$365 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 12/30. 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

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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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$561
Nassau
Nassau1 stop$472
Simpson Bay
Simpson Bay2 stops$3,629
Bridgetown
Bridgetown2 stops$571
George Town
George Town1 stop$940
Montego Bay
Montego Bay1 stop$561
Nassau
Nassau1 stop$472
Simpson Bay
Simpson Bay2 stops$3,629
Bridgetown
Bridgetown2 stops$571
George Town
George Town1 stop$940

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

Mon, Apr 6 - Wed, Apr 8
American Airlines Logo
7:55 pm - 10:35 am
TLH
-
SJU
14h 40m1 stop
American Airlines Logo
3:45 pm - 11:59 pm
SJU
-
TLH
8h 14m1 stop
$365American Airlines
Wed, Feb 4 - Wed, Feb 18
American Airlines Logo
6:00 am - 3:59 pm
TLH
-
SJU
8h 59m2 stops
American Airlines Logo
1:58 pm - 9:32 pm
SJU
-
TLH
8h 34m1 stop
$385American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
8:44 pm - 9:00 am
TLH
-
SJU
12h 16m1 stop
American Airlines Logo
6:55 pm - 9:56 am
SJU
-
TLH
15h 01m1 stop
$390American Airlines
Mon, Jan 26 - Thu, Jan 29
Delta Logo
1:45 pm - 11:45 pm
TLH
-
SJU
9h 00m1 stop
Delta Logo
3:55 pm - 10:20 pm
SJU
-
TLH
7h 25m1 stop
$405Delta
Sun, Apr 5 - Sat, Apr 11
American Airlines Logo
8:44 pm - 9:00 am
TLH
-
SJU
12h 16m1 stop
American Airlines Logo
6:55 pm - 9:56 am
SJU
-
TLH
15h 01m1 stop
$440American Airlines
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
9:59 am - 6:35 pm
TLH
-
NAS
8h 36m1 stop
American Airlines Logo
7:45 am - 6:59 pm
NAS
-
TLH
11h 14m1 stop
$472American Airlines
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
8:09 pm - 11:20 am
TLH
-
NAS
15h 11m2 stops
American Airlines Logo
3:05 pm - 11:59 pm
NAS
-
TLH
8h 54m2 stops
$476American Airlines
Thu, Jan 22 - Wed, Jan 28
Delta Logo
5:30 am - 12:54 pm
TLH
-
MBJ
7h 24m1 stop
Delta Logo
12:38 pm - 10:20 pm
MBJ
-
TLH
9h 42m1 stop
$566Delta
Wed, Jun 3 - Sat, Jun 6
LATAM Airlines Logo
1:00 pm - 3:20 pm
TLH
-
PUJ
26h 20m2 stops
LATAM Airlines Logo
5:50 pm - 12:04 pm
PUJ
-
TLH
18h 14m2 stops
$1,553LATAM Airlines
Mon, Feb 23 - Thu, Feb 26
WestJet Logo
5:30 am - 2:46 pm
TLH
-
UVF
32h 16m2 stops
WestJet Logo
3:40 pm - 6:40 pm
UVF
-
TLH
28h 00m2 stops
$3,799WestJet
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 $452, 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 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 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.

Good to know

Low seasonFebruary
Cheapest flight$283
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 5% 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 11052 reviews
7.2Comfort
6.9Entertainment
7.5Boarding
6.4Food
8.0Crew
Airline reviews

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

4.0 OkayGabriel, Dec 2025
MIA - EZE
Read more American Airlines reviews

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

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.

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