$259 Find Cheap Flights from Tallahassee to Caribbean - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Caribbean departing on 9/24. 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.
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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 Bay2 stops$467
Nassau
Nassau1 stop$587
Simpson Bay
Simpson Bay1 stop$697
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown1 stop$842
George Town
George Town1 stop$651
Willemstad
Willemstad1 stop$649
Montego Bay
Montego Bay2 stops$467
Nassau
Nassau1 stop$587
Simpson Bay
Simpson Bay1 stop$697
Providenciales
Providenciales1 stop$650
Bridgetown
Bridgetown1 stop$842
George Town
George Town1 stop$651
Willemstad
Willemstad1 stop$649

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 - 1:34 pm
TLH
-
SJU
24h 27m
1 stop
Multiple Airlines Logo
7:00 am - 10:30 am
SJU
-
TLH
27h 30m
1 stop
$259Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
1:07 pm - 1:34 pm
TLH
-
SJU
24h 27m
1 stop
Multiple Airlines Logo
7:00 am - 10:30 am
SJU
-
TLH
27h 30m
1 stop
$267Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
1:07 pm - 1:34 pm
TLH
-
SJU
24h 27m
1 stop
Multiple Airlines Logo
7:00 am - 10:30 am
SJU
-
TLH
27h 30m
1 stop
$271Multiple Airlines
Thu, Sep 24 - Thu, Oct 8
Multiple Airlines Logo
1:07 pm - 1:34 pm
TLH
-
SJU
24h 27m
1 stop
Multiple Airlines Logo
5:12 pm - 9:30 am
SJU
-
TLH
16h 18m
1 stop
$284Multiple Airlines
Sat, Nov 7 - Mon, Nov 16
American Airlines Logo
6:44 pm - 12:17 pm
TLH
-
STT
16h 33m
2 stops
American Airlines Logo
3:15 pm - 10:21 am
STT
-
TLH
20h 06m
2 stops
$418American Airlines
Sat, Nov 7 - Mon, Nov 16
American Airlines Logo
8:23 pm - 12:17 pm
TLH
-
STT
14h 54m
1 stop
American Airlines Logo
1:07 pm - 5:51 pm
STT
-
TLH
5h 44m
1 stop
$418American Airlines
Sat, Nov 7 - Mon, Nov 16
American Airlines Logo
6:44 pm - 2:23 pm
TLH
-
STT
18h 39m
2 stops
American Airlines Logo
1:07 pm - 5:51 pm
STT
-
TLH
5h 44m
1 stop
$418American Airlines
Thu, Aug 27 - Thu, Sep 3
Delta Logo
6:00 am - 1:34 pm
TLH
-
STT
7h 34m
1 stop
Delta Logo
2:49 pm - 8:51 pm
STT
-
TLH
6h 02m
1 stop
$521Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
3:49 pm - 10:29 pm
TLH
-
SJU
6h 40m
1 stop
Delta Logo
2:59 pm - 11:03 pm
SJU
-
TLH
8h 04m
1 stop
$596Delta
Wed, Aug 19 - Tue, Aug 25
Delta Logo
6:00 am - 11:39 am
TLH
-
GCM
6h 39m
1 stop
Delta Logo
1:04 pm - 8:09 pm
GCM
-
TLH
6h 05m
1 stop
$681Delta
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 September, when tickets cost $523 (return) on average. On the other hand, the most expensive months are October and May, when the average cost of round-trip tickets is $749 and $734 respectively.

Good to know

Low season

October

Cheapest flight

$259
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly and prices are also 2% 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.
7.8
DeltaOverall score based on 8487 reviews
8.1Boarding
7.2Food
7.8Comfort
8.5Crew
7.8Entertainment
Airline reviews

Boarding was quick and i made my connection early due to early arrival time

10.0 ExcellentKalen, Jul 2026
TPA - ATL
Read more Delta reviews

Boarding was quick and i made my connection early due to early arrival time

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

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.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

I left my wallet on flight 2225, no one has reached out to me yet, I field out the form online. Please give me a call Please.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports