$268 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 9/15. 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
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Best Caribbean Islands Flight Deals from Tallahassee

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$515
Nassau
Nassau1 stop$496
Simpson Bay
Simpson Bay1 stop$559
Providenciales
Providenciales1 stop$474
Bridgetown
Bridgetown1 stop$532
George Town
George Town1 stop$780
St. John's
St. John's2 stops$686
Montego Bay
Montego Bay1 stop$515
Nassau
Nassau1 stop$496
Simpson Bay
Simpson Bay1 stop$559
Providenciales
Providenciales1 stop$474
Bridgetown
Bridgetown1 stop$532
George Town
George Town1 stop$780
St. John's
St. John's2 stops$686

Cheap Flights from Tallahassee to Caribbean Islands

 
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

Wed, Dec 24 - Sat, Jan 10
American Airlines Logo
2:01 pm - 12:25 amTLH-SJU
9h 24m2 stops
American Airlines Logo
2:45 pm - 12:24 amSJU-TLH
10h 39m1 stop
$436American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
7:33 pm - 12:25 pmTLH-PLS
16h 52m1 stop
American Airlines Logo
1:30 pm - 8:10 pmPLS-TLH
6h 40m1 stop
$474American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
3:34 pm - 12:30 pmTLH-PLS
20h 56m2 stops
American Airlines Logo
1:25 pm - 9:31 pmPLS-TLH
8h 06m1 stop
$478American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
7:33 pm - 11:36 amTLH-PUJ
16h 03m2 stops
American Airlines Logo
4:30 pm - 3:06 pmPUJ-TLH
22h 36m1 stop
$483American Airlines
Find Deal
Mon, Jul 28 - Thu, Jul 31
American Airlines Logo
8:50 pm - 12:44 pmTLH-SJU
15h 54m1 stop
American Airlines Logo
7:00 pm - 12:22 amSJU-TLH
5h 22m1 stop
$485American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
1:32 pm - 3:45 pmTLH-PUJ
26h 13m1 stop
American Airlines Logo
4:30 pm - 3:06 pmPUJ-TLH
22h 36m1 stop
$486American Airlines
Find Deal
Wed, Sep 24 - Mon, Sep 29
Delta Logo
6:50 am - 1:50 pmTLH-SXM
7h 00m1 stop
Delta Logo
3:20 pm - 10:36 pmSXM-TLH
7h 16m1 stop
$562Delta
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Fri, Oct 10 - Mon, Oct 13
LATAM Airlines Logo
7:15 pm - 11:20 amTLH-PUJ
16h 05m2 stops
LATAM Airlines Logo
2:45 am - 9:23 amPUJ-TLH
30h 38m2 stops
$1,070LATAM Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
WestJet Logo
1:00 pm - 5:55 pmTLH-MBJ
52h 55m2 stops
WestJet Logo
2:55 pm - 6:47 pmMBJ-TLH
27h 52m2 stops
$1,625WestJet
Find Deal
Thu, Oct 9 - Sun, Oct 12
LATAM Airlines Logo
7:15 pm - 3:20 pmTLH-PUJ
20h 05m2 stops
LATAM Airlines Logo
2:45 am - 9:23 amPUJ-TLH
30h 38m2 stops
$2,290LATAM Airlines
Find Deal
Useful Info

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 $485, 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 $375 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $670 and $599 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.


Good to know

Low seasonAugust
High seasonDecember
Cheapest flight$268
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 5% lower on average.
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.

  • 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
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
6.5Food
Airline reviews

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

4.0 OkayAnonymous, Jun 2025MIA - GIG
Read more American Airlines reviews

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.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

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!!

Total disaster! The easiest flight was kept delayed till … cancelled! And before official announcement of the flight cancellation I was offered to join ongoing boarding to FLL so I had to change all my traveling plans, have lost my car reservation and a payed spot at the meeting I was going for to begin with! I had to no show to my flight back, because it was from different airport again!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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