$313 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 11/20. 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$535
Nassau
Nassau1 stop$475
Simpson Bay
Simpson Bay1 stop$897
Providenciales
Providenciales1 stop$572
Bridgetown
Bridgetown1 stop$596
George Town
George Town1 stop$590
Willemstad
Willemstad1 stop$562
Montego Bay
Montego Bay1 stop$535
Nassau
Nassau1 stop$475
Simpson Bay
Simpson Bay1 stop$897
Providenciales
Providenciales1 stop$572
Bridgetown
Bridgetown1 stop$596
George Town
George Town1 stop$590
Willemstad
Willemstad1 stop$562

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

Tue, Feb 24 - Thu, Feb 26
Delta Logo
7:30 am - 5:12 pmTLH-SJU
8h 42m1 stop
Delta Logo
7:30 am - 2:46 pmSJU-TLH
8h 16m1 stop
$365Delta
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Tue, Dec 30 - Thu, Jan 1
American Airlines Logo
8:58 pm - 9:36 amTLH-SJU
11h 38m1 stop
American Airlines Logo
10:26 am - 8:28 pmSJU-TLH
11h 02m1 stop
$425American Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
American Airlines Logo
8:04 pm - 11:45 amTLH-SJU
14h 41m1 stop
American Airlines Logo
6:50 pm - 1:15 pmSJU-TLH
19h 25m2 stops
$468American Airlines
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Tue, Feb 24 - Thu, Feb 26
American Airlines Logo
12:21 pm - 11:20 pmTLH-SJU
9h 59m2 stops
American Airlines Logo
12:50 pm - 12:24 amSJU-TLH
12h 34m1 stop
$473American Airlines
Find Deal
Tue, Dec 30 - Thu, Jan 1
American Airlines Logo
8:58 pm - 9:36 amTLH-SJU
11h 38m1 stop
American Airlines Logo
10:26 am - 8:28 pmSJU-TLH
11h 02m1 stop
$507American Airlines
Find Deal
Sun, Mar 1 - Fri, Mar 6
American Airlines Logo
8:43 pm - 12:10 pmTLH-STT
14h 27m1 stop
American Airlines Logo
6:40 pm - 10:35 amSTT-TLH
16h 55m2 stops
$519American Airlines
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
5:35 am - 12:40 pmTLH-MBJ
7h 05m1 stop
Delta Logo
2:15 pm - 2:46 pmMBJ-TLH
24h 31m2 stops
$535Delta
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Fri, Dec 5 - Mon, Dec 8
WestJet Logo
7:08 pm - 1:54 pmTLH-MBJ
18h 46m2 stops
WestJet Logo
7:25 pm - 6:22 pmMBJ-TLH
22h 57m2 stops
$1,032WestJet
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Fri, Dec 5 - Mon, Dec 8
WestJet Logo
5:07 pm - 1:54 pmTLH-MBJ
20h 47m2 stops
WestJet Logo
7:25 pm - 6:22 pmMBJ-TLH
22h 57m2 stops
$1,064WestJet
Find Deal
Wed, Nov 26 - Sun, Nov 30
WestJet Logo
1:39 pm - 1:54 pmTLH-MBJ
24h 15m2 stops
WestJet Logo
8:25 pm - 6:18 pmMBJ-TLH
21h 53m2 stops
$1,142WestJet
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 $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?

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 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$313
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 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.
7.9
DeltaOverall score based on 7954 reviews
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
Airline reviews

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

8.0 ExcellentOlaf, Sep 2025FLL - ATL
Read more Delta reviews

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

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.

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.

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

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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