$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 5/4. 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$352
Nassau
Nassau1 stop$567
Simpson Bay
Simpson Bay1 stop$637
Bridgetown
Bridgetown1 stop$667
Willemstad
Willemstad2 stops$702
St. John's
St. John's1 stop$728
Montego Bay
Montego Bay1 stop$352
Nassau
Nassau1 stop$567
Simpson Bay
Simpson Bay1 stop$637
Bridgetown
Bridgetown1 stop$667
Willemstad
Willemstad2 stops$702
St. John's
St. John's1 stop$728

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

Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
7:33 pm - 9:25 am
TLH
-
MBJ
14h 52m
1 stop
American Airlines Logo
2:30 pm - 11:57 pm
MBJ
-
TLH
8h 27m
1 stop
$352American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
6:43 pm - 12:03 pm
TLH
-
MBJ
18h 20m
2 stops
American Airlines Logo
1:35 pm - 9:24 am
MBJ
-
TLH
18h 49m
2 stops
$357American Airlines
Mon, May 4 - Thu, May 7
American Airlines Logo
8:15 pm - 11:35 am
TLH
-
STT
15h 20m
1 stop
American Airlines Logo
2:05 pm - 7:45 pm
STT
-
TLH
5h 40m
1 stop
$390American Airlines
Sun, Apr 19 - Thu, Apr 23
American Airlines Logo
6:09 am - 6:10 pm
TLH
-
SJU
12h 01m
1 stop
American Airlines Logo
1:31 pm - 11:56 pm
SJU
-
TLH
10h 25m
1 stop
$426American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
7:33 pm - 9:25 am
TLH
-
MBJ
14h 52m
1 stop
American Airlines Logo
2:30 pm - 11:36 am
MBJ
-
TLH
20h 06m
2 stops
$427American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
7:33 pm - 9:25 am
TLH
-
MBJ
14h 52m
1 stop
American Airlines Logo
12:47 pm - 12:59 pm
MBJ
-
TLH
23h 12m
1 stop
$430American Airlines
Sat, Jun 13 - Tue, Jun 23
American Airlines Logo
8:18 pm - 9:39 am
TLH
-
SJU
13h 21m
1 stop
American Airlines Logo
7:15 pm - 9:02 am
SJU
-
TLH
13h 47m
1 stop
$436American Airlines
Fri, May 22 - Fri, May 29
American Airlines Logo
8:32 pm - 1:08 pm
TLH
-
MBJ
17h 36m
1 stop
American Airlines Logo
5:17 pm - 9:00 am
MBJ
-
TLH
14h 43m
1 stop
$448American Airlines
Tue, May 5 - Fri, May 8
Delta Logo
3:46 pm - 11:13 pm
TLH
-
SJU
7h 27m
1 stop
Delta Logo
6:15 am - 1:57 pm
SJU
-
TLH
7h 42m
1 stop
$476Delta
Tue, May 19 - Sat, May 23
Delta Logo
2:43 pm - 8:30 pm
TLH
-
SJU
5h 47m
1 stop
Delta Logo
7:30 am - 1:58 pm
SJU
-
TLH
6h 28m
1 stop
$511Delta
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 $490, 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 $501 (return) on average. On the other hand, the most expensive months are May and April, when the average cost of round-trip tickets is $832 and $819 respectively.

Good to know

Low seasonFebruary
Cheapest flight$268
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 1% 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.

Reviews of the top airline 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.
7.1
American AirlinesOverall score based on 11563 reviews
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
6.9Entertainment
Airline reviews

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

6.0 GoodJeffrey, Apr 2026
MIA - PIT
Read more American Airlines reviews

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

The flight attendant in business class was excellent! Professional, friendly and attentive.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports