$303 Find Cheap Flights from Tallahassee to Caribbean - Compare and Save

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 departing on 6/27. 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

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Cheap Flights from Tallahassee to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$437
Nassau
Nassau1 stop$429
Simpson Bay
Simpson Bay1 stop$659
Providenciales
Providenciales1 stop$645
Bridgetown
Bridgetown2 stops$3,713
Willemstad
Willemstad2 stops$774
St. John's
St. John's1 stop$790
Montego Bay
Montego Bay1 stop$437
Nassau
Nassau1 stop$429
Simpson Bay
Simpson Bay1 stop$659
Providenciales
Providenciales1 stop$645
Bridgetown
Bridgetown2 stops$3,713
Willemstad
Willemstad2 stops$774
St. John's
St. John's1 stop$790

Book Cheap Tallahassee to Caribbean 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 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

Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
1:07 pm - 11:38 pm
TLH
-
SJU
10h 31m
1 stop
Multiple Airlines Logo
5:12 pm - 10:30 am
SJU
-
TLH
17h 18m
1 stop
$342Multiple Airlines
Thu, Jul 30 - Wed, Aug 5
Multiple Airlines Logo
12:47 pm - 2:00 pm
TLH
-
SJU
49h 13m
2 stops
Multiple Airlines Logo
6:00 am - 7:28 am
SJU
-
TLH
25h 28m
1 stop
$375Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
1:07 pm - 11:38 pm
TLH
-
SJU
10h 31m
1 stop
Multiple Airlines Logo
4:30 pm - 3:12 pm
SJU
-
TLH
22h 42m
2 stops
$401Multiple Airlines
Wed, Sep 30 - Thu, Oct 8
American Airlines Logo
4:24 pm - 12:51 pm
TLH
-
STT
20h 27m
2 stops
American Airlines Logo
5:40 pm - 9:54 am
STT
-
TLH
16h 14m
1 stop
$403American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
9:32 am - 4:00 pm
TLH
-
STT
6h 28m
1 stop
American Airlines Logo
4:50 pm - 12:55 pm
STT
-
TLH
20h 05m
2 stops
$433American Airlines
Sun, Jul 19 - Wed, Jul 22
American Airlines Logo
6:00 am - 1:09 pm
TLH
-
MBJ
8h 09m
1 stop
American Airlines Logo
5:14 pm - 1:11 pm
MBJ
-
TLH
18h 57m
2 stops
$437American Airlines
Fri, Sep 18 - Mon, Sep 21
American Airlines Logo
2:07 pm - 8:47 pm
TLH
-
SJU
6h 40m
1 stop
American Airlines Logo
10:16 am - 11:38 pm
SJU
-
TLH
13h 22m
1 stop
$446American Airlines
Sun, Sep 13 - Fri, Sep 18
Delta Logo
5:35 am - 11:50 am
TLH
-
NAS
6h 15m
1 stop
Delta Logo
1:15 pm - 6:19 pm
NAS
-
TLH
5h 04m
1 stop
$536Delta
Sun, Sep 13 - Thu, Sep 17
Delta Logo
3:40 pm - 11:30 am
TLH
-
NAS
19h 50m
2 stops
Delta Logo
1:15 pm - 6:19 pm
NAS
-
TLH
5h 04m
1 stop
$540Delta
Mon, Sep 14 - Tue, Sep 15
Delta Logo
6:10 am - 11:50 am
TLH
-
NAS
5h 40m
1 stop
Delta Logo
12:55 pm - 11:14 am
NAS
-
TLH
22h 19m
2 stops
$570Delta
Booking Insights

KAYAK's insights & trends for Tallahassee to Caribbean flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tallahassee to Caribbean, 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 is May, when tickets cost $356 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $621 and $581 respectively.

Good to know

Low seasonFebruary
Cheapest flight$303
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Tallahassee to San Juan

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Tallahassee to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Tallahassee to Caribbean

 
Need help choosing which airline to fly with from Tallahassee to Caribbean? 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.
7.9
DeltaOverall score based on 8396 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

8.0 ExcellentAnonymous, Jun 2026
TPA - LGA
Read more Delta reviews

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports