$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 1/6. 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

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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$561
Nassau
Nassau1 stop$560
Simpson Bay
Simpson Bay2 stops$3,978
Bridgetown
Bridgetown1 stop$574
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$560
Simpson Bay
Simpson Bay2 stops$3,978
Bridgetown
Bridgetown1 stop$574

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, Jan 9 - Tue, Jan 13
American Airlines Logo
6:15 am - 6:22 pm
TLH
-
SJU
11h 07m1 stop
American Airlines Logo
5:51 pm - 11:57 pm
SJU
-
TLH
7h 06m1 stop
$405American Airlines
Fri, Mar 6 - Sat, Mar 7
American Airlines Logo
6:13 am - 6:08 pm
TLH
-
SJU
10h 55m1 stop
American Airlines Logo
1:30 am - 12:31 pm
SJU
-
TLH
12h 01m1 stop
$415American Airlines
Tue, Dec 30 - Thu, Jan 1
American Airlines Logo
8:58 pm - 1:41 pm
TLH
-
SJU
15h 43m1 stop
American Airlines Logo
10:03 pm - 9:07 am
SJU
-
TLH
12h 04m1 stop
$454American Airlines
Sat, Jan 31 - Tue, Feb 3
American Airlines Logo
6:53 pm - 12:55 pm
TLH
-
PUJ
17h 02m1 stop
American Airlines Logo
4:09 pm - 11:57 pm
PUJ
-
TLH
8h 48m1 stop
$474American Airlines
Sat, Jan 31 - Tue, Feb 3
American Airlines Logo
6:38 pm - 11:54 am
TLH
-
PUJ
16h 16m2 stops
American Airlines Logo
2:51 pm - 11:33 pm
PUJ
-
TLH
9h 42m1 stop
$478American Airlines
Thu, Jan 22 - Wed, Jan 28
Delta Logo
5:30 am - 11:13 am
TLH
-
MBJ
5h 43m1 stop
Delta Logo
12:38 pm - 10:20 pm
MBJ
-
TLH
9h 42m1 stop
$566Delta
Mon, Jan 19 - Sat, Jan 24
Delta Logo
7:21 am - 3:05 pm
TLH
-
UVF
6h 44m1 stop
Delta Logo
4:25 pm - 9:24 am
UVF
-
TLH
17h 59m1 stop
$644Delta
Thu, Jan 22 - Sun, Jan 25
Delta Logo
5:30 am - 3:18 pm
TLH
-
NAS
9h 48m2 stops
Delta Logo
1:41 pm - 10:20 pm
NAS
-
TLH
8h 39m2 stops
$1,201Delta
Sun, Feb 15 - Thu, Feb 19
WestJet Logo
10:24 am - 3:40 pm
TLH
-
NAS
29h 16m2 stops
WestJet Logo
11:20 am - 4:35 pm
NAS
-
TLH
29h 15m2 stops
$1,562WestJet
Sun, Feb 15 - Thu, Feb 19
WestJet Logo
5:30 am - 7:40 pm
TLH
-
NAS
14h 10m2 stops
WestJet Logo
8:30 pm - 9:42 am
NAS
-
TLH
37h 12m2 stops
$1,569WestJet
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 February, when tickets cost $399 (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 $680 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.

Good to know

Low seasonFebruary
Cheapest flight$233
Best time to beat the crowds with an average 15% 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 8007 reviews
7.9Entertainment
8.5Crew
7.3Food
8.1Boarding
7.9Comfort
Airline reviews

The food is terrible. The staff is wonderful. Comfort is good.

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

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.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

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

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

Information on your arrival and departure airports