$360 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 12/23. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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 Bay1 stop$531
Nassau
Nassau1 stop$475
Bridgetown
Bridgetown1 stop$621
George Town
George Town1 stop$590
Willemstad
Willemstad1 stop$562
Montego Bay
Montego Bay1 stop$531
Nassau
Nassau1 stop$475
Bridgetown
Bridgetown1 stop$621
George Town
George Town1 stop$590
Willemstad
Willemstad1 stop$562

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

Tue, Feb 24 - Thu, Feb 26
Delta Logo
5:35 am - 1:00 pmTLH-SJU
6h 25m1 stop
Delta Logo
7:30 am - 2:46 pmSJU-TLH
8h 16m1 stop
$365Delta
Find Deal
Tue, Feb 24 - Thu, Feb 26
American Airlines Logo
6:43 am - 5:05 pmTLH-SJU
9h 22m2 stops
American Airlines Logo
8:04 am - 5:28 pmSJU-TLH
10h 24m1 stop
$473American Airlines
Find Deal
Sun, Nov 9 - Tue, Nov 18
Delta Logo
5:35 am - 11:54 amTLH-NAS
6h 19m1 stop
Delta Logo
2:55 pm - 10:18 pmNAS-TLH
7h 23m1 stop
$475Delta
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
9:59 am - 2:06 pmTLH-NAS
4h 07m1 stop
American Airlines Logo
3:17 pm - 11:32 pmNAS-TLH
8h 15m2 stops
$479American Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16
American Airlines Logo
7:08 pm - 4:57 pmTLH-STT
20h 49m2 stops
American Airlines Logo
6:17 pm - 9:29 amSTT-TLH
16h 12m1 stop
$479American Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
American Airlines Logo
3:34 pm - 10:43 amTLH-NAS
19h 09m2 stops
American Airlines Logo
10:33 am - 6:43 pmNAS-TLH
8h 10m2 stops
$494American Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
WestJet Logo
7:00 am - 3:50 pmTLH-NAS
32h 50m2 stops
WestJet Logo
4:50 pm - 6:31 pmNAS-TLH
25h 41m2 stops
$940WestJet
Find Deal
Mon, Nov 10 - Mon, Nov 17
WestJet Logo
7:08 pm - 3:50 pmTLH-NAS
20h 42m2 stops
WestJet Logo
4:50 pm - 11:34 amNAS-TLH
18h 44m2 stops
$941WestJet
Find Deal
Fri, Jan 16 - Mon, Jan 19
LATAM Airlines Logo
2:10 pm - 11:40 amTLH-PUJ
20h 30m2 stops
LATAM Airlines Logo
2:45 am - 10:22 pmPUJ-TLH
20h 37m2 stops
$1,857LATAM Airlines
Find Deal
Tue, Sep 30 - Thu, Oct 2
LATAM Airlines Logo
5:12 pm - 5:35 pmTLH-PUJ
24h 23m2 stops
LATAM Airlines Logo
2:45 am - 10:32 amPUJ-TLH
31h 47m2 stops
$2,283LATAM Airlines
Find Deal
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 $390, 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 January, when tickets cost $390 (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 $675 respectively.

What’s the cheapest day of the week to fly from Tallahassee to Caribbean Islands?

The average price of all round-trip flights from Tallahassee to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Tallahassee to Caribbean Islands, look for departures on Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Caribbean Islands, Wednesday is the cheapest day to fly and Friday is the most expensive.

How far in advance should I book a flight from Tallahassee to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Tallahassee to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$360
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 4% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $443 on average. Morning departures are around 7% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $540.

Reviews of the top airlines 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 10000 reviews
6.4Food
6.9Entertainment
7.2Comfort
8.0Crew
7.5Boarding
Airline reviews

Lost bag and 2 days no word leaving for cruise no clothes or stuff

2.0 MediocreYvonne, Sep 2025PBI - ORD
Read more American Airlines reviews

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

TERRIBLE. Cancelled my flight one month before my trip. Have not received my refund back.

Airline is in bankrupt and they didn't communicate it to customers

The outgoing flight tpa to fll was seriously delayed due to a frontal system impacting the incoming flight from key west. Weather is not under the control of the airline, better to arrive late than never! Thank you Silver Airways for your caution.

They canceled the flight and no longer fly out of Orlando. Trying to get my money refunded. Lost a night I paid for in Key West.

There was no serving off food on the flight being that it was so short.

The flight was VERY, VERY hot and the blowers weren't cooling it off...don't know what the problem was, but.....otherwise it was fine.

My flight from Avianca was 45 minutes late and it's very complicated to recheck in in ...also I have to say the silver desk folks were neither efficient nor helpful...so I missed my connecting flight. I actually got there before tge flight left but they refused to let me on....and gave me no vouchers for hotel etc

The cancelled our flight 3 times and we never made it to our destination. Every single airplane had a maintenance problem. Never fly this airline

9 hrs wait in airport then flt redirected to airport an hour away from our booked airport. Then at 8:00pm flight Cancelled. Silver supposed to book us on American the next day. Booked my husband but not me. Cost me Ubers, hotel, meals, new ticket and 1 hour taxi Cuz no flights to our home airport. Absolute disaster. Silver staff had no idea what was going on or what to do. Never Again Silver

Nothing about this flight was good. They are always cancelling or grossly delayed. We were delayed for 45 minutes for no apparent reason with no explanation or anything we could see and I missed my connection to Durham NC. I was on my way to my best friends memorial and funeral. Now I'll missed them both!!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.