$193 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 5/1. 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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Flight Deals

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 Bay2 stops$357
Nassau
Nassau1 stop$571
Saint Thomas Island
Saint Thomas Island2 stops$489
Simpson Bay
Simpson Bay1 stop$642
Providenciales
Providenciales1 stop$610
Bridgetown
Bridgetown2 stops$722
George Town
George Town1 stop$831
Willemstad
Willemstad1 stop$709
St. John's
St. John's1 stop$681
Montego Bay
Montego Bay2 stops$357
Nassau
Nassau1 stop$571
Saint Thomas Island
Saint Thomas Island2 stops$489
Simpson Bay
Simpson Bay1 stop$642
Providenciales
Providenciales1 stop$610
Bridgetown
Bridgetown2 stops$722
George Town
George Town1 stop$831
Willemstad
Willemstad1 stop$709
St. John's
St. John's1 stop$681

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

So, Jun 7 - Do, Jun 11
American Airlines Logo
7:48 pm - 11:45 am
TLH
-
MBJ
16h 57m
2 stops
American Airlines Logo
2:08 pm - 11:20 am
MBJ
-
TLH
20h 12m
2 stops
$357American Airlines
Fr, Mai 8 - Fr, Mai 15
Delta Logo
8:05 am - 3:34 pm
TLH
-
MBJ
8h 29m
1 stop
Delta Logo
1:18 pm - 8:43 pm
MBJ
-
TLH
6h 25m
1 stop
$387Delta
Fr, Mai 8 - Fr, Mai 15
American Airlines Logo
7:54 pm - 11:51 am
TLH
-
MBJ
16h 57m
2 stops
American Airlines Logo
4:37 pm - 11:42 am
MBJ
-
TLH
18h 05m
2 stops
$392American Airlines
Mi, Mai 6 - So, Mai 10
American Airlines Logo
6:09 am - 3:37 pm
TLH
-
MBJ
10h 28m
1 stop
American Airlines Logo
4:37 pm - 1:05 pm
MBJ
-
TLH
19h 28m
2 stops
$402American Airlines
Mi, Mai 6 - So, Mai 10
American Airlines Logo
6:09 am - 3:37 pm
TLH
-
MBJ
10h 28m
1 stop
American Airlines Logo
4:37 pm - 9:20 am
MBJ
-
TLH
15h 43m
1 stop
$406American Airlines
Mo, Apr 20 - Sa, Apr 25
American Airlines Logo
8:15 pm - 9:13 am
TLH
-
SJU
12h 58m
1 stop
American Airlines Logo
1:31 pm - 11:56 pm
SJU
-
TLH
10h 25m
1 stop
$426American Airlines
Do, Jul 2 - Di, Jul 7
Multiple Airlines Logo
12:47 pm - 3:58 pm
TLH
-
SJU
27h 11m
1 stop
Multiple Airlines Logo
5:01 pm - 7:28 am
SJU
-
TLH
38h 27m
2 stops
$428Multiple Airlines
Mi, Apr 22 - Mo, Apr 27
American Airlines Logo
9:50 am - 6:10 pm
TLH
-
SJU
8h 20m
1 stop
American Airlines Logo
7:00 pm - 9:20 am
SJU
-
TLH
14h 20m
1 stop
$431American Airlines
Mi, Mai 6 - So, Mai 10
American Airlines Logo
7:54 pm - 11:51 am
TLH
-
MBJ
16h 57m
2 stops
American Airlines Logo
12:25 pm - 9:20 am
MBJ
-
TLH
19h 55m
2 stops
$437American Airlines
Fr, Mai 15 - Mo, Mai 18
Delta Logo
6:15 am - 4:35 pm
TLH
-
NAS
10h 20m
1 stop
Delta Logo
6:00 pm - 10:42 pm
NAS
-
TLH
4h 42m
1 stop
$606Delta
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 $478, 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 November, when tickets cost $465 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $680 and $665 respectively.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$193
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Tallahassee to Montego Bay

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 11520 reviews
7.9Crew
7.5Boarding
6.9Entertainment
6.4Food
7.2Comfort
Airline reviews

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

10.0 ExcellentTy, Mar 2026
MIA - DFW
Read more American Airlines reviews

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.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Tallahassee (TLH)