$288 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 4/24. 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$561
Nassau
Nassau1 stop$521
Saint Thomas Island
Saint Thomas Island1 stop$500
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$610
Bridgetown
Bridgetown2 stops$622
George Town
George Town1 stop$571
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$521
Saint Thomas Island
Saint Thomas Island1 stop$500
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$610
Bridgetown
Bridgetown2 stops$622
George Town
George Town1 stop$571

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

Mon, Apr 6 - Wed, Apr 8
American Airlines Logo
7:55 pm - 12:03 pm
TLH
-
SJU
16h 08m
1 stop
American Airlines Logo
11:59 pm - 1:01 pm
SJU
-
TLH
13h 02m
1 stop
$386American Airlines
Wed, Apr 8 - Sat, Apr 11
American Airlines Logo
8:15 am - 11:01 pm
TLH
-
SJU
14h 46m
1 stop
American Airlines Logo
10:01 am - 11:56 pm
SJU
-
TLH
13h 55m
1 stop
$411American Airlines
Tue, Mar 10 - Thu, Mar 19
American Airlines Logo
11:13 am - 3:25 pm
TLH
-
ELH
4h 12m
1 stop
American Airlines Logo
2:02 pm - 12:24 am
ELH
-
TLH
10h 22m
1 stop
$424American Airlines
Sun, Feb 15 - Thu, Feb 26
Delta Logo
5:23 pm - 11:58 pm
TLH
-
SJU
5h 35m
1 stop
Delta Logo
7:30 am - 12:43 pm
SJU
-
TLH
6h 13m
1 stop
$426Delta
Tue, Mar 10 - Thu, Mar 19
American Airlines Logo
7:01 pm - 3:25 pm
TLH
-
ELH
20h 24m
2 stops
American Airlines Logo
2:02 pm - 12:24 am
ELH
-
TLH
10h 22m
1 stop
$429American Airlines
Sat, Mar 21 - Mon, Mar 30
American Airlines Logo
7:55 pm - 10:40 am
TLH
-
SJU
14h 45m
1 stop
American Airlines Logo
6:00 am - 8:21 pm
SJU
-
TLH
14h 21m
1 stop
$436American Airlines
Wed, May 6 - Sun, May 10
Delta Logo
7:10 am - 1:16 pm
TLH
-
MBJ
7h 06m
1 stop
Delta Logo
12:55 pm - 10:20 pm
MBJ
-
TLH
8h 25m
1 stop
$561Delta
Wed, May 6 - Sun, May 10
Delta Logo
7:10 am - 3:29 pm
TLH
-
MBJ
9h 19m
1 stop
Delta Logo
12:55 pm - 8:46 pm
MBJ
-
TLH
6h 51m
1 stop
$577Delta
Sun, Feb 15 - Wed, Feb 18
WestJet Logo
5:23 pm - 3:40 pm
TLH
-
NAS
22h 17m
2 stops
WestJet Logo
6:15 pm - 6:40 pm
NAS
-
TLH
24h 25m
2 stops
$1,518WestJet
Sun, Feb 15 - Wed, Feb 18
WestJet Logo
1:28 pm - 3:40 pm
TLH
-
NAS
26h 12m
2 stops
WestJet Logo
6:15 pm - 6:40 pm
NAS
-
TLH
24h 25m
2 stops
$1,521WestJet
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 $453, 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 February, when tickets cost $413 (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 seasonFebruary
Cheapest flight$288
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Tallahassee to Saint Thomas Island

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 11153 reviews
8.0Crew
6.4Food
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

Little warm on the plane and delayed for an hour

8.0 ExcellentHoward, Jan 2026
FLL - ORD
Read more American Airlines reviews

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.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Tallahassee (TLH)