$233 Find Cheap Flights from Tallahassee to Caribbean

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 9/20. 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

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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$565
Nassau
Nassau1 stop$510
Simpson Bay
Simpson Bay1 stop$533
Bridgetown
Bridgetown1 stop$601
Willemstad
Willemstad1 stop$550
St. John's
St. John's1 stop$652
Montego Bay
Montego Bay1 stop$565
Nassau
Nassau1 stop$510
Simpson Bay
Simpson Bay1 stop$533
Bridgetown
Bridgetown1 stop$601
Willemstad
Willemstad1 stop$550
St. John's
St. John's1 stop$652

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

Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
5:35 pm - 11:37 pmTLH-SJU
6h 02m1 stop
American Airlines Logo
7:05 pm - 10:14 amSJU-TLH
15h 09m1 stop
$365American Airlines
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Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
6:45 pm - 11:11 amTLH-SJU
16h 26m2 stops
American Airlines Logo
7:05 pm - 10:14 amSJU-TLH
15h 09m1 stop
$390American Airlines
Find Deal
Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
6:31 pm - 11:11 amTLH-SJU
16h 40m2 stops
American Airlines Logo
12:01 pm - 5:03 pmSJU-TLH
5h 02m1 stop
$415American Airlines
Find Deal
Sun, Aug 24 - Fri, Aug 29
American Airlines Logo
5:45 am - 6:15 pmTLH-SJU
12h 30m2 stops
American Airlines Logo
7:05 pm - 9:25 amSJU-TLH
14h 20m1 stop
$425American Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
Delta Logo
7:30 am - 4:33 pmTLH-MBJ
9h 03m1 stop
Delta Logo
3:38 pm - 11:56 pmMBJ-TLH
8h 18m1 stop
$790Delta
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Tue, Dec 16 - Mon, Dec 22
Delta Logo
5:40 am - 4:33 pmTLH-MBJ
10h 53m1 stop
Delta Logo
12:35 pm - 8:50 pmMBJ-TLH
8h 15m1 stop
$815Delta
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Tue, Dec 16 - Sun, Dec 21
WestJet Logo
5:10 pm - 7:23 pmTLH-MBJ
26h 13m2 stops
WestJet Logo
1:25 pm - 12:25 pmMBJ-TLH
23h 00m2 stops
$1,277WestJet
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Thu, Dec 4 - Mon, Dec 8
WestJet Logo
7:15 pm - 1:54 pmTLH-MBJ
18h 39m2 stops
WestJet Logo
7:25 pm - 4:35 pmMBJ-TLH
21h 10m2 stops
$1,585WestJet
Find Deal
Mon, Dec 22 - Tue, Dec 30
LATAM Airlines Logo
5:26 pm - 3:15 pmTLH-PUJ
20h 49m2 stops
LATAM Airlines Logo
2:45 am - 11:56 pmPUJ-TLH
22h 11m2 stops
$3,813LATAM Airlines
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Sat, Sep 13 - Fri, Sep 19
LATAM Airlines Logo
5:09 pm - 3:20 pmTLH-PUJ
22h 11m2 stops
LATAM Airlines Logo
2:45 am - 9:25 amPUJ-TLH
30h 40m2 stops
$3,916LATAM Airlines
Find Deal
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 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 $635 respectively.

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

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

For Tallahassee to Caribbean, Sunday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Caribbean back to Tallahassee, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

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, 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, you should book around 3 weeks before departure, which saves you about 19% 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$233
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 3% 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.

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

    The cheapest time of day to fly to Caribbean 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 is generally at night, which is peak travel time and where the average cost of a ticket is $540.

Reviews of the top 3 airlines serving 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.
8.0
DeltaOverall score based on 7980 reviews
7.3Food
7.9Entertainment
8.2Boarding
8.5Crew
7.9Comfort
Airline reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

2.0 MediocreRosa, Jul 2025TPA - JFK
Read more Delta reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

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.

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.

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

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