$435

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 10/20

1:00 pm-9:59 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Tue 10/27

2:31 pm-8:46 pm

1 stop6h 15m

$446

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Tue 8/11

6:05 am-4:03 pm

1 stop9h 58m

San Juan Luis Munoz Marin Intl

Sun 8/16

10:33 am-11:59 pm

1 stop13h 26m

$446

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sat 10/24

8:28 pm-11:05 am

1 stop14h 37m

San Juan Luis Munoz Marin Intl

Tue 10/27

8:35 am-2:49 pm

1 stop6h 14m

$446

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Thu 8/27

8:17 pm-9:43 am

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Sun 8/30

10:33 am-11:59 pm

1 stop13h 26m

$446

TallahasseeSan Juan

TLH - SJU

TLHSJU

Tallahassee

Sat 6/13

8:18 pm-9:39 am

1 stop13h 21m

San Juan Luis Munoz Marin Intl

Tue 6/23

7:16 pm-9:02 am

1 stop13h 46m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 35 resultsSorted by cheapest first
1
2
3
4

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, May is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $356). Flying from Tallahassee to Caribbean Islands in October is currently the most expensive (average of $661). 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 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 May 28, 2026.
Get a feel of what it's like to fly with American Airlines 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
7.1
Good
11,639 reviews

Comfort

7.2

Boarding

7.5

Crew

7.9

Entertainment

6.9

Food

6.4

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,639 reviews
American Airlines
7.1
Good
11,639 reviews

Comfort

7.2

Boarding

7.5

Crew

7.9

Entertainment

6.9

Food

6.4

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 6h 44m. Fly via Delta or American Airlines to get the fastest option. The distance from Tallahassee to Caribbean Islands is about 915 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 - Nassau Intl or Tallahassee - Punta Cana 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, May is the cheapest month in which you can book a flight from Tallahassee to Caribbean Islands (average of $356). Flying from Tallahassee to Caribbean Islands in October is currently the most expensive (average of $661). 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 May 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$247Average$661FlexibilityNo cancel feeOn-time71%
DeltaCheapest$252Average$615FlexibilityNo cancel feeOn-timeN/A

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