$190 Find Cheap Flights from Tallahassee to Caribbean Islands - 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 Islands departing on 8/4. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
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 Bay2 stops$496
Nassau
Nassau1 stop$597
Simpson Bay
Simpson Bay1 stop$757
Providenciales
Providenciales1 stop$660
Bridgetown
Bridgetown1 stop$710
Willemstad
Willemstad2 stops$636
Montego Bay
Montego Bay2 stops$496
Nassau
Nassau1 stop$597
Simpson Bay
Simpson Bay1 stop$757
Providenciales
Providenciales1 stop$660
Bridgetown
Bridgetown1 stop$710
Willemstad
Willemstad2 stops$636

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

Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
1:07 pm - 11:38 pm
TLH
-
SJU
10h 31m
1 stop
Multiple Airlines Logo
5:12 pm - 9:30 am
SJU
-
TLH
16h 18m
1 stop
$280Multiple Airlines
Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
8:25 am - 11:57 pm
TLH
-
SJU
15h 32m
2 stops
Multiple Airlines Logo
5:12 pm - 9:30 am
SJU
-
TLH
16h 18m
1 stop
$306Multiple Airlines
Tue, Aug 25 - Sat, Aug 29
Multiple Airlines Logo
9:38 am - 7:52 pm
TLH
-
SJU
10h 14m
2 stops
Multiple Airlines Logo
6:35 am - 7:28 am
SJU
-
TLH
24h 53m
1 stop
$322Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
8:08 am - 12:07 am
TLH
-
SJU
15h 59m
1 stop
Multiple Airlines Logo
10:48 pm - 1:37 pm
SJU
-
TLH
14h 49m
2 stops
$336Multiple Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
6:05 am - 12:53 pm
TLH
-
STT
6h 48m
1 stop
American Airlines Logo
1:49 pm - 10:27 am
STT
-
TLH
20h 38m
2 stops
$434American Airlines
Wed, Sep 16 - Sun, Sep 20
American Airlines Logo
10:56 am - 12:51 pm
TLH
-
STT
25h 55m
2 stops
American Airlines Logo
1:41 pm - 12:55 pm
STT
-
TLH
23h 14m
2 stops
$458American Airlines
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:00 am - 1:30 pm
TLH
-
GGT
7h 30m
1 stop
Delta Logo
2:25 pm - 11:03 pm
GGT
-
TLH
8h 38m
1 stop
$649Delta
Sat, Jan 9 - Tue, Jan 12
Delta Logo
5:35 am - 2:25 pm
TLH
-
PLS
8h 50m
1 stop
Delta Logo
2:15 pm - 10:20 pm
PLS
-
TLH
8h 05m
1 stop
$660Delta
Sat, Oct 24 - Tue, Oct 27
WestJet Logo
12:00 pm - 2:35 pm
TLH
-
PUJ
50h 35m
2 stops
WestJet Logo
3:30 pm - 4:25 pm
PUJ
-
TLH
24h 55m
2 stops
$3,558WestJet
Sat, Oct 24 - Tue, Oct 27
WestJet Logo
12:00 pm - 2:35 pm
TLH
-
PUJ
50h 35m
2 stops
WestJet Logo
3:30 pm - 4:25 pm
PUJ
-
TLH
24h 55m
2 stops
$3,563WestJet
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 $477, 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 $529 (return) on average. On the other hand, the most expensive months are October and November, when the average cost of round-trip tickets is $859 and $817 respectively.

Good to know

Low season

October

Cheapest flight

$190
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 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.
7.1
American AirlinesOverall score based on 11826 reviews
6.8Entertainment
7.5Boarding
6.4Food
7.2Comfort
7.9Crew
Airline reviews

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.

4.0 OkayHARMONY, Jul 2026
MCO - DFW
Read more American Airlines reviews

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.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

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 Islands

Information on your arrival and departure airports