$243 Find Cheap Flights from Tallahassee to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Caribbean Islands departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tallahassee to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Tallahassee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$542
Nassau
Nassau1 stop$468
Saint Thomas Island
Saint Thomas Island2 stops$500
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$540
Bridgetown
Bridgetown1 stop$587
George Town
George Town1 stop$546
Willemstad
Willemstad2 stops$568
St. John's
St. John's2 stops$581
Montego Bay
Montego Bay1 stop$542
Nassau
Nassau1 stop$468
Saint Thomas Island
Saint Thomas Island2 stops$500
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$540
Bridgetown
Bridgetown1 stop$587
George Town
George Town1 stop$546
Willemstad
Willemstad2 stops$568
St. John's
St. John's2 stops$581

Book Cheap Tallahassee to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tallahassee to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Caribbean Islands

Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
7:54 pm - 10:48 am
TLH
-
SJU
14h 54m
1 stop
American Airlines Logo
1:31 pm - 10:41 pm
SJU
-
TLH
9h 10m
2 stops
$386American Airlines
Wed, Apr 8 - Sat, Apr 11
American Airlines Logo
8:15 pm - 9:13 am
TLH
-
SJU
12h 58m
1 stop
American Airlines Logo
11:43 am - 11:56 pm
SJU
-
TLH
12h 13m
1 stop
$411American Airlines
Mon, Apr 6 - Wed, Apr 8
American Airlines Logo
11:13 am - 5:11 pm
TLH
-
SJU
5h 58m
1 stop
American Airlines Logo
11:59 pm - 1:02 pm
SJU
-
TLH
13h 03m
1 stop
$426American Airlines
Sun, Mar 1 - Wed, Mar 4
American Airlines Logo
6:04 am - 1:33 pm
TLH
-
SJU
6h 29m
1 stop
American Airlines Logo
8:00 am - 8:18 pm
SJU
-
TLH
13h 18m
1 stop
$446American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
8:51 pm - 10:56 am
TLH
-
SJU
14h 05m
1 stop
American Airlines Logo
11:43 am - 11:56 pm
SJU
-
TLH
12h 13m
1 stop
$451American Airlines
Mon, Jul 27 - Fri, Jul 31
Delta Logo
7:30 am - 3:54 pm
TLH
-
NAS
8h 24m
1 stop
Delta Logo
5:20 pm - 10:20 pm
NAS
-
TLH
5h 00m
1 stop
$468Delta
Mon, Jul 27 - Fri, Jul 31
American Airlines Logo
7:47 pm - 9:29 am
TLH
-
NAS
13h 42m
2 stops
American Airlines Logo
4:04 pm - 11:59 pm
NAS
-
TLH
7h 55m
1 stop
$472American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
8:51 pm - 9:00 am
TLH
-
SJU
12h 09m
1 stop
American Airlines Logo
6:01 pm - 11:56 pm
SJU
-
TLH
5h 55m
1 stop
$491American Airlines
Wed, Apr 22 - Tue, May 5
American Airlines Logo
5:33 pm - 1:15 pm
TLH
-
STT
19h 42m
2 stops
American Airlines Logo
5:05 pm - 1:02 pm
STT
-
TLH
19h 57m
2 stops
$500American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:23 am - 1:33 pm
TLH
-
NAS
6h 10m
1 stop
Delta Logo
2:59 pm - 7:34 pm
NAS
-
TLH
4h 35m
1 stop
$526Delta
Booking Insights

KAYAK's insights & trends for Tallahassee to Caribbean Islands flights

Get data-powered insights and trends into flights from Tallahassee to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Tallahassee to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $423, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Tallahassee to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tallahassee to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Tallahassee to Caribbean Islands is September, when tickets cost $458 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $690 and $680 respectively.

Find deals

Good to know

Low seasonNovember
Cheapest flight$243
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Tallahassee to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Tallahassee to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tallahassee to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tallahassee to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Tallahassee to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tallahassee to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Tallahassee to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tallahassee to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Tallahassee to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Tallahassee to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tallahassee to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11222 reviews
8.0Crew
6.9Entertainment
6.4Food
7.5Boarding
7.2Comfort
Airline reviews

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

2.0 MediocreSalim, Feb 2026
JAX - PHL
Read more American Airlines reviews

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Tallahassee (TLH)