$261 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 7/7. 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$536
Simpson Bay
Simpson Bay1 stop$642
Bridgetown
Bridgetown2 stops$706
Willemstad
Willemstad2 stops$609
St. John's
St. John's1 stop$666
Montego Bay
Montego Bay1 stop$352
Nassau
Nassau1 stop$536
Simpson Bay
Simpson Bay1 stop$642
Bridgetown
Bridgetown2 stops$706
Willemstad
Willemstad2 stops$609
St. John's
St. John's1 stop$666

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
7:47 pm - 11:19 am
TLH
-
MBJ
16h 32m
1 stop
American Airlines Logo
5:13 pm - 9:15 am
MBJ
-
TLH
15h 02m
1 stop
$352American Airlines
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
7:47 pm - 11:19 am
TLH
-
MBJ
16h 32m
1 stop
American Airlines Logo
12:38 pm - 9:15 am
MBJ
-
TLH
19h 37m
2 stops
$357American Airlines
Mon, May 11 - Thu, May 14
American Airlines Logo
7:54 pm - 11:24 am
TLH
-
MBJ
16h 30m
1 stop
American Airlines Logo
12:56 pm - 11:56 pm
MBJ
-
TLH
10h 00m
1 stop
$363American Airlines
Tue, May 5 - Tue, May 12
American Airlines Logo
7:06 pm - 3:37 pm
TLH
-
MBJ
21h 31m
2 stops
American Airlines Logo
4:37 pm - 1:05 pm
MBJ
-
TLH
19h 28m
2 stops
$368American Airlines
Thu, May 14 - Thu, May 21
American Airlines Logo
5:33 pm - 11:51 am
TLH
-
MBJ
19h 18m
2 stops
American Airlines Logo
5:17 pm - 11:59 pm
MBJ
-
TLH
5h 42m
1 stop
$392American Airlines
Thu, Aug 6 - Mon, Aug 10
Multiple Airlines Logo
8:08 am - 4:34 pm
TLH
-
SJU
8h 26m
1 stop
Multiple Airlines Logo
3:06 am - 1:37 pm
SJU
-
TLH
10h 31m
2 stops
$423Multiple Airlines
Sat, Jul 11 - Sun, Jul 19
Delta Logo
3:23 pm - 10:29 pm
TLH
-
SJU
7h 06m
1 stop
Delta Logo
7:30 am - 6:16 pm
SJU
-
TLH
10h 46m
1 stop
$506Delta
Sun, Jul 19 - Sat, Jul 25
Multiple Airlines Logo
12:47 pm - 1:48 pm
TLH
-
PUJ
25h 01m
1 stop
Multiple Airlines Logo
2:58 pm - 7:28 am
PUJ
-
TLH
16h 30m
1 stop
$537Multiple Airlines
Sat, May 16 - Fri, May 22
Delta Logo
6:15 am - 1:56 pm
TLH
-
CUR
7h 41m
1 stop
Delta Logo
3:16 pm - 10:42 pm
CUR
-
TLH
7h 26m
1 stop
$654Delta
Fri, Jul 24 - Fri, Jul 31
WestJet Logo
3:23 pm - 11:10 am
TLH
-
NAS
19h 47m
2 stops
WestJet Logo
12:00 pm - 4:50 pm
NAS
-
TLH
28h 50m
2 stops
$1,173WestJet
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 $442, 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
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 3% increase in price.

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 11659 reviews
6.4Food
6.9Entertainment
7.9Crew
7.2Comfort
7.5Boarding
Airline reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

4.0 OkayAnonymous, Apr 2026
MIA - UIO
Read more American Airlines reviews

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports